Holiday Fireworks and Drone Dinner Cruises - December: Enjoy a chef-prepared dinner menu, fully stocked bar, and DJ while soaking in Chicago views from a climate-controlled interior and open-air rooftop decks. Near the end of the cruise, the sky will illuminate with Navy Pier’s fireworks or a modern glowing drone show. Secure your tickets via City Cruises Chicago's website.
Christmas Eve and Christmas Day Brunch & Dinner Cruises – December 24 and 25: City Cruises' DJ will create the ambiance while the city lights will light up the night and offer vantage points of the Chicago skyline. This cruise will be paired with chef-prepared menus and crafted seasonal cocktails. Visit City Cruises Chicago's website to reserve.
Prime & Provisions
The supper club-inspired steakhouse will open on Christmas Eve to serve their holiday tasting menu for $110 per person and will include steak and seafood dishes for each course and the option to add on classic sides. A variety of desserts are also included in the menu, and diners can add a beverage pairing to the experience for $49. Reservations are available on Christmas Eve from 4 p.m. - 9 p.m. Reservations can be made on their website.
Cindy's Rooftop
This festive season, Cindy's Rooftop invites guests to dine high above the city with a Christmas Eve special. Cindy's Rooftop will feature a seasonally inspired menu with elevated takes on classic holiday dishes, crafted by the culinary team, led by Executive Chef Kaleena Bliss. Christmas Eve Dinner Specials include a Chilled Seafood Platter, 12oz Prime Rib and Buche De Noel.
Miss Ricky's
Seven Fishes Dinner at Miss Ricky’s: From December 14-24, indulge in the Seven Fishes dinner, featuring seafood specials like charred Spanish octopus, grilled whole branzino, and seared scallops. You can enjoy these dishes á la carte or opt for a family-style feast for $85 per person. Reservations are not required, but are highly encouraged.
Elf Spaghetti at Miss Ricky’s: This holiday season, Miss Ricky’s is bringing back the Candy-Filled Elf Spaghetti, inspired by the classic movie Elf. Executive Chef Mike Alaridi has reimagined this dish, combining crispy sweet spaghetti with Buddy’s favorite dessert toppings—M&M’s, chocolate syrup, raspberry sauce, marshmallows, vanilla ice cream, chocolate wafers, and a generous drizzle of maple syrup, available throughout the month of December.
Petterino’s
Petterino’s has announced new drink specials and extended hours for the holiday season and the Christkindlmarket!
Holiday Cocktails at Petterino’s and Pasticceria: Starting Monday, Nov. 18, they'll be offering the following specialty drinks for both dine-in at Petterino’s and to-go at Petterino’s Pasticceria: Jesse’s House Made Nogg and Petterino’s House Made Hot Apple Cider. Hot Chocolate Selections include Original, Peppermint, Gingerbread and Vanilla Caramel. All hot chocolates will have the option to be spiked with alcohol for an extra $8!
Extended Hours: To better serve guests during the Christkindlmarket and Christmas festivities, extended hours for Petterino's starts November 18th. They'll be open on Monday until 9 p.m., Tuesday – Thursday until 10 p.m., Friday and Saturday until 11 p.m. and Sunday until 8 p.m. Petterino’s Pasticceria extended hours start Saturday, Nov. 23). Monday – Friday they will be open from 8 a.m. to 8 p.m. and on Saturday and Sunday from 11 a.m to 6 p.m.
Live Jazz Music at Petterino’s:
Additionally, starting Monday, Nov. 18, they’ll be offering live jazz music every Monday at 6:30 p.m.
Mercat a la Planxa
The Blackstone Hotel welcomes families to meet Santa Claus and the Grinch in the hotel's lobby on December 15. From 10 a.m. to noon, guests can capture holiday photos with the duo. After the photo opportunity, families are invited to Mercat a la Planxa for a special brunch. Children can enjoy complimentary cookies and hot chocolate, while adults indulge in festive cocktail specials. The regular brunch menu will be available, featuring Mercat's signature Spanish-inspired dishes made with fresh, local ingredients.
Photo courtesy of City Cruises Chicago
Fulton Market/West Loop
Punch Bowl Social
Punch Bowl Social welcomes The Ugly Christmas Sweater Shop for a limited-time holiday pop-up series. The pop-up will run Friday, Nov. 15, through Tuesday, Dec. 24 during Punch Bowl Social’s regular business hours, Sundays through Thursdays from 11 a.m. – 11 p.m., and Fridays and Saturdays from 11 a.m. – 1 a.m. Guests can peruse an assortment of upcycled and brand new holiday sweaters, ranging in price from $14.99 to $39.99, while sampling new seasonal craft cocktails and shareable dishes, as well as enjoying holiday décor and games including bowling, karaoke, dartsee, arcade games and more. The Ugly Christmas Sweater Shop was founded by Dallas-based vintage clothing guru Jeremy Turner in 2013 after he noticed a demand for the garments at his mobile thrift store. It took a multi-year hiatus during COVID and was relaunched at Punch Bowl Social Dallas in 2023. This year in addition to Dallas, it expands to Chicago and Austin for the first time.
In addition to the array of festive fashions, guests can enjoy the new menu of specialty craft cocktails, zero proof and punch, including To Me, You are Perfect, a fruit-forward punch served by the bowl or single cup; We Slept In!, a twist on the classic margarita; I Triple-Dog-Dare Ya, an old fashioned served with Ralphie glasses and a pickled filthy cherry and Son of a Nutcracker, anespresso martini also available in a N/A version, along with a variety of scratch-made eats. For those looking to host a private event this year, Punch Bowl Social can accommodate groups of all sizes in its versatile party spaces, while offering customizable menus of bites and libations.
Fioretta
The Italian Steakhouse from DineAmic Hospitality will open on Christmas Eve to serve a special tasting menu for $110 per person that brings a variety of offerings. Diners can add on a curated beverage pairing option for $49. Reservations are available on Christmas Eve from 4 p.m. - 9 p.m., Reservations can be found on their website.
La Serre
La Serre will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
Bar La Rue
Bar La Rue will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
LYRA
LYRA will be open for a la carte business on Christmas Eve, and reservations are now available on their website.
Photo courtesy of Punch Bowl Social
Gold Coast
Pippin's Lounge and Pippin's Tavern
The Pippin’s Lounge, a new piano bar tucked behind Pippin’s Tavern’s staircase transforms into a holiday-themed Tinsel & Tunes pop-up. Join Pippin’s Tavern every Friday and Saturday from 9pm to 1am for live dueling piano shows with a yuletide twist. Resident piano performers will play holiday tunes and Christmas carols to soak in the merriment all season long. With holiday decor, seasonal drinks and food, Pippin’s pianists will take audience requests with high-octane holiday singalongs.
Pippin's Tavern is also transforming into a winter wonderland this December! With festive decorations adorning the venue, the establishment invites all to revel in the holiday spirit. Guests can savor the season with specialty holiday cocktails, holiday beers on tap, and specials available in December. Guests are invited to stop in all season long for Happy Hour every Monday through Friday from 3pm to 6pm for $1.50 oysters, $6 draft beer, $6 draft wine, and BOGO small shares.
Sofitel Chicago
Located in the Magnificent Mile area, the hotel is offering several holiday offers and activations for locals and visitors alike.
Festive Holiday Dinner: Join Sofitel Chicago on Dec. 11 at 6 p.m. for its annual festive holiday dinner! With a focus on champagne pairings, the multi-course dinner is $99 per person and reservations can be made on Tock.
Festive Afternoon Tea: The hotel reimagined their tea service to help visitors and locals alike feel the festive spirit! Indulge in the tea service, but with a holiday twist. The new menu includes pastries and treats such as cranberry scones, Choux Puffs with Truffle Cream, Cranberry Scones, Eggnog Mousse and more! Make a reservation at Le Bar on Sofitel's website.
Winter Menu at Le Bar: In honor of the winter season, the hotel’s bar, Le Bar, rolled out several new cocktails inspired by it: McCalister Mule - bombay sapphire gin, koval cranberry liqueur, grenadine; Noel Royale - remy martin vsop, crème de cassis, faire la fete brut; Fireside Old Fashioned - maker’s mark, house bitters, spiced demera syrup, brown butter; PSL Season - bacardi spiced rum, pumpkin pie syrup, lemon juice, egg white; and Sweater Weather (Mocktail) - Seedlip Spice 94, spiced demerara, ginger beer, fresh lemon.
Adorn at Four Seasons Hotel Chicago
This holiday season, Four Seasons Hotel Chicago has partnered with Justice of the Pies for a Holiday Gift Shop & Pop-Up. From November 24 through December 25, guests can explore an exclusive selection of holiday pies, gift boxes, special merchandise, and more. Adorn Bar at Four Seasons will host a "Pies & Pours" experience, pairing signature Justice of the Pies treats with crafted cocktails by lead bartender Adam Chase. Guests can savor a slice of pie alongside a duo of hand-crafted cocktails (available for dinner only). Pairings include: Michigan Cherry Cheesecake paired with a Mezcal Last Word, Chocolate Espresso Cake paired with a Carajillo Espresso Martini and Blue Cheese Pear Praline Tart Tatin paired with a Spiced Cranberry French 75.
Guests can enjoy a slice and a sip duo for ($40), or indulge in the full experience for ($70), which also includes a signed cookbook. Additionally, from November 24 through December 25, these pies will be available on the Adorn Restaurant menu for a la carte ordering. In addition to the Pies & Pours experience, Adorn Restaurant will serve quiche options by Justice of the Pies for brunch. A curated collection of Justice of the Pies merchandise will be available for purchase in the hotel lobby.
Photo courtesy of Pippin's Tavern
Lakeview
Big Star Wrigleyville
Inspired by Chappell Roan’s “Pink Pony Club”, the Big Star crew is decking their halls with glittery hanging ornaments, a Christmas tree dressed up in pink cowboy hats, and a new lineup of food & drink specials. Look out for limited-time menu items including the Smokey Brisket Nachos ($18) with beef brisket, cheesy nacho sauce, salsa seca, pico de gallo, black beans, and guacamole and Cowboy Coffee ($12), a caffeine kick with a sweet finish featuring La Colombe Cold Brew, cinnamon honey, Buffalo Trace Cream, and bourbon, garnished with whipped vanilla cream, a candy cane, and sprinkles. The pop-up will expand on its normal catalog of cowboy classics with a heavy emphasis on Christmas tunes combined with modern country-infused classics— think Beyonce’s Cowboy Carter and Shaboozey. Classic holidays songs from Dolly Parton and Taylor Swift can also be expected.
Lincoln Park
River Shannon
River Shannon is celebrating the season with holiday decor, festive drinks, holiday beers on tap, and holiday-themed treats for all furry visitors. From the holiday menu, guests can choose from classic drinks with a holiday twist like the Claus-Mopolitan, Polar Paloma, Mistletoe Mule, Rudolph’s Old Fashioned and more. Known for its array of board games onsite, guests can also expect Holiday Game Nights at River Shannon, featuring holiday board games galore. Upcoming holiday-themed events:
Cookies & Cocoa: Every Monday in December from 4 p.m. to 6 p.m., guests can unleash their inner cookie artist during a festive afternoon of cookie decorating. River Shannon provides all the cookies, icing, and festive toppings needed to create edible masterpieces. Visitors can also purchase a boozy hot cocoa from the holiday drink menu and decorate with toppings from the Boozy Hot Cocoa Bar.
Dog Photos with Santa: Santa Claus is coming to River Shannon! Patrons can stop in with their furry friends on Sunday, December 1 and Sunday, December 15 from 12pm to 3pm for a complimentary photo opp with Santa.
Margaritaville is inviting guests to its Holiday Pop-Up Bar from Friday, Nov. 15 to Sunday, Jan. 5. to enjoy holiday décor, drinks and activities. Margaritaville is transforming into a festive winter paradise, with holiday decorations and a seasonal ambiance. It is also putting an island twist on classic holiday flavors with five original drinks including Winter Wave and Deck the Palms, which will be served in limited-edition collectible ornament cups:
Sleigh Ride – A mix of Fireball Whiskey, Margaritaville Passionfruit Tequila, tart cranberry, and a splash of lemon with a hint of holiday spice.
Beachside Grinch – This concoction blends melon liqueur, Parrot Bay Coconut, and a festive kick of Fireball Whiskey. Topped with a cranberry float.
Kringle & Coke – Crème de menthe and crème de cocoa are matched with Parrot Bay Spiced Rum, lemon, and classic Coca-Cola.
Winter Wave – This blend of Basil Hayden bourbon and Grand Marnier is sweetened with coconut syrup and balanced by the tang of lime and cranberry juice.
Deck the Palms – With Espolon Blanco Tequila, a splash of Grand Marnier, and creamy Pina Colada mix, A splash of cranberry juice adds a touch of red.
Old Town
The Lodge Tavern
The Lodge Tavern is transforming into a holiday wonderland complete with twinkling lights, wreaths, garland, and more. From the holiday menu, guests can choose from festive riffs on classic cocktails like Mule-Tide Greetings, Ebenezer’s Old Fashioned, Mrs. Clausmo and more. And for those looking to warm their bellies, The Lodge Tavern will offer a hot cocktail menu featuring the Ho Ho Hot Toddy, Irish You A Merry Christmas, St. Nicks Cider, holiday beers on tap, and more.
Dog Photos with Santa: Santa Claus is coming to The Lodge Tavern! Patrons can stop in with their furry friend on Sunday, December 15 from 12pm to 3pm for a complimentary photo opp with Santa.
She-Nannigans
All December long, guests are invited to celebrate the season with games galore during Holiday Game Nights. She-nannigans will be decked out in decor and will feature holiday-themed board games, in addition to darts, pop-o-shot, pong, and giant Jenga. And, of course, no holiday gathering is complete without seasonal drinks. She-nannigans will feature a special holiday menu with seasonal twists on classic cocktails.
Every Thursday through Sunday starting at 5 p.m., She-nannigans DJ will be spinning festive tunes and party hits. Guests are also invited to take center stage every Thursday evening at She-nannigans for Holiday Carol-oke starting at 8pm. And on Friday, December 20 at 7pm, guests are invited to dust off their quirkiest holiday sweater and join She-nannigans for an Ugly Sweater Holiday Party!
Photo courtesy of The Lodge Tavern
River North
Three Dots and a Dash
Three Dots and a Dash launches their River North Pole bar takeover beginning November 15. The team of the River North cocktail bar is transforming their space from the sandy beaches of a tropical paradise into a snowy winter wonderland escape all holiday season long. Complete with winter and holiday decorations throughout the space, a dedicated specialty holiday cocktail menu with both hot cocktails and themed sippers that also feature the same glassware and mugs as their traditional menu (even a speciality Snowman mug for all holiday mug collectors), Three Dots is a place to celebrate this time of year with friends, family and out of town visitors. Plus, the team’s retail program is available and open in the bar daily providing a one-stop-shop for holiday gift giving, particularly for those cocktail connoisseurs.
Nonnina
With the holiday season approaching, Nonnina offers an exclusive and interactive 5-course Chef’s Table Experience, for holiday dining with friends and family. During the experience, Executive Chef John Boudouvas crafts a customized 5-course tasting menu tailored to your preferences. He then guides you through each course, explaining the inspiration behind the dishes and the carefully selected premium wine pairings. The private dining space comfortably accommodates up to 10 guests, which makes it a setting for special occasions and celebrations. For reservations, guests can contact Brian Lachman at brian@nonninachicago.com or call 312-822-0077.
The Redhead Piano Bar
Sing along to your favorite carols at Redhead Piano Bar! The Redhead Piano Bar invites guests to sing along to all the holiday classics with nightly live piano music and performances from 7 p.m. to 4 a.m. The late night spot decked out with garland, lights, and mistletoe will feature a special limited time holiday cocktail menu including Candy Cane with Vanilla Vodka, Bailey’s, and Peppermint Schnapps, Jingle Juice with Bourbon, Cranberry Juice, and Ginger Ale, Kris Kringle Kir Royale with Cranberry Juice, Chambord, and Korbel, and more. Guests who purchase a holiday cocktail in December will receive a raffle ticket for the chance to join The Redhead’s piano player on stage. Each Monday through Thursday at 9 p.m., the piano player will draw a ticket and invite the lucky winner to sing a holiday carol or any song of their choice.
Headquarters Beercade
The Reindeer Games Christmas Pop-Up at Headquarters Beercade launches on Friday, November 22nd with all new Christmas decor and installations, Christmas-themed events, cocktails, and more! Immerse yourself in a holiday wonderland filled with lots of photo opps like a full-sized sleigh as you take a ride through the North Pole. Have a seat on the "Naughty or Nice" throne, and make lots of holiday memories with your crew.
Kinzie Chophouse
Kinzie Chophouse will offer their annual Festive Odyssey tasting menu during the month of December. With eight courses, it's a celebration menu to enjoy over the holiday season with family and friends and offers steak and seafood courses. Kinzie Chophouse's Festive Odyssey tasting menu will be available Fri - Sun evenings throughout December and on Christmas Eve and New Year's Eve from 5 p.m. - 9 p.m. Priced at $150 per person, reservations can be made on their website.
Siena Tavern
Executive Chef Fabio Viviani’s full a la carte menu will be available at Siena Tavern, with the addition of three special holiday preparations this Christmas Eve: lamb cappelletti: pecorino, mint, celery root; berkshire pork loin: charred radicchio, smoked onion soubise, walnut and currant sofrito; and dark chocolate mousse white chocolate peppermint bark, pistachio praline. Reservations are now available on their website.
Brindille
Brindille will be open for Christmas Eve from 4–8 PM where guests can experience "The Winter Réveillon", inspired by the French tradition of Le Réveillon—a celebratory dinner enjoyed on Christmas and New Year’s Eve. The name comes from the French word for "awakening," as these dinners are meant to be savored late into the night. For this special occasion, they're offering both à la carte selections and a prix fixe menu. Reservations can be made on Resy.
Godfrey Hotel Chicago
On Christmas Eve, Dec. 24, the Godfrey Hotel Chicago will host a festive brunch with Santa from 11 a.m. to 4 p.m. The brunch buffet will feature breakfast classics, a carving station with prime rib, and sweet offerings — like pancakes and French toast, plus, an avocado toast bar, an acai bowl station, and more. The dessert selections will include Christmas cookies, Santa cake pops, peppermint bark, and hot cocoa. Priced at $49 per adult and $15 for children under 12. Reservations can be made on Tock.
Hard Rock Cafe Chicago
Hard Rock Cafe Chicago invites families to celebrate the holiday season with Breakfast with Santa on Dec. 24, from 11 a.m. to 1 p.m. Guests can enjoy a festive breakfast buffet while meeting Santa Claus and photo opportunities. Tickets are $25 for adults and $13 for children, available on Eventbrite.
Ukrainian Village
Heritage Restaurant & Caviar Bar
Treat yourself to Heritage's Christmas Eve tradition with the Feast of the Seven Fishes tasting. The dinner is 5 courses and includes Smoked Oyster and Cauliflower Tart with Osetra Caviar; Sliced Sashimi of Tuna and Hamachi with Coconut Dashi, Grand Cru Caviar, Cilantro Oil, Crispy Shallots; Steamed Mussels with Apple Cider, Kimchi Polish Sausage and Sourdough; Grill Roasted Red Snapper with Braised Collard Greens and Pimento Grits; and Swordfish au Poivre with Truffle Mash, Bordelaise and Onion Rings. The Feast of the Seven Fishes tasting is $200 per person, with an optional beverage pairing available. Reservations can be made on Tock.
Heritage Restaurant & Caviar Bar also honors Hanukkah again this year with their a la carte take home menu. Heritage's homemade options include: Smoked brisket, smoked & cured fish (including their famous gravlax and pickled herring), latkes, matzo ball soup, and many other Hanukkah-friendly house specialties. Pickup is available Dec 24th through Jan 1st. Pre-orders accepted by phone at 773-661-9577, in-person, and online beginning in early December.
Photo courtesy of The Redhead Piano Bar
Multiple Locations
The Goddess and Grocer
The Goddess and Grocer has catering options for Hanukkah and Christmas this year. The menus offer options for those in need of vegetarian, vegan, gluten-free, and dairy-free options that can be pre-ordered + select items in stores.
The Goddess and Grocer Christmas: For holiday gatherings of any size, The Goddess and Grocer’s Christmas catering menu options include Christmas Dinner for Two $85, Family Matters (serves 6) $225, Ham It Up (serves 6) $225, Vegan Dinner for 2 $85 and a la carte food, wine, and more. The menu also offers options for those in need of vegetarian, vegan, gluten-free, and dairy-free options! The Christmas catering can be ordered at https://www.goddessandgrocer.com. Delivery is available and FREE pickup is available at all locations. Select items from the Christmas menu will be available in stores.
The Goddess and Grocer HANUKKAH: The Goddess and Grocer will offer an a la carte to-go / delivery menu full of twists on the classics with vegetarian, vegan and gluten-free options as well as Sommelier wine selections. To order, please visit GoddessandGrocer.com. Select items will be available in stores for pick up as well. Locations include Fulton Market, River North, Gold Coast, and Bucktown.
Bar Siena
Bar Siena in the West Loop and Skokie will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
Q-BBQ
Enjoy Q-BBQ's seasonal Prime Rib Slices served with Alabama White Sauce and Au Jus, or the Smoked Mashed Potatoes served with Brisket Gravy - for a limited time only! Available Friday through Sunday only from December 6th through December 27th. Online ordering to come.
Christmas Catering for Pick Up Offerings include Slices of Prime Rib; Alabama White Sauce and Au Jus; Whole or Half Prime Rib; Alabama White Sauce and Au Jus; Smoked Mashed Potatoes; and Brisket Gravy. Available to order from Monday, December 6th through December 18th. Online ordering link to come. Pick Up: Monday, December 23rd and Tuesday, December 24th.
Suburbs
VIOLI
VIOLI will be open for a la carte business on Christmas Eve, and reservations are now available on their website.
Cooper's Hawk Schererville
The newly-opened Cooper's Hawk Schererville invites everyone this Christmas Eve to experience its winery, restaurant, and Napa-style tasting room concept to more guests in the region. Led by a culinary team with Executive Chef Matt McMillin and local culinary leader Nick Gard, guests can enjoy a contemporary-American menu infused with international flavors and wine pairings. Open from 11 a.m. to 9 p.m., the restaurant also features a special Wine O'Clock Happy Hour from 3 to 5 p.m., offering five appetizers and wines by the glass. Reservations can be made online.
Fat Rosie's
Fat Rosie’s opened its newest location in Rosemont in October and has other restaurants throughout the Chicagoland area in Naperville, Schaumburg, Frankfort, Lincolnshire, and Lincolnwood. The team will be hosting its annual Brunch with Santa at all six locations. In addition to holiday music and an appearance from Santa, the team will be offering one complimentary photo per guest, with the option to purchase a larger photo and frame.
Brunch with Santa Schedule: On Sunday, December 1, Santa will be at the Schaumburg and Rosemont locations from 11:00 AM to 3:00 PM. Then on Sunday, December 8, Santa will show at the Lincolnwood and Lincolnshire locations from 11:00 AM to 3:00 PM. Finally, on Sunday, December 15, Santa will be at the Naperville and Frankfort locations from 11:00 AM to 3:00 PM
Other holiday specials include Fat Rosie's Mistletoe Margarita ($15) featuring Casamigos Reposado Cristalino, Peach Liqueur, Cranberry Juice, Citrus, Fresh Cinnamon-Spiced Cranberries, and a Sugar-Tajin rim. Available for the month of December. There will also be a Seasonal menu available until January 5 (not available at Rosemont location).
Downtown/The Loop
Holiday Fireworks and Drone Dinner Cruises - December: Enjoy a chef-prepared dinner menu, fully stocked bar, and DJ while soaking in Chicago views from a climate-controlled interior and open-air rooftop decks. Near the end of the cruise, the sky will illuminate with Navy Pier’s fireworks or a modern glowing drone show. Secure your tickets via City Cruises Chicago's website.
Christmas Eve and Christmas Day Brunch & Dinner Cruises – December 24 and 25: City Cruises' DJ will create the ambiance while the city lights will light up the night and offer vantage points of the Chicago skyline. This cruise will be paired with chef-prepared menus and crafted seasonal cocktails. Visit City Cruises Chicago's website to reserve.
The supper club-inspired steakhouse will open on Christmas Eve to serve their holiday tasting menu for $110 per person and will include steak and seafood dishes for each course and the option to add on classic sides. A variety of desserts are also included in the menu, and diners can add a beverage pairing to the experience for $49. Reservations are available on Christmas Eve from 4 p.m. - 9 p.m. Reservations can be made on their website.
This festive season, Cindy's Rooftop invites guests to dine high above the city with a Christmas Eve special. Cindy's Rooftop will feature a seasonally inspired menu with elevated takes on classic holiday dishes, crafted by the culinary team, led by Executive Chef Kaleena Bliss. Christmas Eve Dinner Specials include a Chilled Seafood Platter, 12oz Prime Rib and Buche De Noel.
Seven Fishes Dinner at Miss Ricky’s: From December 14-24, indulge in the Seven Fishes dinner, featuring seafood specials like charred Spanish octopus, grilled whole branzino, and seared scallops. You can enjoy these dishes á la carte or opt for a family-style feast for $85 per person. Reservations are not required, but are highly encouraged.
Elf Spaghetti at Miss Ricky’s: This holiday season, Miss Ricky’s is bringing back the Candy-Filled Elf Spaghetti, inspired by the classic movie Elf. Executive Chef Mike Alaridi has reimagined this dish, combining crispy sweet spaghetti with Buddy’s favorite dessert toppings—M&M’s, chocolate syrup, raspberry sauce, marshmallows, vanilla ice cream, chocolate wafers, and a generous drizzle of maple syrup, available throughout the month of December.
Petterino’s has announced new drink specials and extended hours for the holiday season and the Christkindlmarket!
Holiday Cocktails at Petterino’s and Pasticceria: Starting Monday, Nov. 18, they'll be offering the following specialty drinks for both dine-in at Petterino’s and to-go at Petterino’s Pasticceria: Jesse’s House Made Nogg and Petterino’s House Made Hot Apple Cider. Hot Chocolate Selections include Original, Peppermint, Gingerbread and Vanilla Caramel. All hot chocolates will have the option to be spiked with alcohol for an extra $8!
Extended Hours: To better serve guests during the Christkindlmarket and Christmas festivities, extended hours for Petterino's starts November 18th. They'll be open on Monday until 9 p.m., Tuesday – Thursday until 10 p.m., Friday and Saturday until 11 p.m. and Sunday until 8 p.m. Petterino’s Pasticceria extended hours start Saturday, Nov. 23). Monday – Friday they will be open from 8 a.m. to 8 p.m. and on Saturday and Sunday from 11 a.m to 6 p.m.
Live Jazz Music at Petterino’s: Additionally, starting Monday, Nov. 18, they’ll be offering live jazz music every Monday at 6:30 p.m.
The Blackstone Hotel welcomes families to meet Santa Claus and the Grinch in the hotel's lobby on December 15. From 10 a.m. to noon, guests can capture holiday photos with the duo. After the photo opportunity, families are invited to Mercat a la Planxa for a special brunch. Children can enjoy complimentary cookies and hot chocolate, while adults indulge in festive cocktail specials. The regular brunch menu will be available, featuring Mercat's signature Spanish-inspired dishes made with fresh, local ingredients.
Fulton Market/West Loop
Punch Bowl Social welcomes The Ugly Christmas Sweater Shop for a limited-time holiday pop-up series. The pop-up will run Friday, Nov. 15, through Tuesday, Dec. 24 during Punch Bowl Social’s regular business hours, Sundays through Thursdays from 11 a.m. – 11 p.m., and Fridays and Saturdays from 11 a.m. – 1 a.m. Guests can peruse an assortment of upcycled and brand new holiday sweaters, ranging in price from $14.99 to $39.99, while sampling new seasonal craft cocktails and shareable dishes, as well as enjoying holiday décor and games including bowling, karaoke, dartsee, arcade games and more. The Ugly Christmas Sweater Shop was founded by Dallas-based vintage clothing guru Jeremy Turner in 2013 after he noticed a demand for the garments at his mobile thrift store. It took a multi-year hiatus during COVID and was relaunched at Punch Bowl Social Dallas in 2023. This year in addition to Dallas, it expands to Chicago and Austin for the first time.
In addition to the array of festive fashions, guests can enjoy the new menu of specialty craft cocktails, zero proof and punch, including To Me, You are Perfect, a fruit-forward punch served by the bowl or single cup; We Slept In!, a twist on the classic margarita; I Triple-Dog-Dare Ya, an old fashioned served with Ralphie glasses and a pickled filthy cherry and Son of a Nutcracker, an espresso martini also available in a N/A version, along with a variety of scratch-made eats. For those looking to host a private event this year, Punch Bowl Social can accommodate groups of all sizes in its versatile party spaces, while offering customizable menus of bites and libations.
The Italian Steakhouse from DineAmic Hospitality will open on Christmas Eve to serve a special tasting menu for $110 per person that brings a variety of offerings. Diners can add on a curated beverage pairing option for $49. Reservations are available on Christmas Eve from 4 p.m. - 9 p.m., Reservations can be found on their website.
La Serre will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
Bar La Rue will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
LYRA will be open for a la carte business on Christmas Eve, and reservations are now available on their website.
Gold Coast
The Pippin’s Lounge, a new piano bar tucked behind Pippin’s Tavern’s staircase transforms into a holiday-themed Tinsel & Tunes pop-up. Join Pippin’s Tavern every Friday and Saturday from 9pm to 1am for live dueling piano shows with a yuletide twist. Resident piano performers will play holiday tunes and Christmas carols to soak in the merriment all season long. With holiday decor, seasonal drinks and food, Pippin’s pianists will take audience requests with high-octane holiday singalongs.
Pippin's Tavern is also transforming into a winter wonderland this December! With festive decorations adorning the venue, the establishment invites all to revel in the holiday spirit. Guests can savor the season with specialty holiday cocktails, holiday beers on tap, and specials available in December. Guests are invited to stop in all season long for Happy Hour every Monday through Friday from 3pm to 6pm for $1.50 oysters, $6 draft beer, $6 draft wine, and BOGO small shares.
Located in the Magnificent Mile area, the hotel is offering several holiday offers and activations for locals and visitors alike.
Festive Holiday Dinner: Join Sofitel Chicago on Dec. 11 at 6 p.m. for its annual festive holiday dinner! With a focus on champagne pairings, the multi-course dinner is $99 per person and reservations can be made on Tock.
Festive Afternoon Tea: The hotel reimagined their tea service to help visitors and locals alike feel the festive spirit! Indulge in the tea service, but with a holiday twist. The new menu includes pastries and treats such as cranberry scones, Choux Puffs with Truffle Cream, Cranberry Scones, Eggnog Mousse and more! Make a reservation at Le Bar on Sofitel's website.
Winter Menu at Le Bar: In honor of the winter season, the hotel’s bar, Le Bar, rolled out several new cocktails inspired by it: McCalister Mule - bombay sapphire gin, koval cranberry liqueur, grenadine; Noel Royale - remy martin vsop, crème de cassis, faire la fete brut; Fireside Old Fashioned - maker’s mark, house bitters, spiced demera syrup, brown butter; PSL Season - bacardi spiced rum, pumpkin pie syrup, lemon juice, egg white; and Sweater Weather (Mocktail) - Seedlip Spice 94, spiced demerara, ginger beer, fresh lemon.
This holiday season, Four Seasons Hotel Chicago has partnered with Justice of the Pies for a Holiday Gift Shop & Pop-Up. From November 24 through December 25, guests can explore an exclusive selection of holiday pies, gift boxes, special merchandise, and more. Adorn Bar at Four Seasons will host a "Pies & Pours" experience, pairing signature Justice of the Pies treats with crafted cocktails by lead bartender Adam Chase. Guests can savor a slice of pie alongside a duo of hand-crafted cocktails (available for dinner only). Pairings include: Michigan Cherry Cheesecake paired with a Mezcal Last Word, Chocolate Espresso Cake paired with a Carajillo Espresso Martini and Blue Cheese Pear Praline Tart Tatin paired with a Spiced Cranberry French 75.
Guests can enjoy a slice and a sip duo for ($40), or indulge in the full experience for ($70), which also includes a signed cookbook. Additionally, from November 24 through December 25, these pies will be available on the Adorn Restaurant menu for a la carte ordering. In addition to the Pies & Pours experience, Adorn Restaurant will serve quiche options by Justice of the Pies for brunch. A curated collection of Justice of the Pies merchandise will be available for purchase in the hotel lobby.
Lakeview
Inspired by Chappell Roan’s “Pink Pony Club”, the Big Star crew is decking their halls with glittery hanging ornaments, a Christmas tree dressed up in pink cowboy hats, and a new lineup of food & drink specials. Look out for limited-time menu items including the Smokey Brisket Nachos ($18) with beef brisket, cheesy nacho sauce, salsa seca, pico de gallo, black beans, and guacamole and Cowboy Coffee ($12), a caffeine kick with a sweet finish featuring La Colombe Cold Brew, cinnamon honey, Buffalo Trace Cream, and bourbon, garnished with whipped vanilla cream, a candy cane, and sprinkles. The pop-up will expand on its normal catalog of cowboy classics with a heavy emphasis on Christmas tunes combined with modern country-infused classics— think Beyonce’s Cowboy Carter and Shaboozey. Classic holidays songs from Dolly Parton and Taylor Swift can also be expected.
Lincoln Park
River Shannon is celebrating the season with holiday decor, festive drinks, holiday beers on tap, and holiday-themed treats for all furry visitors. From the holiday menu, guests can choose from classic drinks with a holiday twist like the Claus-Mopolitan, Polar Paloma, Mistletoe Mule, Rudolph’s Old Fashioned and more. Known for its array of board games onsite, guests can also expect Holiday Game Nights at River Shannon, featuring holiday board games galore. Upcoming holiday-themed events:
Cookies & Cocoa: Every Monday in December from 4 p.m. to 6 p.m., guests can unleash their inner cookie artist during a festive afternoon of cookie decorating. River Shannon provides all the cookies, icing, and festive toppings needed to create edible masterpieces. Visitors can also purchase a boozy hot cocoa from the holiday drink menu and decorate with toppings from the Boozy Hot Cocoa Bar.
Dog Photos with Santa: Santa Claus is coming to River Shannon! Patrons can stop in with their furry friends on Sunday, December 1 and Sunday, December 15 from 12pm to 3pm for a complimentary photo opp with Santa.
Navy Pier
Margaritaville is inviting guests to its Holiday Pop-Up Bar from Friday, Nov. 15 to Sunday, Jan. 5. to enjoy holiday décor, drinks and activities. Margaritaville is transforming into a festive winter paradise, with holiday decorations and a seasonal ambiance. It is also putting an island twist on classic holiday flavors with five original drinks including Winter Wave and Deck the Palms, which will be served in limited-edition collectible ornament cups:
Sleigh Ride – A mix of Fireball Whiskey, Margaritaville Passionfruit Tequila, tart cranberry, and a splash of lemon with a hint of holiday spice.
Beachside Grinch – This concoction blends melon liqueur, Parrot Bay Coconut, and a festive kick of Fireball Whiskey. Topped with a cranberry float.
Kringle & Coke – Crème de menthe and crème de cocoa are matched with Parrot Bay Spiced Rum, lemon, and classic Coca-Cola.
Winter Wave – This blend of Basil Hayden bourbon and Grand Marnier is sweetened with coconut syrup and balanced by the tang of lime and cranberry juice.
Deck the Palms – With Espolon Blanco Tequila, a splash of Grand Marnier, and creamy Pina Colada mix, A splash of cranberry juice adds a touch of red.
Old Town
The Lodge Tavern is transforming into a holiday wonderland complete with twinkling lights, wreaths, garland, and more. From the holiday menu, guests can choose from festive riffs on classic cocktails like Mule-Tide Greetings, Ebenezer’s Old Fashioned, Mrs. Clausmo and more. And for those looking to warm their bellies, The Lodge Tavern will offer a hot cocktail menu featuring the Ho Ho Hot Toddy, Irish You A Merry Christmas, St. Nicks Cider, holiday beers on tap, and more.
Dog Photos with Santa: Santa Claus is coming to The Lodge Tavern! Patrons can stop in with their furry friend on Sunday, December 15 from 12pm to 3pm for a complimentary photo opp with Santa.
All December long, guests are invited to celebrate the season with games galore during Holiday Game Nights. She-nannigans will be decked out in decor and will feature holiday-themed board games, in addition to darts, pop-o-shot, pong, and giant Jenga. And, of course, no holiday gathering is complete without seasonal drinks. She-nannigans will feature a special holiday menu with seasonal twists on classic cocktails.
Every Thursday through Sunday starting at 5 p.m., She-nannigans DJ will be spinning festive tunes and party hits. Guests are also invited to take center stage every Thursday evening at She-nannigans for Holiday Carol-oke starting at 8pm. And on Friday, December 20 at 7pm, guests are invited to dust off their quirkiest holiday sweater and join She-nannigans for an Ugly Sweater Holiday Party!
River North
Three Dots and a Dash launches their River North Pole bar takeover beginning November 15. The team of the River North cocktail bar is transforming their space from the sandy beaches of a tropical paradise into a snowy winter wonderland escape all holiday season long. Complete with winter and holiday decorations throughout the space, a dedicated specialty holiday cocktail menu with both hot cocktails and themed sippers that also feature the same glassware and mugs as their traditional menu (even a speciality Snowman mug for all holiday mug collectors), Three Dots is a place to celebrate this time of year with friends, family and out of town visitors. Plus, the team’s retail program is available and open in the bar daily providing a one-stop-shop for holiday gift giving, particularly for those cocktail connoisseurs.
With the holiday season approaching, Nonnina offers an exclusive and interactive 5-course Chef’s Table Experience, for holiday dining with friends and family. During the experience, Executive Chef John Boudouvas crafts a customized 5-course tasting menu tailored to your preferences. He then guides you through each course, explaining the inspiration behind the dishes and the carefully selected premium wine pairings. The private dining space comfortably accommodates up to 10 guests, which makes it a setting for special occasions and celebrations. For reservations, guests can contact Brian Lachman at brian@nonninachicago.com or call 312-822-0077.
Sing along to your favorite carols at Redhead Piano Bar! The Redhead Piano Bar invites guests to sing along to all the holiday classics with nightly live piano music and performances from 7 p.m. to 4 a.m. The late night spot decked out with garland, lights, and mistletoe will feature a special limited time holiday cocktail menu including Candy Cane with Vanilla Vodka, Bailey’s, and Peppermint Schnapps, Jingle Juice with Bourbon, Cranberry Juice, and Ginger Ale, Kris Kringle Kir Royale with Cranberry Juice, Chambord, and Korbel, and more. Guests who purchase a holiday cocktail in December will receive a raffle ticket for the chance to join The Redhead’s piano player on stage. Each Monday through Thursday at 9 p.m., the piano player will draw a ticket and invite the lucky winner to sing a holiday carol or any song of their choice.
The Reindeer Games Christmas Pop-Up at Headquarters Beercade launches on Friday, November 22nd with all new Christmas decor and installations, Christmas-themed events, cocktails, and more! Immerse yourself in a holiday wonderland filled with lots of photo opps like a full-sized sleigh as you take a ride through the North Pole. Have a seat on the "Naughty or Nice" throne, and make lots of holiday memories with your crew.
Kinzie Chophouse will offer their annual Festive Odyssey tasting menu during the month of December. With eight courses, it's a celebration menu to enjoy over the holiday season with family and friends and offers steak and seafood courses. Kinzie Chophouse's Festive Odyssey tasting menu will be available Fri - Sun evenings throughout December and on Christmas Eve and New Year's Eve from 5 p.m. - 9 p.m. Priced at $150 per person, reservations can be made on their website.
Executive Chef Fabio Viviani’s full a la carte menu will be available at Siena Tavern, with the addition of three special holiday preparations this Christmas Eve: lamb cappelletti: pecorino, mint, celery root; berkshire pork loin: charred radicchio, smoked onion soubise, walnut and currant sofrito; and dark chocolate mousse white chocolate peppermint bark, pistachio praline. Reservations are now available on their website.
Brindille will be open for Christmas Eve from 4–8 PM where guests can experience "The Winter Réveillon", inspired by the French tradition of Le Réveillon—a celebratory dinner enjoyed on Christmas and New Year’s Eve. The name comes from the French word for "awakening," as these dinners are meant to be savored late into the night. For this special occasion, they're offering both à la carte selections and a prix fixe menu. Reservations can be made on Resy.
On Christmas Eve, Dec. 24, the Godfrey Hotel Chicago will host a festive brunch with Santa from 11 a.m. to 4 p.m. The brunch buffet will feature breakfast classics, a carving station with prime rib, and sweet offerings — like pancakes and French toast, plus, an avocado toast bar, an acai bowl station, and more. The dessert selections will include Christmas cookies, Santa cake pops, peppermint bark, and hot cocoa. Priced at $49 per adult and $15 for children under 12. Reservations can be made on Tock.
Hard Rock Cafe Chicago invites families to celebrate the holiday season with Breakfast with Santa on Dec. 24, from 11 a.m. to 1 p.m. Guests can enjoy a festive breakfast buffet while meeting Santa Claus and photo opportunities. Tickets are $25 for adults and $13 for children, available on Eventbrite.
Ukrainian Village
Treat yourself to Heritage's Christmas Eve tradition with the Feast of the Seven Fishes tasting. The dinner is 5 courses and includes Smoked Oyster and Cauliflower Tart with Osetra Caviar; Sliced Sashimi of Tuna and Hamachi with Coconut Dashi, Grand Cru Caviar, Cilantro Oil, Crispy Shallots; Steamed Mussels with Apple Cider, Kimchi Polish Sausage and Sourdough; Grill Roasted Red Snapper with Braised Collard Greens and Pimento Grits; and Swordfish au Poivre with Truffle Mash, Bordelaise and Onion Rings. The Feast of the Seven Fishes tasting is $200 per person, with an optional beverage pairing available. Reservations can be made on Tock.
Heritage Restaurant & Caviar Bar also honors Hanukkah again this year with their a la carte take home menu. Heritage's homemade options include: Smoked brisket, smoked & cured fish (including their famous gravlax and pickled herring), latkes, matzo ball soup, and many other Hanukkah-friendly house specialties. Pickup is available Dec 24th through Jan 1st. Pre-orders accepted by phone at 773-661-9577, in-person, and online beginning in early December.
Multiple Locations
The Goddess and Grocer has catering options for Hanukkah and Christmas this year. The menus offer options for those in need of vegetarian, vegan, gluten-free, and dairy-free options that can be pre-ordered + select items in stores.
The Goddess and Grocer Christmas: For holiday gatherings of any size, The Goddess and Grocer’s Christmas catering menu options include Christmas Dinner for Two $85, Family Matters (serves 6) $225, Ham It Up (serves 6) $225, Vegan Dinner for 2 $85 and a la carte food, wine, and more. The menu also offers options for those in need of vegetarian, vegan, gluten-free, and dairy-free options! The Christmas catering can be ordered at https://www.goddessandgrocer.com. Delivery is available and FREE pickup is available at all locations. Select items from the Christmas menu will be available in stores.
The Goddess and Grocer HANUKKAH: The Goddess and Grocer will offer an a la carte to-go / delivery menu full of twists on the classics with vegetarian, vegan and gluten-free options as well as Sommelier wine selections. To order, please visit GoddessandGrocer.com. Select items will be available in stores for pick up as well. Locations include Fulton Market, River North, Gold Coast, and Bucktown.
Bar Siena in the West Loop and Skokie will be open on Christmas Eve, serving their regular menu and is accepting dinner reservations through 7:45 p.m.
Enjoy Q-BBQ's seasonal Prime Rib Slices served with Alabama White Sauce and Au Jus, or the Smoked Mashed Potatoes served with Brisket Gravy - for a limited time only! Available Friday through Sunday only from December 6th through December 27th. Online ordering to come.
Christmas Catering for Pick Up Offerings include Slices of Prime Rib; Alabama White Sauce and Au Jus; Whole or Half Prime Rib; Alabama White Sauce and Au Jus; Smoked Mashed Potatoes; and Brisket Gravy. Available to order from Monday, December 6th through December 18th. Online ordering link to come. Pick Up: Monday, December 23rd and Tuesday, December 24th.
Suburbs
VIOLI will be open for a la carte business on Christmas Eve, and reservations are now available on their website.
The newly-opened Cooper's Hawk Schererville invites everyone this Christmas Eve to experience its winery, restaurant, and Napa-style tasting room concept to more guests in the region. Led by a culinary team with Executive Chef Matt McMillin and local culinary leader Nick Gard, guests can enjoy a contemporary-American menu infused with international flavors and wine pairings. Open from 11 a.m. to 9 p.m., the restaurant also features a special Wine O'Clock Happy Hour from 3 to 5 p.m., offering five appetizers and wines by the glass. Reservations can be made online.
Fat Rosie’s opened its newest location in Rosemont in October and has other restaurants throughout the Chicagoland area in Naperville, Schaumburg, Frankfort, Lincolnshire, and Lincolnwood. The team will be hosting its annual Brunch with Santa at all six locations. In addition to holiday music and an appearance from Santa, the team will be offering one complimentary photo per guest, with the option to purchase a larger photo and frame.
Brunch with Santa Schedule: On Sunday, December 1, Santa will be at the Schaumburg and Rosemont locations from 11:00 AM to 3:00 PM. Then on Sunday, December 8, Santa will show at the Lincolnwood and Lincolnshire locations from 11:00 AM to 3:00 PM. Finally, on Sunday, December 15, Santa will be at the Naperville and Frankfort locations from 11:00 AM to 3:00 PM
Other holiday specials include Fat Rosie's Mistletoe Margarita ($15) featuring Casamigos Reposado Cristalino, Peach Liqueur, Cranberry Juice, Citrus, Fresh Cinnamon-Spiced Cranberries, and a Sugar-Tajin rim. Available for the month of December. There will also be a Seasonal menu available until January 5 (not available at Rosemont location).
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