Plan a Chicago Trip: Travel Thursday

This Guide to Plan a Chicago Trip is part of our Summer Series: Travel Thursday

As I shared yesterday, during the summer of 2016 Ann Arbor with Kids will be featuring a different post series each week. Travel Thursday will highlight some of our trips as well as planning tips for future trips.

On our family’s travel list for summer 2016 is a trip to Chicago. We went to Chicago in summer 2010 when my daughter was 4. She doesn’t remember the trip, so we figure it is time to return. We did take a day trip in summer 2012 for the American Girl store, but we didn’t tour anything besides the mall.

Chicago Trip Planning

Recently, I have seen some resources for visiting Chicago – Free Museum Days, Free Metra train rides, and new activities that I wanted to share with my readers. Thanks to Go West Young Mom (who covers the Western Chicago suburbs) and Little Lake County (who covers Lake County, IL – between Chicago and Milwaukee) for providing me with their links to share.


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Getting to Chicago

Chicago is roughly a four hour drive from Ann Arbor. In theory you can make it in less, until you hit the traffic in the city which seems to be there at any time of day.

On our last trip, we took Amtrak. The train trip is longer than the drive (roughly 5 hours), and that assumes the train runs on schedule. The plus side of the train is the convenience of not having  a car in the city, especially with the parking fees at most downtown hotels. With a quick look, my family of 3 could travel roundtrip for $166 depending on our train times and dates.

Chicago Trip - on Amtrak


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If you choose to stay outside of the city, you can take the Metra trains into the city. Kids can ride the Metra free this summer with an adult pass including an $8 weekend pass. Get the details from our friends at Go West Young Mom and check out their site if you’ll be staying in the western suburbs of Chicago.

You could also fly, but I don’t think it is worth it from Ann Arbor by the time you factor in transportation between Ann Arbor, downtown Chicago, the airports, and arriving early at the airport.

Museums in Chicago

My family loves to visit museums and Chicago is a great place for museums. We loved the Field Museum and Museum of Science and Industry on our last trip. I can’t wait to take my daughter back to the museums now that she is older and has a better background in science and history.

Chicago Trip - Field Museum - Sue the Dinosaur

Visit Museums for Free This Summer

Museums can get expensive, but there are some affordable ways to visit the museum. Several museums in Chicago offer free days to visit. Our friends at Little Lake County have assembled this guide of Chicago Museum Free Days. If you’ll be in Lake County (between Chicago and Milwaukee), be sure to check out their site for more activity ideas.

However, the best way I have found to visit museums is to use the ASTC Reciprocal benefit from our Ann Arbor Hands-On Museum Membership. You also receive ASTC reciprocal benefits from a membership to the University of Michigan Museum of Natural History. We have visited museums across the country (and in Toronto) for free with these memberships.

Participating ASTC Museums in Chicago:

Even if you are using your ASTC membership, I suggest referring to the Free Days list to avoid the crowds that are present on Free Museum Days.

Free Chicago Activities

Lincoln Park Zoo is a free zoo located just over a mile north of the John Hancock Center. It is easily accessible via bus.

Maggie Daley Park is a relatively new addition to Chicago. It is a downtown park that was opened in December 2014. The park does include a climbing wall and miniature golf that have an admission charge. There is also a skating ribbon for winter that offers free skating if you bring your own skates, or rental skates available for a fee. Check out Little Lake County’s review from spring 2015. The park also hosts free events such as an outdoor movie. They’ll be showing The LEGO Movie on June 26.

On our last trip, we also enjoyed visiting Millennium Park and Buckingham Fountain.

Chicago Trip - Buckingham Fountain

Other Chicago Activities

As I mentioned, we made a day trip to Chicago in 2012 to visit the American Girl Store in Water Tower Place. If you have a daughter who loves American Girl dolls, I definitely suggest scheduling plenty of shopping time (and planning to spend the money you saved above with our free museum tips). As a bonus, the LEGO store is located in the same complex so your LEGO lover can also do some shopping.

Chicago Trip - American Girl Store

The views from the Sky Deck at the top of the Sears Tower (my dad worked in the building when I was a kid, so I’ll never call it the Willis Tower) are amazing. We loved going to the top on our last trip particularly since the weather was nice that day. You can also go to the top of the John Hancock Center.

Chicago Trip - Skydeck at Sears Tower

Other Suggestions

Where to Stay

On our 2010 we stayed at a Hampton Inn. It was newly remodeled, breakfast was included, and WiFi was available. However, it was a block or two from a fire station, so it was a little loud. 

Do you have other suggestions for what to do or where to stay on a Chicago trip? Add them in the comments.

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Anna Mae

Anna Mae owns & operates Ann Arbor with Kids, a website dedicated to Family Activities in Ann Arbor. My husband and I moved to Ann Arbor in 2003 and our daughter joined the family in 2006.

Anna Mae

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