This year’s Labor Day celebrations include extended brunches, patio parties, drink specials, mini golf, boat rentals, college football watch parties and family-friendly dining offers throughout Chicago and the suburbs.
Whether you want to spend the unofficial final weekend of summer on the water, enjoy brunch with friends or find a late-night Labor Day party, here are some of the best things to do in Chicago for Labor Day weekend and throughout September 2026.
aliveOne
aliveOne will close out Labor Day weekend with free music trivia, drink specials and complimentary pool. The Lincoln Park bar opens at 8 p.m. on Monday, September 7, with $7 Old Style and whiskey-shot combinations, $1 off domestic beers and music trivia hosted by Whaddayaknow Trivia. Guests can play pool for free after trivia.
Location: 2683 N. Halsted St., Chicago
Carmine’s
Carmine’s on Rush Street is extending summer with The Last Spritz of Summer on Monday, September 7. From opening until 4 p.m., guests can relax on the restaurant’s second-floor patio overlooking Rush Street and order $12 Aperol Spritzes, Hugo Spritzes and Lemon Ice cocktails.
The one-day celebration offers a final opportunity to enjoy an Italian-inspired summer lunch or afternoon cocktail in the Gold Coast.
Casa Chi by Chef Richard Sandoval
Casa Chi offers Japanese-Peruvian Nikkei cuisine, sushi, cocktails and inventive small plates along the Magnificent Mile. Its happy hour runs from 4 to 7 p.m. and features specialty cocktails, bubbles, wine and shareable dishes.
Beginning at 7 p.m., the restaurant’s $35 Girl Dinner includes a seasonal margarita or Champagne, swordfish dip or guacamole, and a three-piece omakase selection. Walk-ins are welcome, and reservations are available through OpenTable.
Central Park Bar
Central Park Bar will celebrate Labor Day on Monday, September 7, with half-price drinks, free bingo and one of Avondale’s largest patios.
The bar opens at 4 p.m., with half-price drinks excluding shots available until 7 p.m. Free bingo follows from 7 to 10 p.m. Weather permitting, festivities will take place in the 3,500-square-foot Backyard Bar, which includes a covered bar, picnic tables, porch swings, bumper pool, a photo booth, a claw machine and a fire pit.
Location: 2924 N. Central Park Ave., Chicago
Chicago Boat Company
Chicago Boat Company offers customizable, self-captained boat rentals for spending Labor Day weekend on the Chicago River or lakefront.
Its fleet includes playful Donut Boats, luxury Duffy boats and colorful retro boats, with docks located from Avondale to downtown Chicago. Guests can bring their own food and beverages aboard most boats, while food and beverage packages are available for yacht charters.
Options range from peaceful cruises along tree-lined sections of the river to downtown sightseeing and skyline views from the lakefront.
Chicago Boat Rentals
Chicago Boat Rentals offers private pontoon boats and yacht rentals for families, groups of friends, corporate outings and end-of-summer celebrations.
Guests can drive the gas-powered pontoon boats themselves after receiving instructions from the team, with no boating license required. Rentals offer Chicago skyline views, BYOB access and customizable additions such as decorations, charcuterie boards and Champagne.
First-time guests can receive $50 off a pontoon rental or $150 off a yacht rental with promotional code SOCIALITE2026.
Cody’s Public House
Cody’s Public House is kicking off college football season with Labor Day weekend watch parties on Saturday, September 5 and Sunday, September 6.
The West Lakeview bar opens at 11 a.m. Saturday for ESPN College GameDay’s featured matchup, shown with full game sound. Specials include $5 mimosas, $6 22-ounce Miller Lite cups, $7 Walk of Shame Bombs and $30 Surfside buckets.
Location: 1658 W. Barry Ave., Chicago
DineAmic Hospitality Restaurants
DineAmic Hospitality will offer Labor Day brunches, cocktails and holiday dining at several Chicago restaurants:
- Bandit: Monday brunch
- Bar La Rue: Monday brunch
- Bar Siena in the West Loop: Monday brunch
- LYRA: Early Sunday opening and all-day happy hour
- NAIA: Labor Day lunch
- Siena Tavern: Monday brunch
Hours and reservations vary by restaurant.
Easy Bar
Easy Bar will open at 4 p.m. on Monday, September 7, with a half-price happy hour from 4 to 6 p.m.
Labor Day drink specials include $4 Montucky Cold Snacks, $5 Espolòn Blanco shots, $5 Underbergs and $5.50 domestic bottles and cans. Weather permitting, guests may also relax on the Wicker Park bar’s dog-friendly sidewalk patio.
Location: 1944 W. Division St., Chicago
Estelle’s
Estelle’s will hold its annual late-night Labor Day gathering beginning at 10 p.m. on Monday, September 7. Guests can receive half-price build-your-own burgers with the purchase of a drink.
Location: 2013 W. North Ave., Chicago
Farm Bar
Farm Bar will serve locally sourced, Midwestern-inspired food throughout Labor Day weekend at its Lakeview and Ravenswood restaurants.
Guests can visit for weekend brunch or dinner featuring seasonal ingredients from the restaurant’s Brown Dog Farm and handcrafted cocktails. Walk-ins are welcome, with reservations available through OpenTable for Farm Bar Lakeview and Farm Bar Ravenswood.
Fogo de Chão
Fogo de Chão is offering a family-friendly Labor Day dining special. Children under age 12 can receive a complimentary children’s churrasco with the purchase of an adult churrasco.
Restrictions may apply, so families should confirm the offer with their preferred location before visiting.
The Graystone Tavern
The Graystone Tavern is kicking off Labor Day weekend with college football watch parties on Saturday, September 5 and Sunday, September 6.
The Wrigleyville tavern will show the Kansas State Wildcats game at 6 p.m. Saturday and the Washington Huskies game at 3 p.m. Sunday on 15 televisions throughout the bar and weatherproof patio. Guests can also enjoy team-inspired food and drink specials.
Washington specials include a $6 Seattle Dog, $6 Elysian Space Dust, $6 Husky Bombs, $6 Washington Apple shots, $20 Coors buckets and $30 Surfside buckets. Kansas State specials include a $12 Mac and Cheese Grilled Cheese, $5 Nancys, $6 Wildcat Bombs, $8 Belfast Bombs and $30 Super Lyte buckets.
Location: 3441 N. Sheffield Ave., Chicago
The Grillroom Chophouse & Wine Bar
The Grillroom Chophouse & Wine Bar will start Labor Day weekend with an extended kickoff happy hour from 4 to 6 p.m. on Friday, September 4 and Saturday, September 5.
Specials include $10 select wines and house margaritas, $12 barrel-aged Old Fashioneds, oysters, meatballs, Tuscan toast and filet skewers. Guests can also order the $69 Summer Grill Board, featuring sliced steak, grilled shrimp, asparagus, corn, chimichurri and garlic butter.
The Smoke Show cocktail is available for $12 and combines reposado tequila, mezcal, pineapple juice, lime juice and agave. The downtown restaurant’s patio overlooks Monroe Street.
Location: 33 W. Monroe St., Chicago
The Hampton Social
The Hampton Social will extend its bottomless brunch across Labor Day weekend from Saturday, September 5 through Monday, September 7. Brunch will be available from opening until 3 p.m.
Availability and opening times may vary by location, so reservations are recommended.
Kindling
Kindling offers live-fire cooking, seasonal dishes, seafood, steaks and craft cocktails in downtown Chicago.
The restaurant will be open for lunch and dinner during Labor Day weekend, with outdoor patio seating available for guests hoping to enjoy the final days of summer. Walk-ins are welcome, and reservations are available through OpenTable.
Old Town Pour House
Old Town Pour House will extend its weekend brunch through Labor Day and open one hour earlier at 10 a.m. Brunch will be served from 10 a.m. to 3 p.m. on Saturday, September 5, Sunday, September 6 and Monday, September 7.
The menu includes Stuffed French Toast, Avocado Toast, Chilaquiles, Chicken and Waffles, a Breakfast Burger, Brisket Biscuits and Gravy, and Steak and Eggs. Children’s selections, mocktails, cocktails, mimosa flights and breakfast shots will also be available.
The extended brunch is offered at the Oak Brook and Naperville locations.
The Owl
The Owl will host a late-night Labor Day party from 10 p.m. Monday, September 7 until 4 a.m. Tuesday.
The Logan Square bar will offer $10 cocktails throughout the night, including the Smokey Kiss with mezcal, Cynar and sweet vermouth, and the Tipsy Rose with strawberry aperitif, rhubarb amaro, bubbles and sparkling rosé.
Location: 2521 N. Milwaukee Ave., Chicago
Puttshack
Puttshack is offering several ways to play, dine and save during Labor Day weekend and throughout September.
From September 4 through 7, guests can use promotional code LDW25 to receive 25% off tech-infused mini golf. The promotion is available at all Puttshack locations, including Oak Brook and Skokie.
Additional September offers include:
- World Mini Golf Day: Guests who play on September 21 will receive a bounce-back card for one complimentary game, redeemable through October 21.
- $9 After 9: On Saturday nights, use code 9AFTER9 for nine holes of mini golf for $9, with select $9 mixed drinks and shareable dishes.
- Happy Hour: Available Monday through Friday from 3 to 6 p.m., with $1 wings, $3 draft beers, $5 white queso and chips, $10 cocktails and a $10 Signature Skirted Double Cheeseburger.
- All You Can Putt: Unlimited mini golf is available Sunday through Friday.
- Dirty Sodas: Peaches and Cream, Island Creamsicle, Strawberry Fields and Milk Bar Cookie Monster flavors are now available.
Remedy
Remedy will hold a late-night Labor Day party from 10 p.m. Monday, September 7 until 4 a.m. Tuesday.
Guests can receive a complimentary hot dog, while supplies last, with the purchase of a $5 Malört shot.
Location: 1910 N. Milwaukee Ave., Chicago
Sifr
Sifr offers a Michelin Bib Gourmand-recognized Middle Eastern dining experience featuring wood-fired flavors from Chef Sahil Sethi.
For Labor Day weekend, guests can select the $60 chef’s tasting menu or order mezze, hearth-roasted specialties and shareable dishes à la carte. Walk-ins are welcome, and reservations are available through SevenRooms.
The Smith
The Smith in River North will serve Labor Day weekend brunch dishes including Vanilla Bean French Toast, Shrimp and Grits, and Potato Waffle Benedicts.
Its weekday Martini Hour is available at the bar from 3 to 6 p.m. and features $12 martinis, oysters and bar bites. Martini selections include the Caprese, Dirty Blue Olive, Pickle Rick and Espresso Martini. Walk-ins are welcome, and reservations are available through OpenTable.
Sunda New Asian
Sunda New Asian will offer Labor Day weekend dining at its River North and Fulton Market restaurants.
At Sunda River North, guests can dine on the spacious patio, enjoy East Meets West weekend brunch or stop in for Monday happy hour from 4 to 6 p.m. Happy hour selections include cocktails starting at $10, $8 sake, wine and beer, and $8 bar bites and handrolls.
Sweet Mandy B’s
Sweet Mandy B’s will offer Labor Day treats from Friday, September 4 through Monday, September 7.
The bakery’s holiday specials include six-packs with three yellow cupcakes and three chocolate cupcakes decorated with red, white and blue star-shaped sugar. Both the Lincoln Park and Streeterville shops will be open from 9 a.m. to 4 p.m. on Labor Day.
Locations: 1208 W. Webster Ave. and 254 E. Ontario St., Chicago
Sweetwater Tavern & Grille
Sweetwater Tavern & Grille will extend its weekend brunch through Labor Day and open one hour earlier at 10 a.m. Brunch will be served until 3 p.m.
Selections include Stuffed French Toast, Avocado Toast, Chilaquiles, Chicken and Waffles, a Breakfast Burger, Brisket Biscuits and Gravy, and Steak and Eggs. Children can choose from breakfast tacos, pancakes and French toast sticks. Cocktails, mocktails, mimosa flights and breakfast shots will also be available.
Location: 225 N. Michigan Ave., Chicago
Tune-Up
Tune-Up will open at 4 p.m. on Monday, September 7, with half-price happy hour until 7 p.m.
Guests can enjoy the Avondale bar’s spacious patio and seasonal cocktails, including the Frozen Patio Paloma, ErotiColada and Dead Beat Beet. Patio availability is weather permitting.
Location: 3810 W. Belmont Ave., Chicago
Hours, prices, promotions and availability may change. Contact each business or make reservations in advance before visiting.
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