Things To Do
Chicago Jazz Festival
The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival boasts an incredibly diverse lineup of jazz legends and fresh talent — making it a true bucket list event for jazz fans.
Bike down Lake Shore Drive
Enjoy a scenic ride down Chicago’s stunning DuSable Lake Shore Drive, which is shut down to cars just one day each year. Bike the Drive on Sunday, Sept. 1 features a 30-mile loop on the iconic road, inviting bikers to enjoy a long or short ride while taking in views of the lake and city skyline. No wheels? No problem. Bike rentals are available.
Chicago SummerDance
This summer-long event series brings people together in the city’s scenic parks for evenings filled with music, dance, community, and celebration. Each event features lessons from a professional dance instructor, featuring more than 30 unique dance styles from around the globe.
Take a Chicago boat tour or cruise
Set sail on one of Chicago’s scenic boat cruises on our two sparkling waterfronts. Choose from informative architecture tours, fast-paced speedboat rides, unforgettable dinner cruises, tiki-themed party boats, sunset and fireworks cruises, and more. We recommend Groupon for good deals.
Wander the Chicago Riverwalk
Where else can you find an urban canyon filled with delicious food, cocktails, public art, and stunning views? The Chicago Riverwalk is open to enjoy all Labor Day weekend long. It’s the perfect spot to hop on a boat tour, admire the surrounding architecture, and enjoy a drink with waterfront views. The popular waterfront restaurants and bars are open for just a little longer, so make your reservations now.
Visit a Museum
Which Chicago museum is on your bucket list? The long weekend is the perfect time to visit one of the city’s world-class museums that let you immerse yourself in everything from avant garde works at the Museum of Contemporary Art to fascinating ancient history at the Field Museum to interactive exhibits at the Griffin Museum of Science and Industry and beyond.
Visit out favorite Brewery
This is our favorite brewery. It has a nice outdoor patio and it is BYOF (bring your own food).