Summer is winding down and Labor Day is fast approaching, meaning it’s time to plan your last hurrah!
There’s no shortage of ways to spend your holiday, from bar hangs to brunch specials and more. Here’s your 2025 guide to Labor Day events in Chicago.
Brunch and dining deals
This Labor Day is the perfect occasion to score some deals at your favorite brunch spots in Chicago! Here are a few a spots offering cheap cocktails, dollar oysters, and other deals Labor Day weekend.
- Costera Cocina Tulum (850 W Fulton Market) – Enjoy happy hour specials and a live DJ from open to close on Monday, September 1. Guests will enjoy $10 margaritas and espresso martinis, along with discounted bites like salmon tostadas, asada tacos, and more.
- Nisos Prime (802 W Randolph St) – Nisos Prime Bar is celebrating Labor Day with food and drink specials and live DJ music all day on Sunday, August 31. Guests can take advantage of $1 oysters, $15 Waygu smash burgers, $12 martinis, and half price bottles of wine.
- Aura on the Lake (Kathy Osterman beach) – Soak up the last days of summer with Aura on the Lake at Kathy Osterman beach from Friday, August 29 through Monday, September 1. Guests can enjoy seasonal fare and cocktails every day on Aura’s outdoor patio, with live DJ music on Friday and Sunday. Bring your pup along too!
- The Hampton Social (River North and Streeterville) – The Hampton Social is throwing a special Labor Day brunch on Monday, September 1, offering the perfect way to close out the weekend. Guests can enjoy signature plates like wild berry French toast, lobster rolls, along with seasonal cocktails.
Happy hours and bar hangs
What better way to relax this labor day than with cheap drinks at some of your favorite local bars? Here are all the spots offering half price happy hours, trivia, dance parties, and more.
- aliveOne (2683 N. Halsted St.) – $7 drink specials, plus free trivia and pool on Monday, September 1.
- Central Park Bar (2924 N. Central Park Ave.) – Half-price happy hour on Monday, September 1.
- Cody’s Public House (1658 W. Barry Ave.) – Cubs pregame party on Monday, September 1. $5 Old Style tall boys, $7 Malört shots, and $7 Cubby Bombs.
- Easy Bar (1944 W. Division St.) – Half-price happy hour from 4-6 p.m. on Monday, September 1. $4 Montucky Cold Snacks, $5 shots of Espolón Blanco, $5 Underberg, and $9 beer and shot combos.
- Estelle’s (2013 W North Ave.) – Late night burger barbecue on Monday, September 1 beginning at 10 p.m. Guests can enjoy a half-priced burger with the purchase of any drink.
- Remedy (1910 N. Milwaukee Ave.) – $5 draft specials all night long.
Street festivals
Labor Day in Chicago coincides with some of the city’s favorite annual street festivals. From live music to cultural fairs, here are the best events taking place over the long weekend:
- Taste of Polonia – Chicago’s largest Polish festival is back from August 29 – September 1, bringing four days of great food, live entertainment, and family fun to Jefferson Park.
- Chicago Jazz Fest – Chicago’s favorite end-of-summer tradition returns to Millennium Park this Labor Day Weekend with headliners esperanza spalding, Kermit Ruffins, and more.
- Duck Fun Day at Waukegan Harbor & Marina – Waukegan Harbor & Marina is celebrating its 40th anniversary on Saturday, August 30 with the “Duck Fun Day” festival and a visit from “Mama Duck”—the world’s largest traveling rubber duck inflatable.
