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Mordecai 

Mordecai Chicago (3632 N. Clark St) is a bi-level cocktail bar that offers a collection of vintage spirits and crafted cocktails. Such as sipping Mordecai’s $15 Bleacher Tea, a fizzy cocktail designed for memory association with baseball, or the $15 Bills in Foil, where tequila, agave, and pear cider are complemented by a salted rim and garnished with lime.

Tanta 

Readers can celebrate their holiday weekend in the hills of Peru with Tanta Chicago’s (118 W. Grand) $14 Classic Pisco Sour where pisco, lime, simple syrup, egg white, and bitters come together to create a cocktail. Tanta also offers a $14 Prickly Pear Margarita. Tequila is mixed with a juicy prickly pear puree and combined with agave. Served with a citrus salt rim and a lime.

Frontier

What’s Labor Day weekend without a margarita? Readers can select one of Frontier Chicago’s (1072 N. Milwaukee Ave) many margarita blends, such as their $12 Pineapple Jalapeno Margarita ($44 for pitcher). Here, Tanteo Jalapeno Tequila, pineapple juice, lime, and spicy rum are blended together to create a slightly sour, yet juicy drink. Other margarita options include their $12 Tanteo Chipotle Margarita ($44 for pitcher) or $12 Mean Green Coconut “Melon-Rita”. 

Ina Mae Tavern

Bring the kids and dogs to Ina Mae Tavern (1415 N. Wood St) where the children can create their own Sno-Balls while the adults select in one of Ina Mae’s NOLA-inspired cocktails, such as their $12 Hurricane. For Ina Mae’s dog-friendly patio opt for their boozy frozen slushies that include $12 Pina Coladas, $12 Cucumber Mint Mojitos, and more.

The X Pot Chicago 

The X Pot Chicago (1147 S. Delano Ct East) offers a list of wagyu options that complement their cocktail selections with robotic servers available to lend a hand. With the option to dine in their dining room or bask in the summer air on their patio, guests can sip on cocktails ranging from their $14 Old Fashion built with Smoke Wagon Bourbon, simple syrup, and barrel aged bitters, to their $14 Once Upon A Time Creation that mixes together Roku Gin, yuzu lemon juice, cranberry juice, lychee syrup, and rose water.

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Photo courtesy of Ina Mae Tavern

aliveOne

After the barbecues, patrons can head to aliveOne on Monday, September 5 at 5 p.m. for Labor Day specials like $8 Copernicus cocktails (regularly $11) with Crown Royal, Pimms, simple syrup, lemon juice and ginger beer. At 8 p.m., guests will enjoy free music trivia from Whaddayaknow and free pool all night.

Central Park Bar

Chicagoans can keep the Labor Day weekend party going and join Central Park Bar on Monday, September 5 beginning at 8 p.m. Guests can select $8.50 beer and shot combos in the 3,500 square foot, dog-friendly Backyard Bar complete with covered outdoor bar, bumper pool table, picnic tables, porch swings and fire pit. 

Cody's Public House

Always dog-friendly inside and out, Cody’s Public House in West Lakeview will open early at 1 p.m. on Monday, September 5 for Labor Day. Guests are invited to “Bring Your Own Meat” (BYOM) and use the grill in Cody’s beer garden to grill up all their Labor Day favorites. Cody’s beer garden also features TVs, darts and bean bags. 

Easy Bar

Easy Bar will open at  5 p.m. on Monday, September 5 for a Labor Day Half-Price Happy Hour from 5 p.m. to 7 p.m. Other all day specials will include $4 Goose Island, and $8 beer and shot combos. 

Estelle's

Estelle’s will open at 10 p.m. on Monday, September 5. Guests can select a late-night barbecue with half-price BYO (build-your-own) burgers all evening. 

Matcha Cita

Matcha Cita in the West Loop will offer festive specials on Monday, September 5 like a Red, White and Bluetiful matcha drink with vanilla almond milk, collagen, blueberry, and beet powder for $8.95, a Funfetti Waffle with strawberries, banana, whipped cream and red, white and blue sprinkles for $9.95 and Matcha Cita’s signature Blue Bowl blended with blue spirulina, banana, mango and almond milk for $13.95. 

Remedy

Remedy will open on Labor Day at 4 p.m. and guests can choose drinks with half-price happy hour from 4 p.m. to 7 p.m. For end of summer vibes, Remedy offers cocktail selections for $12 each like the El Diablo with Olmeca Altos or El Buho Mezcal, Creme de Cassis, lime juice, and ginger beer, or the Bug Juice with Sweet Gwendoline Gin, Green Chartreuse, lime juice, and fresh cucumber.

Rewired Pizza Bar and Cafe

Rewired Pizza Cafe & Bar in Edgewater, will be open throughout Labor Day weekend and offers a 40 seat dog-friendly patio. Guests can kick off the weekend early on Thursday, September 1 with Rewired’s Date Night special ($49 three-course meal for two and a bottle of wine) paired with live music from 6 p.m. to 9 p.m. 

Rewired will also offer happy hour specials on Thursday, September 1; Friday, September 2; and Monday, September 5 from 3 p.m. to 5 p.m. featuring $3 slices, half-off select apps, $4 house wine (malbec, chardonnay, rosé), $5 drafts, and a beer, shot, slice combo for $10. 

Sweet Mandy B's

Sweet Mandy B’s in Lincoln Park and Streeterville will be open until 4 p.m. on Labor Day, Monday, September 5. Guests can choose sweet treats like Sweet Mandy B’s Just Dough It for $5.50. Sweet Mandy B’s will bring it back for the month of September. Just Dough It will be available daily at the Streeterville location and on Saturdays and Sundays only in Lincoln Park. Just Dough It features eggless chocolate chip cookie dough sandwiched between two chocolate chip cookies. 

Sweet Mandy B’s Lincoln Park location will also feature festive back-to-school themed cut out cookies. The cookies start at $3.60 each and are available now through the end of September. 

The Owl

Guests looking for a late-night Labor Day party can head to The Owl in Logan Square for The Owl’s new Monday night Psychedelic Disco Punk Dance Party that runs from midnight until 4 a.m. Party-goers can cool off with $6 Margaritas all night long.

The Rambler Kitchen + Tap

Fans of ABC’s The Bachelorette can watch the “Fantasy Suite” episodes at The Rambler on Labor Day at 7 p.m. during their weekly viewing party. The bar will broadcast the show with audio while guests participate in bingo for prizes as they watch the drama unfold. Themed “double trouble” drink specials include the Rachel’s Rum Sunset with RumHaven Coconut, pineapple, orange juice and grenadine ($9), the Split Spritz with Fragola Wild Strawberry Liqueur, Mionetto Prosecco, club soda and strawberry ($9), a Fantasy Suite Martini with Mozart White Chocolate Strawberry Cream, Deep Eddy Vodka, White Creme de Cacao, cream, strawberry ($9) and more. For guests looking for a late night snack, The Rambler’s full menu is now available Sunday through Friday until 12 a.m. and Saturday until 1 a.m.

Uvae Kitchen and Wine Bar

For Chicagoans staying in town this Labor Day weekend, Uvae Kitchen and Wine Bar in Andersonville is hosting a Rosé All Day wine tasting on Saturday, September 3 at 3 p.m. on the patio as an end of summer send off. The $35 per person tasting features 4 four-ounce pours and will be led by Uvae Sommeliers and guest wine makers. Small bite add-ons include a Cheese Plate ($15), Cheese & Charcuterie Plate ($20) and Duck Pâté ($12).

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Photo courtesy of Rewired Pizza Bar and Cafe

The Forester Hotel and Oaken Bistro + Bar

The Forester Hotel (200 N Field Dr) is offering a picnic package, an al fresco dining experience that features a picnic basket, foldable fleece travel blanket, a bottle of wine, 2 glasses, a corkscrew, and customized personal requests that can be made to the Executive Chef of the hotel’s on-site restaurant, Oaken Bistro + Bar. Continue the weekend at Oaken and choose from a variety of crafted cocktails and spirits including The Oak Tree, featuring Charred Oak Rye, Airloom Alchermes Liqueur, Grapefruit Infused Simple, Lemon juice, Sfumato Rabarbaro Amaro, and Bittercube Jamaica No.2 Bitters ($16), to a Dulce Vida Organic Margarita featuring 100% Puro Agave Tequila, Agave Nectar, and Fresh Lemon and Lime Juice ($14).

Depot 226 and the Canopy Central Café

The newly opened boutique-style hotel, the Canopy by Hilton Chicago Central Loop (226 W Jackson Blvd.) is offering all new menus from the hotel’s on-site restaurant activations Depot 226 and the Canopy Central Café. Select from a fresh Italian Capo with Roast Beef, Italian Jus, Giardiniera, Purgatory Sauce, and Smoked Provolone on French baguette ($13), or sweets including homemade brownies ($6), eclairs ($5), and chocolate fudge cake ($8). Covered self-parking is additionally available for $22 dollars nightly with in and out privileges to eat on the go.

Game of Irons

This Labor Day weekend, swing over to golf simulator facility Game of Irons, 3041 Butterfield Rd Suite 104, as the facility offers a variety of menu offerings from it’s on-site “Seven Iron Bar” including a Pineapple Bliss Plantation featuring 3-star Rum, Pineapple Juice, Simple Syrup, and Lime Juice ($11), The Bee's Knees featuring Citadelle Gin, Honey Syrup, and Lemon Juice ($12), or a John Daly Long Island featuring Mile High Vodka, Mile High Denver Dry Gin, Plantation Rum, Thatcher's Elderflower Liqueur, Lemon Juice, and Iced Tea. 

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