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. 2
• Time: 11 a.m. - 2 p.m.
• Location: Cindy's Rooftop - 12 S. Michigan Ave.
• Price: Prices vary
• Website: 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. 1
• Time: 11 a.m. - 2 p.m.
• Location: Sunda New Asian - 110 W. Illinois St.
• Price: Prices vary
• Website: 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. 4
• Time: 11 a.m. - 3 p.m.
• Location: 225 N. Michigan Ave.
• Price: Prices vary
• Website: 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. 2
• Time: 11 a.m. - 3 p.m.
• Locations: 353 W. Hubbard St. (River North) and 164 E. Grand Ave. (Streeterville)
• Price: Prices vary
• Website: 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. 2
• Time: 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. 2
• Time: 10 p.m. - close
• Location: 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. 2
• Time: 8 p.m. - close
• Location: 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 vary
• Location: 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. 2
• Time: Times vary
• Location: 5216 W. Lawrence Ave.
• Price: $15 for single day General Admission
• Website: 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. 1
• Time: Times vary
• Location: West Loop
• Price: Free
• Website: 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. 2
• Time: 6:40 p.m.
• Location: 1060 W. Addison St.
• Price: Tickets starting at $27
• Website: tickets-center.com

Chicago White Sox Games

Visit Guaranteed Rate Field for a great game against the Detroit Tigers.

• Date: Fri., Aug. 30 - Sep. 1
• Time: Various times
• Location: Guaranteed Rate Field - 333 W. 35th St.
• Price: Tickets start at $14
• Website: 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. 1
• Time: 6:30–10:30 a.m. (biking), 8 a.m. – 12:30 p.m. (festival)
• Location: 235 S. Columbus Dr.
• Price: Prices vary
• Website: 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. 1
• Time: 2 -10 p.m. each day
• Location: Union Park - 1501 W. Randolph St.
• Price: $199 single day General Admission
• Website: 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. 1
• Time: Times vary
• Location: Millennium Park and Chicago Cultural Center
• Price: Free
• Website: 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. 1
• Time: 2 p.m. - 12 a.m.
• Location: SeatGeek Stadium, 7000 S. Harlem Ave. - Bridgeview, IL.
• Price: Prices vary
• Website: northcoastfestival.com