End of Summer: 7 Things to Do in Chicago in September


Few people know about the Great Chicago Fire. It destroyed 17,000 buildings in 1871 and killed 300 people. But there was some good to come from it: the city rebuilt itself.

Post-fire, Chicago is a must-see destination for Americans as much as tourists. It’s a center for arts, incredible pizza, and some to-die-for architecture that she won’t find in Manhattan. That said, Chicago is known as the “Windy City” and gets quite chilly in fall and winter.

What are some things to do in Chicago in September before the temperature drops too much? In this guide, we’ll talk about seven things you should do when visiting Chicago this fall.

Things to Do in Chicago in September 1: Take a Cruise

The Chicago River has a world-renowned reputation thanks to one simple fact: they paint it green every year. This St. Patrick’s Day celebration makes the boats look like they’re floating on a river of Kool-Aid. But no matter what time of year, Chicago is an excellent place for a lunch cruise.

The river takes you right through the middle of the city. It passes by many of the major landmarks, minus the hassle of traffic. Plus, you get the peace and quiet you can only find out on the water.

A cruise can take you out onto Lake Michigan. You’ll get a slice of that gorgeous Great Lakes nature and some wonderful salty beaches. Oh, and of course, you get lunch. Who wouldn’t want a meal made by some of Chicago’s best chefs?

2: Watch Some Sports

No late summer trip is complete without seeing a game or two. Chicago is home to many of the most famous teams you recognize. It has the White Sox, Cubs, Bulls, and more.

If you’re looking for things to do in September, then drop by a stadium. You can watch baseball, basketball, and even soccer if you like. Best of all, you have some excellent post-game cuisine to choose from.

In the meantime, you can drop by the Hall of Fame and sports museums. Pay tribute to the world’s athletes, past and present.

3: Go to a Jazz Festival

Jazz is to Chicago as hot dogs are to New York. The genre may not have been born here, but it has certainly flourished. Many famous jazz musicians got their chops in this city.

Each year, the municipality hosts a free jazz festival at Millennium Park. It’s a family-friendly event featuring famous names in the jazz scene alongside local ones. In terms of budget-friendly summer ideas, this is one of the best.

jazz festival

If you miss that festival, there are still two more hosted in September. At the end of the month, you have both the Hyde Park Jazz Festival and the Jazzin on the Steps.

4. Oktoberfest

Oktoberfest in Chicago does not actually happen in October. It runs between the 8th and 10th of September at Lincoln Square. Needless to say, you will still be getting the full experience.

Oktoberfest may be a German beer tradition, but it’s alive and well in Chicago. Come for the music and food. Then stay for the parade, in operation since 1920.

Make no mistake, Oktoberfest is for lightweights as much as connoisseurs. You can try tons of free craft beer from local breweries. If you’ve ever wanted to dress up like a German from centuries past, this is your chance.

5. Take Part in Harry Potter: Magic at Play

Unbeknownst to many, the Harry Potter franchise has been running a little-known Magic at Play event exclusively in Chicago. That ends this September. Make sure you sign up early before this limited-time opportunity disappears forever.

You will need tickets for this one, but it’s an event for all ages. The venue describes itself as a hands-on experience in the Wizarding World.

Inside the venue space, there are three floors dedicated to places and moments in Harry Potter history. There will be exploration, climbing walls, and dueling halls to practice your magic.

6. Take the Kids to Navy Pier

Navy Pier is Chicago’s version of Coney Island. It’s a tourist trap, make no mistake. A place you go to get that one picture that proves you were in Chicago.

Whatever the case, though, it’s a great place for kids. There are Ferris wheels, boat rides, and plenty of food to enjoy as you stroll the pier. While you’re there, don’t miss the Chicago Children’s Museum. There are also plenty of restaurants and shops to keep the adults busy while the kids are at play.

This also happens to be the launching point for most river and lake cruises. If you go early in the morning, you can finish off the day with a lunch or dinner cruise, as mentioned above.

7. See Chicago from the 360 Chicago Observation Deck

Before you go, it’s important to see this incredible city from the skyline. The best and cheapest way to do so is from the John Hancock building. Up on the 94th floor, you will find 360 Chicago, a glass-bottomed observation deck that circles the building.

Every city has an observation deck like this, from New York to Seoul. Conquer your acrophobia by standing on the thick-paned glass to see the city between your feet. Make sure to snap plenty of photos of the city as it stretches out to Lake Michigan.

This one is free, too. However, we recommend purchasing your ticket in advance. Lines can be quite long, and a ticket allows you to skip them.

Visit Chicago Today

Needless to say, there are plenty of things to do in Chicago in September. A Chicago vacation lets you take part in the city’s long history as a cultural, artisanal, and culinary American capital. Enjoy your lunch cruises, music festivals, and everything in between.

Follow our blog for more great travel tips.

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