For many in the U.S., Labor Day weekend officially means the end of summer is nearing, so we better take advantage of the warmth and Chicago summer festivals while we still can. There’s definitely no shortage of things to do. In fact, it might be quite saturated and hard to decide what to do in Chicago Labor Day weekend. The holiday falls on September 1-4, and to help you celebrate (and narrow down your list), we’ve rounded up the best events to check out in the city this weekend!
Celebrate Labor Day the right way with a fun party cruise on the Chicago River. Whether you want a classic Sunday booze cruise, a place to belt out to T-Swift, or hear the history of Chicago architecture—all with a drink in hand—there are a ton of booze cruises to choose from in Chicago Labor Day weekend!
2. Dance all weekend at North Coast
Ask any Chicagoan, and chances are they’ve heard of the North Coast Music Festival. The annual house and electronic music festival is held on Labor Day weekend every year and always hosts incredible prominent artists. This year features Alesso, Flume, Marshmello, DJ Snake, and more.
It seems like yesterday that rooftop pool season officially commenced. Sadly, that was almost three months ago, and we’re nearing the end of rooftop pool access. 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 Labor Day weekend.
4. Catch the last Navy Pier fireworks
Chicago’s favorite sky spectacle ends this 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.
It’s some of the last days to soak up the sun! 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 to have an amazing weekend with your feet in the sand.
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.
Spend your day off this Labor Day weekend cosplaying as a detective and solving a murder! CLUE: A Walking Mystery will transport you into a thrilling adventure where you’ll be navigating through a real-life setting trying to solve the homicide of Mr. Boddy. It will be a Labor Day weekend experience you won’t forget!
8. 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 fifth year on Saturday and Sunday, September 2nd and 3rd. It’s a lovely event for some late summer shopping. The ambient evening will have a diverse range of art, wine tasting, live music, and more! Whether you want to spend the whole day there or hop to Fulton Market afterward, it will be splendid!
We’re sad to see it leave, and if you haven’t had a chance to go—this is your last weekend to experience the wonders of Harry Potter™! If you’re wondering what to do with your kids on their day off, take them to this hands-on experience that will bring out their inner wizard. As they explore and play through the Harry Potter™ books and movies, they might never want to leave—and will probably say Patronus all the way home.
10. Get groovy at a four-day Jazz Festival
The Chicago Jazz Festival returns with performances celebrating all forms of jazz in Millennium Park, at the Chicago Cultural Center, and citywide. This is for you if you love the sounds of instruments battling one another and creating a sweet melody. Produced by DCASE and programmed by the Jazz Institute of Chicago (JIC), this is one of our favorite free things to do in Chicago.
11. Grab a Perogi at Taste of Polonia
The largest Polish festival in America returns to Chicago Labor Day weekend. This annual weekend taste fest offers live music, food, and an entertainment-filled four days. 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.
This is one of the last weekends 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.
Arc Festival is taking place Friday, September 1 – Sunday, September 3, and will be heading into its third year with a star-studded lineup that is sure to cement the festival’s place as a fan-favorite in the global festival circuit. Some of House Music’s biggest DJs will be gracing the ARC music stages this year, including Peggy Gou, Nina Kraviz, and Anfisa Letyago.
14. Get sporty at a baseball game
While the Chicago Bears don’t officially start until September 10th, 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 Detroit Tigers September 1-3, while the Cubs play at home the latter half on September 4th against the Giants.