32 hours in Chicago – May 21, 2026

I’ve always really liked Chicago. When I drove across the country to move to Connecticut back in 1989, I stopped there for three days and told my dad that if Connecticut didn’t work out, I was going to give Chicago a try. I STILL think about moving there every once in a while, and then I remember the winters they have! LOL!

So imagine my delight when my schedule came out for May and I had a trip to Chicago with a 32 hour layover! Jeff was planning to join me, and the hotel was rumored to be excellent, so I was VERY excited.

The morning before the trip there were plenty of seats and Jeff and I were psyched for a mini-getaway. But then the East Coast was hit with major thunderstorms that evening resulting in many cancellations. So much for any empty seats for Jeff. Sigh. Oh well. There would be other opportunities for the two of us to go. In the meantime, my trip was still on!

The hotel was every bit as nice as people said, with plenty of old-fashioned touches from when it was built. It was also conveniently located in the heart of downtown, with my first destination – the Art Institute of Chicago – only a few blocks away.

I’m not a huge art museum person, but I’m trying to develop more of an appreciation for it. This was a great museum to work on that. I downloaded their app and decided to take the “Ferris Bueller” tour.

For those of you who haven’t seen this 80’s classic movie, Ferris, Cameron, and Sloans skip school for the day and have a variety of adventures in Chicago. One of the things they did was to go to the Art Institute. It’s actually one of the best scenes in a movie filled with them. Ferris and his friends look at a dozen or so art pieces, and it’s accompanied by excellent music – an instrumental cover of The Smiths’ “Please, Please, Please Let Me Get What I Want” by The Dream Academy.

Well, I’m obviously not the only one who loves the scene in that movie because the app has a specific tour guiding you to all of the pieces that were featured in the movie. I had a very enjoyable time them all down with the music playing through my head, ear worm-like. I also checked out some classics like “American Gothic” by Grant Wood and “Nighthawks” by Edward Hopper. Nighthawks in particular was SO much better in real life. It was as if the painting glowed from within.

I rounded a corner, glanced up, and stopped in my tracks. A copy of this painting hung in my grandparent’s house when I was a child, and I was instantly transported back 45 years with all of the feels. Art doing its thing!

Maybe it’s the way the museum displays its works, maybe it’s because I’m getting older, but I thoroughly enjoyed my visit and came away with a desire to visit more. So I’d say it was a rousing success!

After getting some culture I made an obligatory stop for a picture of The Bean.

Bean selfie!

Then, I walked over to Navy Pier and enjoyed the lakefront for several hours. There are SO many more things I would have liked to see, but I keep reminding myself that I can’t do everything in a day so I try to pick just a few in each stop and save the rest for another time.

You can’t keep the sailor away from the water! Navy Pier in the distance.
Chicago has such a great skyline.

All in all it was a GREAT layover, and I definitely would like to bid for this specific rotation again once the summer is over. Since Chicago is prone to thunderstorms in the summer which results in delays and cancellations at O’Hare, I’m going to stay away until the fall! But I’ll absolutely be back.

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