Things to Do on Labor Day Weekend in Chicago

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.

If you’re lucky enough to spend the holiday in Chicago, we’ve put together a list of things to do for Labor Day in the Windy City this summer.

Plan on doing a lot of exploring while you’re in town? Be sure to pick up an all-inclusive Go Chicago® Card to save big on admission to all of the top cruise, tours, museums, and more.

Special Events

Millennium Park Music Festival

June – August
Millennium Park

Millennium Park Chicago

Summer in Millennium Park

While this festival lasts all summer, its concluding weekend coincides with Labor Day this year, so it’s a good opportunity to get in a little bit more free music.

You’ll be able to enjoy several themed series throughout the summer, and during the last weekend of the festival the theme is “Made in Chicago: World Class Jazz.”

The whole family will love this fun free event – don’t forget to bring a picnic dinner with you!

Summer Film Series

June 23 – September 1
Priztker Pavilion

Another great free event in downtown Chicago, the Summer Film Series will be wrapping up the weekend before Labor Day. Enjoy modern classics from all genres, including everything from Apollo 13 to Almost Famous.

The last film of the series is one of our favorites, The Breakfast Club. BYOP (Bring Your Own Popcorn)!

Chicago SummerDance

June 26 – September 13
Grant Park

Each summer the Spirit of Music Garden in Grant Park opens to host an exciting urban dance space that features live performances from 44 different bands (over the course of the summer).

Dance your heart out free style, enjoy dance lessons, or just sit back and soak up the music.

It’s a fun way for the whole family to be active, even if it’s only for a short while. As you catch your breath, take a seat on the sidelines and enjoy people-watching. Another totally free and totally awesome event!

Chicago Jazz Festival

September 3 – 6
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 free thing to do this Labor Day weekend, especially for fans of the arts and culture scene.

Things to do Outdoors

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!

Bike Rides

Enjoy beautiful lakefront trails.

Enjoy beautiful lakefront trails.

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.

Sightseeing Cruises

Just because you aren’t near an ocean doesn’t mean you can’t enjoy some quality time on the water! Chicago is well known for its iconic waters, from Lake Michigan to the famed Chicago River.

Enjoy your time afloat with a lake cruise or river cruise, which can be both informative and relaxing. (Bonus – you can get that last little bit of tan, too.)

Navy Pier

Navy Pier

Everyone loves the family fun at Navy Pier!

It’s one of the most famous sites in the city for a reason. Navy Pier’s fun and festive atmosphere is delightful year round, but perhaps most of all during the summer months.

You can enjoy a ride to the very top of the instantly-recognizable Ferris wheel, a few swing rides, and even some mini golf.

Or, explore great attractions on the Pier itself like the Chicago Children’s Museum, the Chicago Shakespeare Theatre, and an IMAX Theater. There’s plenty to eat and drink, too.

Chicago Tours

There is so much beauty to be found in Chicago - just enjoy it!

There is so much beauty to be found in Chicago – just enjoy it!

If you’re a visitor to Chicago, why not take advantage of the great weather to get to know a little bit more about the city? Choose from a wide variety of tours that cover various geographic parts of the city (like a North Side tour or a South Side tour) or a cultural aspect (like an architecture tour or a theatre tour).

Save on Admission

While you can clearly enjoy a plethora of great cultural activities without spending a dime, there’s probably plenty you want to see and do that does come with a price tag.

Fortunately for you, the Go Chicago® Card is a great way to save big on admission to all your favorite tours, cruises, and attractions. Be sure to pick one up today!

Go Chicago Card

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