Chicago Labor Day Weekend 2019 – 10+ Fun Things to Do in September

Labor Day may mark the unofficial end of summer, but it certainly doesn’t mean the end of summer fun!

There are still so many great festivals, events, and activities to enjoy that will help you squeeze every last drop of summer out of this last weekend before school starts.

If you’re looking for Chicago Labor Day Weekend 2019 ideas, check out some of these local activities and fun things do in Chicago in September, including…

  • Architecture River Cruise
  • Architecture Tours
  • SkyDeck Chicago
  • Art Institute of Chicago
  • Navy Pier Centennial Wheel & Rides
  • Brookfield Zoo
  • Bike and Roll Chicago – 4 Hour Bike Rentals
  • Great American Lobster Fest at Navy Pier
  • Chicago Jazz Festival
  • And more!

1. Architecture River Cruise

The Chicago Architecture River Cruise cruising along the river

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!

2. Frank Lloyd Wright Studio & Robie House

The Frank Lloyd Wright Studio.If the idea of an architecture cruise was really exciting but didn’t seem to go far enough, you’ll want to check out some of Chicago’s other top architecturally-minded attractions.

Head to the Frank Lloyd Wright Studio and Home to tour the living and working spaces of one of the most iconic architects of the last century.

You can also scope out one of his famed local projects, the Robie House (on the campus of the University of Chicago, which is a fun area to explore as well).

Finally, the Chicago Architecture Center also offers plenty of walking tours, bus tours, Segway tours, and cruises to meet your architectural desires.

3. Art Institute of Chicago

The Art Institute of Chicago exterior
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 2019 include the highly-anticipated “Manet and Modern Beauty.” See our post on current exhibits at the Art Institute for more information.

4. Brookfield Zoo

A young girl looking at a polar bear behind glass.

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. Don’t miss their special exhibit, Amazing Arachnids, that showcases the art and science of arachnids now through September 3rd, 2018.

If you’re going to be around a bit before Labor Day, check out their popular Zoo Brew event. Hosted on August 24, 2019, this 21+ ticketed event allows animal lovers to sample tasty beers from top local breweries, with over 80 different drinks to choose from! There are also special prices and options for the designated drivers among you.

5. Rent a bike

A man and a woman riding bikes through greenery.
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.

6. SkyDeck Chicago

A woman on the Ledge at Skydeck Chicago.

Photo via Pinterest

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!

7. Navy Pier

Fireworks over Navy Pier at night.

Photo via Michael Norris

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.

Don’t miss the last Summer Fireworks Display on August 31, 2019! The show starts promptly at 10:15 pm, so make a whole day of it — ride the Centennial Wheel, explore the shops and dine along the boardwalk before the show starts.

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!

8. The Great American Lobster Fest at Navy Pier

An aerial view of Navy Pier with tents set up.

Photo via American Lobster Fest

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.

This event will be held from August 30 – September 1, 2019. General admission is free, although lobster meals and VIP tickets are also available for purchase.

9. Chicago Jazz Festival

A shot of jazz musicians on stage from behind.

A shot of the 2014 festival. Image credit: Chicago Jazz Festival Facebook page.

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).

This year’s festival runs from August 31 – September 1, 2019, just in time for Labor Day. Admission is free and open to the public.

10. North Coast Music Festival

The North Coast Music Festival brings together artists from all across the spectrum of EDM music. The 2019 ineup is filled with big names and top acts like Major Lazer, Bassnectar, Flux Pavilion, and many many more.

It’s also located on the chic Northerly Island concert site, which is an outdoor venue that’s just perfect for end-of-summer fun.  This year’s festival will run August 30-31, 2019.

The North Coast Music Festival is a separately ticketed event, with options for lawn seating, general admission, and VIP tickets.

Save on Attraction Admission

Regular admission to a number of these Chicago attractions are included on the Go Chicago® pass.

Choose as you go from dozens of top attractions and save up to 45% on combined admission vs paying at the gate.

See all available passes, attractions & prices – Learn more.

We hope you consider visiting some of these attractions to help round out your summer vacation in style.

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The information contained in this post, to the best of the author's knowledge, was accurate at time of publishing. We do our best to ensure and maintain the accuracy of this information.

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