Travel, Travel Guides

Things To Do in Chicago

We spent a few days in Chicago in March 2019 and loved our time there. The weather was a tad cold (and windy), but the crowd level was perfect. I was 5 months pregnant and this trip was so easy being pregnant. Here is our guide on Things To Do in Chicago.


If you want to travel on a budget- go places during the off season when hotels are cheaper and often attractions are lower in price as well. We use Priceline or Hotwire to check for cheaper hotels. We also will check Airbnb, but in some cases a hotel is just cheaper.

Things To Do in Chicago:

Here are the things we did to fill our days (and a few that were recommended that we didn’t get to)
-Explore Millennium Park (this is the park with the bean)
-Visit The Bean both day and night (or in our case, every time we walked by it).

– Go to the top of the Willis Tower. Buy your tickets ahead of time and get the iconic picture in the glass box. We visited at the perfect time because there was hardly anyone there and we could take our time.

– Catch a show. We saw Hamilton (again) and loved the Chicago cast so much. Dear Evan Hansen was also in town when we visited. Hamilton was a lot cheaper than other places because of the time of year we went
– Get deep dish pizza. It wouldn’t be a trip to Chicago without trying the iconic classic. We chose Lou Malnati’s over Giordanos because it had better reviews online, but you can’t go wrong trying both!
– Get a Firecakes Donut Ice Cream Sandwhich
– Walk around the city at night
– Take a Walk on Magnificent Mile. A beautiful mile (or longer?) stretch of some of the most beautiful buildings and fun shopping.
– If you are into art museums, the Art Institute of Chicago is wonderful. We had fun perusing soo much art and learned so much.

-Visit the Shedd Aquarium. The aquarium was so fun and full of the cutest animals. We loved it
– Visit the Field Museum. We learned a ton at this museum as well and got to see a seasonal mummy exhibit which was awesome.
– Take the elevator up to the Signature Lounge in the John Hancock Building. We explored around for the beautiful views and skipped the beverages. If you are female, make sure to check out the bathroom for some of the most incredible views of the city.
-Architecture River Cruise, we didn’t do this because it was too early in the season, but it was recommended over and over again. *
– Visit Navy Pier
– Lincoln Park Zoo (its free!)*
– Visit the Chicago Theatre
– Take a Mob Tour (we ran out of time and did not get to do this sadly)*
– Eat a Chicago Style Hot Dog
– Eat Garretts Popcorn
– Visit Wrigley Field*
– If you played with American Girl dolls as a child, visit their Flagship store

Overall, we loved Chicago! It was such an easy city to navigate and there were soo many things to do. I was 5 months pregnant during our trip and never felt limited. We spent 4 days and it was the perfect amount of time. We also stayed super central to most everything so we could easily walk and took Uber and Lyft when things were a tad too far.

*Things we did not personally do because they were closed or we ran out of time

We hope you enjoyed our guide on things to do in Chicago. Here are a few more guides from our other trips!
Do you like travel guides? Below are some of our others!
>>Banff National Park
>>Niagara Falls


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  • Reply Mamithinks

    Chicago is definitely on our list!!! Willis Tower for sure! Thanks for sharing!!

    June 10, 2020 at 2:07 pm
    • Reply thepriceadventure

      It is such a fun city! We are obsessed!!

      June 13, 2020 at 1:17 am

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