The Windy City: 24 Hours in Chicago

Only 24 hours in Chicago you say? I know, after returning from Japan you’d think we’d be ready to stay home and take a break from our travels. However, Logan had surprised me with tickets on our anniversary to see Lady Gaga & Tony Bennett in Chicago a few days after our return. Yeah, we might be crazy! So we 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.


You can imagine how crazy this 36-acre lawn and parking are was for the concert

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

The next morning we had a little less than 12 hours to enjoy as much as we could in Chicago so we headed towards the downtown area.

Here are some of the top things to do with 24 hours in Chicago

Visit Millennium Park

Cloud Gate “The Bean”

Enjoy Chicago-style deep dish pizza


As it was Logan’s first time in Chicago I HAD to take him to a pizza joint for some Chicago-style deep dish. We decided on visiting Lou Malnati’s Pizzeria.

Visit the Art Institute of Chicago Museum

Home to some of the most well-known paintings including this Van Gogh.

Grab a snack for the road at Garrett’s Popcorn

Photo credit: Garrett’s Popcorn

Enjoy the architecture of Union Station

What do you recommend in Chi-town?

How to make the most out of 24 hours in Chicago.

  • Sarah R
    December 29, 2016 at 8:06 PM

    24 hours seems like such a crazy short time to experience Chicago! Props to you for getting so much done.

  • Liliane Fawzy
    April 16, 2017 at 10:49 AM

    I’d really recommend the Planetarium! It was so cool. But I definitely agree with Millenium Park!