How to Spend 24 Hours in Chicago

Disclaimer: This post contains affiliate links from which we may make commission from. As always, we only recommend places and products we love!

How to Spend 24 Hours in Chicago

Only 24 hours in Chicago you say? Well, that’s all the time to explore when we had when we visited for a quick weekend to see a concert right after we returned from Japan.

Yeah, we might be bonkers to head off again so soon after a big trip but we did it anyway! We quickly unpacked, repacked, and hitched a ride on the Amtrak from St. Louis to Chicago. Let’s just say that public transit in the United States is much less appealing and s-l-o-w in comparison to that of Japan. 😉

When we first arrived we quickly took the next train to the Ravinia Festival, an outdoor amphitheater located in Highland Park. When thinking about most of the outdoor amphitheaters we have been to they have typically all had a decent lawn seat (unless of course, you’re at Woodstock, Lollapalooza, or Bonnaroo).

However, the Ravinia Festival was not what we expected. Instead, we found ourselves surrounded by a huge crowd of people! We thought we would be only hearing the concert from the outdoor speakers until we had a bit of luck. We met a couple who were season ticket holders for the Ravinia. They were able to get us inside in a quicker line and helped us get terrific seats as close as we could to the stage.

Since it was late when the concert was over we decided to head back to our hotel near the Ravinia to get a decent night’s sleep as we knew we’d be rushing all over the city the next day!

The next morning we had a little less than 24 hours to enjoy as much as we could in Chicago so we headed towards downtown Chicago.

Top Things to Do in 24 hours in Chicago

Visit The Expansive Millennium Park

During our 24 hours in Chicago, we spent most of our time exploring the Millennium Park area. Millennium Park is by far one of the most popular attractions in downtown Chicago offering ample green space for picnics, reading, or lounging, sculptures and art installations, a splash area to help combat the summer heat, and even free concerts and movies during certain times of the year.

A Few Popular Attractions in Millenium Park

Cloud Gate

Cloud Gate, also known as “The Bean” is one of the most iconic places within Millennium Park. Typically when people think Chicago, this one of the first images that come to mind. Cloud Gate was created in 2004 by Sir Anish Kapoor who got his inspiration for Cloud Gate was from liquid mercury. It is made from 168 steel plates that were welded together and polished thus making it the perfect place for a selfie. 😉

Crown Fountain

Crown Fountain is really close to Cloud Gate and an incredibly popular to visit during the summer but is open from May-October each year. Not only is it a splash zone where you can cool off during the hot summer months, but it is also a piece of interactive art. It was designed by artist Jaume Plensa and opened in July 2004.

Jay Pritzker Pavilion

While we didn’t get to enjoy entertainment at Jay Pritzker Pavilion during our 24 hours in Chicago this is something that is perfect to add to your itinerary for a weekend in Chicago, especially in the summer. Each summer, the City of Chicago hosts various summer film and music series – most of which are free to attend. However, even if there isn’t an event it’s a great space to relax or have a picnic.

Enjoy Chicago-style Deep Dish Pizza

Of course, while in Chicago you can’t miss out on having some Chicago-style pizza. One of my favorites is Lou Malnati’s but Gino’s is another favorite of too. The thing about pizza, especially cities known for their pizza, is that everyone has their preference. So I hope to try a few additional pizza places in Chicago the next time I visit. 🙂

Regardless, Chicago-style pizza is a deep-dish pizza giving it a high crust. It is then loaded with cheese and topped with chunky tomato sauce and other toppings which is different than most pizza you’ll try in the U.S.A. which has sauce first, then cheese.

Explore the Art Institute of Chicago

The Art Institute of Chicago was founded in 1879 making it one of the oldest art museums in the United States. It is also a highly regarded place to visit during a weekend in Chicago. It features art from around the world with collections featuring Japan, China, Greece, Africa, and the Americas including one of the greatest Impressionist art collections in the world.

Experience and Learn From the Chicago Cultural Center

The Chicago Cultural Center is located inside a stunning building that was originally built in 1897 as the first public library of Chicago. Each year there are many performances and cultural exhibits such as classical concerts and oral history projects for visitors to attend for free.

Cost: Free to visit

Grab A Snack for the Road at Garrett Popcorn

Before hitting the road make sure you stop by one of the Garrett Popcorn shops in Chicago which first opened in 1949! Sure, getting this popcorn is a little touristy but it makes for an excellent snack if you can take with you on a plane, in the car, or on the Amtrak. All of their popcorns are air-popped daily so you can assure they’ll be fresh. I recommend getting the Garrett Mix which has both their signature flavors – caramel crisp and cheese corn.

Enjoy the Architecture of Union Station

The last thing I’ll include in this guide to 24 hours in Chicago is a visit to Union Station. This is where you can take the Amtrak if you’ve traveled by train but even if you didn’t it’s worth a visit to see this iconic building. Union Station originally opened in 1925 after years of planning and preparation. It is considered to be the 3rd busiest train station within the United States averaging at 300 trains per day.

What do you recommend visiting in 24 hours in Chicago?