Chicago Labor Day Weekend - 10+ Fun Things to Do in September

Explore Chicago's unique built environment aboard a Shoreline architecture river cruise. You'll sail down all three branches of the Chicago River and see iconic buildings by Mies van der Rohe, Skidmore Owings Merrill, Bertrand Goldberg and more. The Windy City is well-known for its famous architects and their advancements in the field. There's no better place to take in some of the world's finest buildings and structures!

If you're looking to infuse a bit of culture into your Labor Day weekend vacation, then a visit to the world famous Art Institute of Chicago is a smart choice. This award-winning museum is filled with diverse collections of amazing works of art and historical artifacts, from Asian statuary stretching back millennia to modern American and European painting. Some of the summer exhibits they'll have running through Labor Day include the highly-anticipated "Manet and Modern Beauty." See our post on current exhibits at the Art Institute for more information.

The Brookfield Zoo is the city's largest zoo! The 216-acre park is home to a variety of animals, from Big Cats to the Great Bear Wilderness. See all your favorites, big and small, at exhibits like the Seven Seas or Living Coast.

Of course there’s no place you’d rather be on Labor Day weekend than soaking up the last of the summer sun, so why not spend most of your time outside? There is so much to see and do in the great urban outdoors that is Chicago, so take your pick! Taking a bike for a spin is one of our favorite summer activities. It keeps everyone fit and healthy and is tons of fun to boot. Opt to rent a bike from Navy Pier and pedal along the waterfront and the many miles of lakefront trails in the area. They're immensely popular with cyclists, runners, and strolling families from all across the city, so it's an nice opportunity to see what the locals get up to as well.

Journeying up to the top of the Willis Tower to SkyDeck Chicago and stepping out on The Ledge is a must on any Chicago vacation. This impressive observatory is one of the best in the city. Keep in mind that the Ledge attraction is one for the bravest among you -- you'll step out onto a solid glass floor that looks down onto the city below. At 1,353 ft in the air you'll see the Windy City in its entirety. From Navy Pier to Soldier Field, Chicago will be at your feet. Make sure you bring a camera!

Navy Pier is the quintessential Chicago attraction. It's a great place to visit no matter the season, but its especially lively throughout the summer. If you're traveling with kids, remember that the Chicago Children's Museum is also located on Navy Pier, making it a nice addition to a day of rides and fun for the kids. For the adult groups, be sure to visit the Offshore Rooftop & Bar, located on the third floor of the Festival Hall. It's a hot new venue for summer drinks and bites that's just opened earlier this year and is a must-visit. Plus, it's the largest rooftop bar in the country, so what's not to love? Check out our guide to Navy Pier for more complete information!

Now in its 6th year, the Great American Lobster Fest returns to Chicago's iconic Navy Pier. It's an event you won't want to miss. The Great American Lobster Fest is the largest lobster and seafood festival in the Midwest. Head down to Navy Pier this Labor Day Weekend to kickoff the end of summer with top notch lobster and seafood dishes, live performances, family games, arts and crafts and more. General admission is free, although lobster meals and VIP tickets are also available for purchase.

This longtime lakefront music festival is a Chicago legend. It’s also been a Labor Day tradition for nearly 40 years, so it’s an important part of the way the city celebrates this great summer holiday. You’ll enjoy free live music performances that range through all varieties of jazz, from local and even international musicians. A visit to this iconic Chicago event is yet another wonderful thing to do this Labor Day weekend, especially for fans of the arts and culture scene. It's also a great excuse to head over to Millennium Park, home of the famous Cloud Gate Sculpture (otherwise known as The Bean).