Chicago Labor Day Weekend 2018 – 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 2018 ideas, check out some of these local activities and fun things do in Chicago in September, including…

  • Architecture River Cruise
  • 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!

Save on Attraction Admission

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

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.

Please note, the special events taking place at these attractions may be separately ticketed and not included on the Go Chicago Card.

Architecture River Cruise

The Chicago Architecture River Cruise cruising along the river

Explore Chicago’s unique architecture aboard a Shoreline river tour.

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!

Getting in: Architecture River Cruise tickets are included on Go Chicago Card.

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.

Getting in: Art Institute of Chicago tickets are included on Go Chicago Card.

Brookfield Zoo

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.

The Brookfield Zoo also host tons of fun events, like the ZooRunRun for Animal Care and Conservation Fund. On September 9th, 2018 you can join the run to raise money for a great cause and bring your family to cheer you on!

Getting in: Brookfield Zoo tickets are included on Go Chicago Card.

Rent a bike

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.

Rent a bike from Navy Pier and pedal along the waterfront and the many miles of lakefront trails in the area.

Getting In: Bike and Roll Chicago – 4 Hour Bike rentals are included on the Go Chicago Card.

SkyDeck Chicago

Photo via Pinterest

Journeying to the top of the Willis Tower and stepping out on The Ledge is a must on any Chicago vacation.

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!

Getting in: SkyDeck Chicago tickets included on Go Chicago Card.

Navy Pier

September 1st – 3rd, 2018

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 Summer Fireworks Display on September 1st, 2018! The show starts promptly at 10:15pm, so make a whole day of it – ride the Centennial Wheel, explore the shops and dine along the boardwalk before the show starts.

Navy Pier will also be hosting Music on the Lake all Labor Day Weekend. Swing by the Miller Lite Beer Garden for free live music, dancing and drinks.

Getting in: Navy Pier Summer Fireworks and Music on the Lake celebrations are open to the public. Navy Pier Centennial Wheel & Ride tickets are included on Go Chicago Card.

The Great American Lobster Fest at Navy Pier

August 31st – September 2nd, 2018

Photo via American Lobster Fest

Now in its 5th 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 topnotch lobster and seafood dishes, live performances, family games, arts and crafts and more.

While you’re at Navy Pier, explore some of its great attractions to. Ride the Centennial Wheel, visit the Chicago Children’s Museum or shop around.

Getting In: The Great American Lobster Fest is a separately ticketed event. Navy Pier Centennial Wheel & Ride tickets and Chicago Children’s Museum tickets are included on Go Chicago Card.

Chicago Jazz Festival

August 29th – September 2nd, 2018
Millennium Park and Chicago Cultural Center

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

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 37 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 Millenium Park, home of the famous Cloud Gate Sculpture (otherwise known as The Bean).

Getting In: Admission to the Chicago Jazz Festival is free.

Chicago Fringe Festival

August 30th – September 3rd, 2018
Jefferson Park

Photo via Chicago Reader

The Chicago Fringe Festival celebrates the art of live performance. See theater, dance, puppetry, stand-up and spoken word performances by local artists of all kinds.

All of the material at Fringe is original and fresh. It’s a great way to find local artists and creators!

The Fringe Festival also boasts a Kids Fringe section with kid-friendly performances, activities and workshops.

Getting in: The Chicago Fringe Festival is priced per performance, at roughly $10/ticket. All proceeds go directly to the performing artists.

North Coast Music Festival

August 31st – September 2nd, 2018
Union Park

The North Coast Music Festival brings together artists of every genre.

From folk to rock to hip hop, you’re favorite artist will be here no matter what kind of music you’re into. See Axwell X Ingrosso, Miguel, Midnight Conspiracy Cover Band, DJ Snake and more in the 2018 lineup.

Getting in: the North Coast Music Festival is a separately ticketed event.

Remember to Save on Attraction Admission

There you go – plenty of fun ideas for things to do in Chicago in September to help you plan your Labor Day weekend itinerary.

While you can clearly enjoy a plethora of great cultural activities completely for free, there’s probably plenty you want to see and do that does require admission.

Remember, most of these great attraction options are included on the Go Chicago Card, where you can save up to 45% on combined admission vs paying at the gate.

Please note, the Labor Day weekend events taking place at some of these attractions may be separately ticketed and not included with the Go Chicago Card.

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

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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