Labor Day weekend in Chicago signals that the dog days of summer are almost behind us. While we might feel glum that this summer went by faster than the last, we still have one long weekend to make the most of it. Between dancing to pulsating beats, sipping a dirty martini across from the river, or lounging on a rooftop pool, there are plenty of things to do in Chicago Labor Day weekend, from August 30th to September 2nd. Here are some ideas to consider for your extra day off.
1. Booze on a river cruise while you still can
Celebrate Labor Day correctly—sipping a Modelo with a lime slice with the Chicago skyline in the background. What could be better, truly? Whether you want to sail or speed, there are various boats to rent from in Chicago or (if you don’t want to be your own captain) booze cruises for the day!
2. Dance all weekend at Arc Festival
You might not know, but Chicago has a long history of house music—in fact, its birthplace was here—and this year marks the 40th anniversary of house music. Returning to the heart of the city at Union Park this Labor Day Weekend in Chicago, ARC’s fourth iteration will be soundtracked by the world’s leading house and techno selectors.
Some of the featured artists in the lineup are Disclosure, Carl Cox B2B Green Velvet, Skepta, Honey Dijon, Charlotte de Witte, Dom Dolla, Sven Väth, Purple Disco Machine, Gorgon City, Kaskade Redux, Jayda G, and LP Giobbi.
3. Lounge at a rooftop pool
It seems like yesterday that rooftop pool season officially commenced. Sadly, that was almost three months ago, and we’re nearing the end of pool season. These hotels and workout facilities are sprinkled around the city; some are free, and others require a fee. We’ve listed the best ones in Chicago this Labor Day weekend.
4. Catch the last Navy Pier fireworks
Chicago’s favorite sky spectacle ends this Labor Day weekend. If you haven’t already, this is your last chance to catch the 10 p.m. fireworks showing at Navy Pier. Watch an abundance of colors light up the sky right over the water. You can go directly to the pier or head to the lakeshore front for a spectacular show.
5. Soak up the last summer beach days
Head to one of these Chicago beaches while the air is still humid and water is the quintessential escape. However, it might be one of the last days to do it, so snag a towel to lay out, purchase a paddleboard to rent for a few hours, or hit the lake on a jet ski as you stuff your feet into the sand and bask in the warm sun rays.
6. Dine out on the riverwalk
While the riverwalk will get a bit nippier in the coming months, there’s no time to enjoy it more than the present. Our famous riverwalk is filled with stunning restaurants and bars, from bohemian hideouts to wine bars. It’s the perfect spot to dine outdoors right by the water.
7. Be memorized by art at the West Loop Art Fest
West Loop is a lively and vibrant neighborhood in Chicago, and this weekend, their Art Fest returns for its sixth year on Saturday and Sunday, August 30st to September 1st. The ambient evening will have a diverse range of art, wine tasting, live music, and more; it’s a lovely event if you’re in the mood for late summer shopping. Whether you want to spend the whole day there or hop to Fulton Market afterward for some drinks, it’s one of our favorite things to do in Chicago Labor Day Weekend.
8. Get groovy at a four-day Jazz Festival
The free summer music festival lineup at Millenium Park continues with the Chicago Jazz Festival. Returning with performances celebrating all forms of jazz in Millennium Park, at the Chicago Cultural Center, and citywide. If you love the sounds of instruments battling one another and creating a sweet melody, this is your quinessential Labor Day Weekend event. Produced by DCASE and programmed by the Jazz Institute of Chicago (JIC).
9. Grab a Perogi at Taste of Polonia
The largest Polish festival in the U.S. returns to Chicago this Labor Day weekend. This annual 4-day weekend taste fest offers live music and polish delights. Along with carnivals, games, a casino, exhibits, and more, there will be over 30 vendors serving delicious Polish-forward food, and a craft beer tends to pair with it.
10. Sip drinks on a rooftop bar
Take advantage of the last few weeks to sip in style with the sun on your side before you’re situated next to heat lamps. There are an array of places to booze at, from sumptuous hotel terraces to adult playground lounges. Take in the best breathtaking views at rooftop bars in Chicago Labor Day weekend for a little inebriation and banter with friends.
11. Get sporty at a baseball game
While the Chicago Bears don’t officially start until September 8th, sports fans can relish in the last few months of baseball for the time being, and luckily, Chicagoans have two teams they can root for in Chicago Labor Day weekend. The White Sox play at home this weekend and have a series against NY Mets, while the Cubs play at home the latter half on September 2nd against the Pirates and Yankees.
12. African Festival of the Arts
The African Festival of the Arts, which celebrates art, music, and food from across the African diaspora, will return this Labor Day weekend in Chicago. The festival will take place in Washington Park and will feature a recreated African village with vendors, stilt walkers, African fine art and fabrics, a quilt pavilion, drum circles, and other interactive features. Attendees can enjoy live music from various acts. Additionally, there will be a Bank of the Nile food court with food from across the African continent and beyond.
13. aliveOne Hosts Post-Barbecue Labor Day Trivia
After the Labor Day barbecues, head to aliveOne in Lincoln Park at 8 p.m. to sip on $7 PBR and whiskey shot combos while they play free music trivia with Whaddayaknow Trivia. Afterward, you stick around to play free pool until close!
14. Late-Night Labor Day Party at The Owl
Guests looking for a late-night Labor Day party can head to The Owl in Logan Square from 10 p.m. until 4 a.m. on Monday, September 2. Guests can sip on seasonal cocktails like the Moonstruck with Old Overholt Rye Whiskey, Aperol, Meletti Amaro, pineapple, lime, and simple syrup or the Legally Blonde with Beefeater Gin, New Deal Ginger Liqueur, passionfruit, lemon, and simple syrup.
15. Late-Night Built-To-Grill Burgers at Estelle’s
For Chicagoans looking for some late-night Labor Day munchies, Estelle’s in Wicker Park will open at 10 p.m. on Monday, September 2. Guests will enjoy a late-night barbecue with half-price burgers, built-to-grill, and $5 domestic beers all evening.