Highlights of a Quick Trip to Chicago

I’ve been to Chicago three times, all for work and every time in December. Cold does not begin to describe a Chicago winter for this Californian. I have memories of locals staring at my earmuffs and probably thinking, “What in the world?” I’m glad I can provide some entertainment for others while I travel.

I didn’t want to subject my two children to further childhood trauma so I decided we’d visit Chicago when it was a little bit warmer, which was much more enjoyable. We spent two days sightseeing. I would have loved to stay longer but you know how that goes.

Here are the highlights of our short but fun stop in Chicago.

What to do in Chicago in Two Days

Museum of Science and Industry
Let’s start with my kids’ favorite stop. I thought it would be just another museum visit, but they loved the Chicago Museum of Science and Industry. We spent about six hours here. Had it not been for dinner reservations, we would have stayed the entire day. Next time.

We couldn’t see or experience something just once. We would watch something two or three times. We spent 30 minutes just watching real chicks hatch from their eggs. The museum has a mix of fixed objects with descriptions and interactive presentations. This was the one place our kids loved, and we will devote more time on our next visit. 

What to do in Chicago with Kids, Chicago Attractions - Museum of Science and Industry
If you’re wondering what to do in Chicago with kids, the Museum of Science and Industry provides hours of interactive fun for the family.

President Obama’s House
While you are at the Museum of Science and Industry, you might as well swing over to President Barack and Michelle Obama’s home in Chicago. No, you won’t be able to go in. At the time, it was gated and guarded by U.S. Secret Service agents. But you can take a picture in front like we did. Also in the neighborhood is the University of Chicago campus, which we drove by hoping to inspire our teenage daughter.

President Barack and Michelle Obama’s house in Chicago:
5046 S. Greenwood Avenue; Chicago, IL 60615

What to do in Chicago with Kids, Chicago Attractions - the Obama's house
Snap a quick pic in front of President Obama’s house in Chicago.

Architectural Boat Tour
An architectural boat tour of Chicago is a relaxing and fun way to see and learn about the history of the Windy City. It was also a good break from all the walking we’d been doing. This 90-minute tour sells out during popular seasons so buy your tickets in advance.

What to do in Chicago with Kids, Chicago Attractions - River tour
An architectural boat tour is a relaxing and educational way to see Chicago

Art Institute of Chicago
One of the great museums of the world, the Art Institute of Chicago houses some of America’s finest art. Unfortunately, we didn’t make it past 90 minutes. My kids got tired and uninterested after only an hour, due to poor planning on my part. Maybe we should have looked for more activities and workshops or spent some time in the family exhibitions. Instead, I wanted to show my kids some of my favorite iconic American portraits. Major fail. I don’t think my kids will be studying art history in the future. As Taylor Swift says, “Shake it off,” and we’re on the the next stop.

What to do in Chicago with Kids, Chicago Attractions - Art Institute of Chicago
See some of America’s great iconic paintings at the Art Institute of Chicago.

Chicago Deep Dish Pizza
On this visit, our friends and local residents took us to Lou Malnati’s. I’ve been to the other classic deep dish pizza restaurants, and Lou’s distinguishes itself with a well-balanced, buttery crust. You cannot visit Chicago for the first time and not get some deep dish pizza. They also serve a thin crust version that the kids liked more, which means I will be taking them back to Chicago for further convincing.

What to do in Chicago with kids, Chicago attractions - Chicago Deep Dish Pizza.
Try the balanced, buttery crust of Chicago deep dish pizza at Lou Malnati’s.

Lessons Learned
One of the highlights for me was revisiting the mathematical observation called the Golden Ratio at the Museum of Science and Industry. It’s found in patterns of nature and said to be incorporated into designs from the Pyramids of Giza to the Mona Lisa to even Apple products.

Since the ratio is aesthetically appealing, as well as widely observed and used, I wondered how the Golden Ratio of 1.618103 could be applied to our family trips. It seems that with every trip, there is a part of the day when someone is unhappy. Too hot. Too cold. Why can’t I buy this? Are we there yet? I don’t like pizza. 

Is there such a thing as a perfect trip? There isn’t. Just as not everything can fit into the perfect aesthetics of the Golden Ratio, not all trips or experiences can be perfect or pleasing to everyone.

Frankly, I was disappointed that we did not have more time to see more things in Chicago and that my kids were not interested in great American portrait paintings. But you know what? Overall, it was a great trip because, quite frankly, there will be a day when we won’t be able to travel with our children. I’m counting my blessings. I’m also coming to terms with the fact that as much as I want trips to be perfect, they never are, and they don’t have to be. Enjoy the time you have together. Happy travels!

You may also enjoy:

Hilton Mom Voyage writers receive free night certificates to use at Hilton Hotels & Resorts worldwide. To learn more, visit our About Us page.

What to do in Chicago with Kids, Best Chicago Attractions for Kids

Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.

This post was written by Hilton Suggests Team Member, Eugene C. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

More posts from Eugene C.