Chicago winter trip with kids

We went to Chicago with our kids in the winter time. Sounds crazy to visit the windy city at this time but my husband had a conference there so we tagged along. I knew I wanted to eat deep dish pizza and go up the Willis Tower. Other than that I wasn’t sure what Chicago had to offer. It turns out there are a lot of things to do there. We were there for three full days. The first two days I did by myself with the kids and the last day Matt was able to join us.

Chicago Winter Kids

Here’s the quick version

Day One:

1) Jelly Belly Factory Tour- Wisconsin

2) Long Grove Illinois- The Village Tavern

3) LDS Temple

Day Two:

1) Museum of Science and Industry

2) Giodanos Deep Dish Pizza

3) German Christmas Market/ The Bean/ Millenium Park

Day Three

1) The Art Institute of Chicago

2) Willis Tower

3) Gino’s East

The Long Version

 Day One Chicago

We stayed at the Marriot Marquis. We stayed here because it was close to my husband’s conference. Because we didn’t stay downtown we spent a fair amount on parking (almost $90 one day!). Should we have done Uber with a request for four carseats? I don’t know and didn’t even try. I definitely think there are advantages to staying downtown when it’s warmer so you can just walk every where.

I’ve never been to Wisconsin and it’s close to Chicago so we went there the first day. You can read more about our experience with the Jelly Belly factory here. My dad lived in a suburb of Chicago called Long Grove. He said in it’s day it was a big tourist town. Long grove is home to one of the oldest restaurants in America. He worked at that restaurant and it’s called the Village Tavern. It has a beautiful mahogany bar. The staff was friendly and we had a quiet meal at the restaurant and saw his old home. My dad said that he remembers shoveling snow off the roof of his home. I can’t imagine how much snow must accumulate each winter. As we drove back into the city we stopped to look at the Chicago LDS temple.

Since we had a newborn on the trip it took us awhile to get out of the hotel each day. Which was ok because we had an Amazon fire stick. I was getting tricky finding appropriate tv programs for our kids at the hotel. It felt like the only show available was Sponge Bob and I was done with him. I’m so glad we had it. I was able to get everyone ready and feed the baby a few times before we left each morning.

Day Two Chicago

The second day we went to the Museum of Science and Industry. My Saint Louis Science Center Pass is an affiliate with a number of museums across the country. I looked up which ones we could get into for free in Chicago and this was one of them. It was so good. They had underground paid parking on site. It’s always fun to go to science museums and see which exhibits make them unique. My favorite exhibit was the mirror maze. You had to get a free timed ticket – so we got our tickets first and then wandered around the museum. We didn’t pay for any of the extra exhibits and we didn’t have time for them any ways so it worked out. I liked the human body section  as well. It had a fun little quiz to see what exercise is best for you best on your personality. Yep, no surprise swimming, running, low risk, introverted activities for me please.


After we went to the Science Museum we went to the hotel to regroup for dinner. Matt had been to Chicago before and wanted try a deep dish pizza place he had not been to before. He felt like there were four big “chains” the original Uno’s, Lou Malnatis, Giordano’s, and Gino’s East. He had Lou Malnatis the last time he went so we went for Giordano’s. We picked one in downtown so we could walk to Millennium park and a German Christmas market afterwards. Deep dish pizza is very heavy, cheesy and I loved it. Giordano’s was a double decker pizza. I definitely could not eat that every day. My brother in law’s favorite deep dish place was Gino’s East and I could see why- there seemed to be more toppings. We got sausage and pepperoni at both places.

Walking around at night in Chicago was fun. I admired everyone’s long coats and felt like a pro walking around the city with four small children. I used a snow bib from Old Navy for the newborn and was so happy I bought it for the trip.  Ya know if you dress warmly the cold isn’t so bad. But still not brave enough to spend extended periods of time like to see the lights at the Lincoln Park Zoo. Giordanos Deep Dish Pizza Chicago

Day Three Chicago

Our last day we went to the Chicago Art Institute. I was on the fence if we should go here but so glad we did. There were a couple of famous paintings that I knew and honestly thought we could be in and out of the museum in 20 minutes (I feel a little uncultured admitting that). We our Bank of America cardholders and the first weekend of every month there are certain museums that are free for cardholders. We happened to be in Chicago the first weekend of December and the Art Institute is free for children under the age of 14. So in we went. We gave the kids a Map and showed them the famous pieces of art on the back and made it into a scavenger hunt of being in the museum. My son loved the suits of armor and weapons. I don’t think I had seen a toddler/kid sized suit of armor before. The horses had armor on and were rather disturbing to me because I think they were real and they had their tongues hanging out. It actually turned out that there were a lot of famous pieces of art and artists in the museum that I did know and just were advertised. After we got home I searched for best art museums in the world and the Chicago Art Institute made several lists. We spent way more than 20 minutes in the museum. There looked like there might have been a children’s area but we didn’t get there.

Our last stop was the Willis Tower. When we got there we were told there was zero percent visibility. So, would you pay to see nothing? We sure did. I don’t know when we will be back to Chicago and there were a few benefits to going then. We were able to stand on multiple sty decks and not rush our time on the sky deck. We saw a sign that said parties of 4 or less could have 60 seconds on the sky deck and parties greater than 3 could have 90 seconds. What a short amount of time. Between that sign and seeing all the stops and lines to get to the top we could tell the lines could get VERY long. Even though we couldn’t see the ground I still had a bit of anxiety stepping onto the platform. I could see that I was hanging off the side of the building and could see the windows going down the building.

Chicago Art Institute    

I would love to go back to Chicago when the weather is warmer to do an architecture boat tour, walk around Maggie Daley Park and Navy Pier. Visiting the sky deck  when we could freak ourselves out a bit more and see everything. If I’m wishing then I would add Alinea to the list as well. Nevertheless we had a great time visiting the windy city. Have you been to Chicago and if so when did you go and what did you do?


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