Labor Day weekend can be bittersweet. On one hand, it brings the unofficial end of summer. School is back in session, the days are getting shorter, and the weather will soon be getting colder. On the other hand, Labor Day means a long weekend holiday weekend, football season is around the corner, and maybe we're okay with the temperatures not hitting 90 degrees.
We've gathered up some of our favorite festivities happening all weekend long. Whether you're sad to see summer go or if you can't wait for the cool, crisp autumn air, there's something for everyone in Chicago this Labor Day weekend.
All events take place Monday, September 7th unless otherwise noted.
End Summer on the Patio with FREE Bingo at Central Park Bar
Celebrate the long weekend with a relaxed Labor Day happy hour at Central Park Bar (2924 N Central Park Ave) . Opening at 4 p.m., come enjoy half-price drinks (excluding shots) from 4 to 7 p.m. while soaking up the holiday on one of the area's largest patios. At 7 p.m. enjoy a few rounds of FREE Bingo until 10 p.m.
Weather permitting, the Labor Day festivities will take place in the 3,500-square-foot Backyard Bar, featuring a covered outdoor bar, bumper pool, picnic tables, porch swings, a photo booth, a claw machine, and a cozy fire pit. Whether you're gathering with friends or simply looking to make the most of the final days of summer, Central Park Bar offers the perfect setting to relax, sip, and celebrate.
Labor Day Patio Hangs at Tune-Up
Come make the most of Labor Day weekend at Tune-Up (3810 W Belmont) where you can soak up the final unofficial weekend of summer on the spacious outdoor patio. Arrive early and enjoy Tune-Up's signature half-price happy hour from 4 p.m. to 7 p.m. featuring seasonal specials like the Frozen Patio Paloma with Astral tequila, St. Germain, Squirt, grapefruit juice & lime juice and 'Tune it up' by adding Ghost habanero tequila floater on top. Other seasonal libations include the ErotiColada with Bacardi, Green Chartreuse, pineapple, lime juice, Dead Beat Beet with Los Vecinos mezcal, Giffard Ginger of the Indies, Supasawa, lemon juice, beet syrup, celery bitters and more.
Tune-Up's expansive patio offers the perfect setting to enjoy the long holiday weekend. With plenty of seating, refreshing cocktails, cold beer, and a welcoming neighborhood atmosphere, it's an ideal destination for celebrating the holiday.
Late-Night Labor Day Party at The Owl
For a late-night Labor Day party, head to The Owl (2521 N Milwaukee Ave) from 10 p.m. until 4 a.m. Sip on cocktails for only $10 each all evening like the Smokey Kiss with Union mezcal, Cynar, sweet vermouth, the Tipsy Rose with Dolin strawberry aperitif, Sfumato rhubarb amaro, bubbles, sparkling rosé and more.
aliveOne Closes Out Labor Day Weekend with Music Trivia and Drink Specials
After a day of Labor Day celebrations, aliveOne (2683 N Halsted St) is keeping the holiday weekend going with an evening of free music trivia, drink specials, and free pool. The bar opens at 8 p.m., offering $7 Old Style and whiskey shot combos, $1 off domestic beers, and music trivia hosted by Whaddayaknow Trivia. Following trivia, stick around for complimentary pool throughout the rest of the evening.
Labor Day Party with Free Hot Dogs and Drink Specials at Remedy
Remedy (1910 N Milwaukee Ave) is celebrating Labor Day with a late-night party featuring drink specials and a complimentary hot dog special. Open from 10 p.m. to 4 a.m., Remedy is offering a free hot dog (while supplies last) with the purchase of a $5 Malört shot.
Easy Bar Celebrates Labor Day with Half-Price Happy Hour and Drink Specials
Easy Bar (1944 W Division St), opening at 4 p.m., is celebrating Labor Day with half-price happy hour from 4 p.m. to 6 p.m. Come enjoy evening-long drink specials including $4 Montucky Cold Snacks, $5 Espolón Blanco Shots, $5 Underbergs and $5.50 Domestic bottles and cans.
Weather permitting, relax on Easy Bar's intimate, dog-friendly sidewalk patio, offering seating for 15 to 20 guests and a laid-back neighborhood atmosphere.
Estelle's Offers Late-Night Labor Day Burger Special
Estelle's (2013 W North Ave) is giving late-night diners another way to celebrate Labor Day with a special burger. Beginning at 10 p.m., enjoy half-price build-your-own burgers with the purchase of a drink. The late-night special is available during Estelle's annual Labor Day post-barbecue hangs, making it an ideal stop for those looking to grab a bite after holiday festivities.
Labor Day College Football Kickoff and Watch Party at Cody's
Cody's Public House (1658 West Barry Ave) is inviting college football fans to kick off college football season and Labor Day with a weekend full of games beginning Saturday, September 5. Cody's is opening at 11 a.m. on Saturday for the ESPN College GameDay featured matchup with full game sound. Enjoy game day specials including $5 Mimosas, $6 22-ounce Miller Lite cups, $7 Walk of Shame Bombs and $30 Surfside Buckets.
Labor Day Weekend College Football Watch Party at The Graystone Tavern
College football fans can kick off Labor Day weekend at The Graystone Tavern (3441 N Sheffield Ave) with wall-to-wall game day action, food and drink specials, and a lively atmosphere for two matchups including the Kansas State Wildcats on Saturday, September 5 at 6 p.m. and Washington Huskies on Sunday, September 6 at 3 p.m.
Enjoy team-inspired food and drink specials throughout the weekend. Washington Huskies Specials include $6 Seattle Dog, $6 Elysian Space Dust, $6 Husky Bombs, $6 Washington Apple shots, $20 Coors Light & Coors Banquet buckets and$30 Surfside buckets. Kansas State Wildcats Specials are $12 Mac & Cheese Grilled Cheese, $5 Nancy (Old Style & pineapple juice), $6 Wildcat Bomb, $8 Belfast Bomb, $30 Super Lyte buckets
Graystone is airing both games across 15 TVs throughout the bar and weatherproofed patio, complete with overhead string lights, and classic outdoor games including bags, giant Jenga, and giant Connect 4.
Kick Off Labor Day Early with Pre-Labor Day Happy Hour at The Grillroom
Get a head start on Labor Day weekend at The Grillroom Chophouse & Wine Bar ( 33 W Monroe St) with a special Pre-Labor Day Happy Hour on Friday, September 4 and Saturday, September 5 from 4 p.m. to 6 p.m. Before the holiday crowds arrive, unwind on The Grillroom's patio overlooking vibrant Monroe Street while enjoying signature cocktails, wines, and shareable bites in the heart of downtown Chicago.
Happy Hour specials include $10 select wines and House Margaritas, $12 Barrel-Aged Old Fashioneds, and a variety of crowd-pleasing small plates, including East Coast Oysters, Meatballs, Tuscan Toast, and Filet Skewers. With front-row views of the city's energy, The Grillroom offers the perfect setting to ease into the long weekend.
For those looking for a more substantial meal, enjoy The Grillroom's Summer Grill Board ($69), designed for sharing or as a satisfying entrée. The board features sliced steak, grilled shrimp, grilled asparagus, corn on the cob, house-made chimichurri, and garlic butter, bringing together the flavors of summer.
Pair the Grill Board with The Smoke Show ($12), a smoky-sweet cocktail made with Reposado Tequila, Mezcal, pineapple juice, fresh lime juice, and agave, finished with a charred pineapple garnish for the perfect holiday weekend toast.
Celebrate Labor Day Weekend with Sweet Treats from Sweet Mandy B's
Just in time for backyard barbecues and long weekend gatherings, Sweet Mandy B's Lincoln Park (1208 W. Webster Ave) and Streeterville (254 E. Ontario St.), is dishing out holiday specials starting Friday, September 4, and will remain open on Labor Day, Monday, September 7, from 9 a.m. to 4 p.m. Specials include patriotic 6-packs of Sweet Mandy B's beloved cupcakes (three classic yellow and three rich chocolate) topped with whimsical red, white, and blue star sugars. It's the perfect crowd-pleasing dessert to bring to any celebration.
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