Labor Day is just around the corner and there's no better place to celebrate than Chicago, the birthplace of the holiday! With so much to do in the Windy City, there’s no need to travel elsewhere to round out the summer. Here’s where to celebrate this Labor Day weekend:
Brunch Specials
Cindy's Labor Day Brunch
Take in sweeping views of the Lakefront from Cindy's Rooftop this Labor Day. Cindy's is serving up its signature Labor Day Brunch, with menu highlights including Chicken and Waffles, Chilaquiles, and Stuffed French Toast.
Date: Mon., Sept. 2Time: 11 a.m. - 2 p.m.Location: Cindy's Rooftop - 12 S. Michigan Ave.Price: Prices varyWebsite: cindysrooftop.com
Sunda New Asian Labor Day Brunch
Celebrate Labor Day weekend with a relaxing brunch at Sunda New Asian in River North. The Asian fusion hotspot is serving up brunch classics with a New Asian twist, including Ube Waffles, Japanese fried chicken, and its signature Island Breakfast Plate.
Date: Sat., Aug. 31, Sun. Sept. 1Time: 11 a.m. - 2 p.m.Location: Sunda New Asian - 110 W. Illinois St.Price: Prices varyWebsite: sundanewasian.com
Sweetwater Tavern and Grille’s Brunch
Enjoy city views while dining at this upbeat restaurant serving various brunch specials and drinks. Donuts, mimosas, and avocado toast are a few options from which guests can choose. Reserve tables through Open Table .
Date: Mon., Sept. 4Time: 11 a.m. - 3 p.m.Location: 225 N. Michigan Ave.Price: Prices varyWebsite: sweetwatertavernandgrille.com
The Hampton Social’s Brunch
The Hampton Social is hosting a Labor Day brunch special at both Chicago locations. Specialty cocktails, seafood, and sweet dishes like Monkey Bread are among many highlights. Reservations can be made here .
Date: Mon., Sept. 2Time: 11 a.m. - 3 p.m.Locations: 353 W. Hubbard St. (River North) and 164 E. Grand Ave. (Streeterville)Price: Prices varyWebsite: thehamptonsocial.com
Drink Specials
Post-Barbecue Labor Day Trivia at aliveOne
Cap off your Labor Day festivities with drink deals and free games at aliveOne in Lincoln Park. Starting at 8 p.m. guests can enjoy $6 and $7 drink specials along with free pool and music trivia.
Date: Mon., Sept. 2Time: 8 p.m. - 2 a.m.Location: 2683 N Halsted St.Website: aliveOne.com
Beer specials and Built-To-Grill Burgers at Estelle's
Estelle's is the place to be this Labor Day for late night munchies and dirt cheap beer deals. Starting at 10 p.m., guests can enjoy half-priced, built-to-grill burgers and $5 domestic beers all night.
Date: Mon., Sept. 2Time: 10 p.m. - closeLocation: 2013 W. North Ave.Website: estelleschicago.com
Labor Day Casual Cocktails at The Getaway
Lincoln Square's newest cocktail lounge is turning up the heat this Labor Day with its signature cocktail offerings and unmatched ambiance. Guests can stop by for a night cap and sample creative concoctions like the Spicy Bonkey (mezcal, lime juice, hot honey syrup, pineapple juice, ginger beer) or the Chai Chai Slide (Tito's vodka, Mr. Black coffee liqueur, Averna Amaro, housemade chai syrup)
Date: Mon., Sept. 2Time: 8 p.m. - closeLocation: 4530 N Lincoln Ave.Website: thegetawaychicago.com
Free Movies
Music Box Theatre
Chicago's historic Music Box Theatre is celebrating Labor Day with free movie screenings all weekend. On Saturday and Sunday, The Music Box will host free screenings of Weekend at Bernies, Paragon, and Between the Temples. Be sure to pre-register to secure your seats.
Date: Sat., Aug. 31 - Sun. Sept. 1 Time: Times varyLocation: 3733 N. Southport Ave.Website: musicboxtheatre.com
Festivals
Taste of Polonia
The largest Polish festival in the U.S. is back with authentic food, live entertainment, and much more. Indulge in delicious Polish cuisine from over thirty vendors, visit varied exhibits, and listen to live Polish music.
Date: Fri., Aug. 30 - Mon., Sept. 2Time: Times varyLocation: 5216 W. Lawrence Ave.Price: $15 for single day General AdmissionWebsite: topchicago.org
West Loop Art Fest
This diverse and interactive art festival returns to West Loop for the fifth year. Walk through four blocks of art, listen to live music, and enjoy wine tastings while kids can try some of the festival’s crafts for children.
Date: Fri., Aug. 30 - Sun., Sept. 1Time: Times varyLocation: West LoopPrice: FreeWebsite: starevents.com
Athletic Events
Chicago Cubs Game
Finish the long weekend at Wrigley Field as the Cubs take on the Pittsburgh Pirates.
Date: Mon., Sept. 2Time: 6:40 p.m.Location: 1060 W. Addison St.Price: Tickets starting at $27Website: tickets-center.com
Chicago White Sox Games
Visit Guaranteed Rate Field for a great game against the Detroit Tigers.
Date: Fri., Aug. 30 - Sep. 1Time: Various timesLocation: Guaranteed Rate Field - 333 W. 35th St.Price: Tickets start at $14Website: tickets-center.com
Fifth Third Bike the Drive
Start your morning by biking DuSable Lake Shore Drive with gorgeous views. Bike as much of the thirty-mile trail as you would like, and don’t forget to stop by the festival after your ride. The event supports Active Trans, a “non-profit advocacy organization working to improve conditions for walking, biking, and public transit throughout Chicagoland.”
Date: Sun., Sept. 1Time: 6:30–10:30 a.m. (biking), 8 a.m. – 12:30 p.m. (festival)Location: 235 S. Columbus Dr.Price: Prices varyWebsite: bikethedrive.org
Music
ARC Music Festival
With over sixty artists to choose from over three days, there’s music for everyone at Union Park. Presented by Auris, the festival includes names like Fatboy Slim, DJ Minx, and Kyle Walker. Passes can be purchased here .
Date: Fri., Aug. 30 - Sun., Sept. 1Time: 2 -10 p.m. each dayLocation: Union Park - 1501 W. Randolph St.Price: $199 single day General AdmissionWebsite: arcmusicfestival.com
Chicago Jazz Festival
A beloved Labor Day tradition, the Chicago Jazz Fest will take place between Millennium Park and the Chicago Cultural Center, bringing together local and global artists to honor one of the Windy City's most celebrated musical genres.
Date: Thu., Aug. 29 - Sun., Sept. 1Time: Times varyLocation: Millennium Park and Chicago Cultural CenterPrice: FreeWebsite: chicago.gov
North Coast Music Festival
Head to SeatGeek Stadium in Bridgeview to experience live music from names like Marshmello, Alesso, and DJ Snake. This three-day festival features many different artists and a unique, lively atmosphere. Buy tickets here .
Date: Fri., Aug. 30 - Sun., Sep. 1Time: 2 p.m. - 12 a.m.Location: SeatGeek Stadium, 7000 S. Harlem Ave. - Bridgeview, IL.Price: Prices varyWebsite: northcoastfestival.com
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