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Chicago Travel With Kids

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I have always thought Chicago to be a cold, dreary place. I have been three times before without the crew and, although I enjoyed myself enormously, I never thought of it as a travel destination for families. But maybe it’s because I have only ever gone in the winter! Chicago in the summer is amazing with so many things to do and see. I recently visited Chicago and traveled with the kids (My husband had to stay home to work) and although we were only there two days we packed in the fun.

Chicago is a city of blues and greens in the summer. Greenery and flowers fill every nook and cranny. The blue sky and blue water of Lake Michigan bounce off the glass buildings giving the downtown a feeling of space and serenity. I believe that every big city while alike in some ways has that certain something that defines it. To me Chicago is defined by its friendliness, lake front parks, and jostling elevated trains. Like any big city, getting around with young kids can be a challenge, but a challenge well worth the reward.

Although the tourist areas of Chicago are very walk-able, you may want to use public transportation or a taxi.
If you have young kids who won’t use a stroller but cannot walk very far, plan on cabs in the magnificent mile area. They are reasonably priced for a large city and the best way to get from the Magnificent Mile to The Bean or Navy Pier for example.

Take a hop on hop off bus- I would recommend the big bus tours. I have taken three different tour buses and found this one to have the best tour guide and consistency with pick up times. You can cover a lot of ground in one day with these buses.

You can take a car into the city. Parking is plentiful if somewhat expensive. Look ahead on apps like Park Whiz or Spot Hero for parking deals.

Top Attractions

The Bean
Its real name is Cloud Gate but don’t ask a cabbie to take you there or you will get blank looks. (I tried on 2 different visits and neither had any idea what I was talking about. I did it the second time just to prove my point!)
This bean-shaped sculpture is reflective and you will return home with a hundred or so pictures of it in your camera roll. You can take so many interesting pictures that it really is free entertainment.



The Bean is in Millennial Park and is a great place to let the kids explore. For an extra fun time visit the Bean on a Tuesday evening and then walk across the courtyard to Pritzker Pavilion to watch a free movie on the lawn. We watched Caddyshack and ate goodies from snack carts and pretended we were locals! I think it was the highlight of the trip for me.


Plan on 30 minutes for photos of every angle imaginable.

Navy Pier-
Navy Pier is a great jumping off point for exploring Chicago. From the pier you can get boat tours and lake cruises including food cruises. (I really recommend the Seadog river and lake cruises.) You can ride the Centennial Wheel (a huge ferries wheel that is prominent in Chicago’s skyline) and visit the Children’s museum.
Don’t forget to stop at Garretts popcorn; your nose will lead the way!

Plan on 2-3 hours

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The Museum of Science and Industry-
My kids and I spent 5 hours here and wished we had more time to spend! This is a top attraction because kids of all ages will find something fun here.I would say this was the highlight of Chicago for my kids.

Our favorites were the German U-boat display featuring a real U-boat and the story of its capture. My boys loved the simulated steering game.
The mirror maze was hysterical! You never knew what was real and what was a reflection. We all spent an hour going in and out!
If you have 4-6 hours spend them here!!




Magnificent Mile-
I hesitate to add this because it’s not something your kids will love. However, every guide book will mention this section of Michigan Ave. There is lots of shopping and a great architectural tour can be taken if your kids are more patient than mine. Check out the water tower that figured into the great Chicago fire.

Here is a great post on a walk around Chicago. Click here

Plan on at least an hour.


This Macy’s was originally a Marshall Fields Department Store in the late 1800s. And much of the original architecture remains. Walk through the store and find your way to the Tiffany ceiling directly over the makeup section. Be sure to visit the Walnut room as well if you want a nice lunch. (You can take a peek inside even if you don’t want lunch.) On the outside of the building look for one of two clocks erected in 1896 and 1902. Apparently women used to use this as a meeting place for their shopping.

Plan on 20 minutes to see the store but more if you want to shop.

Good Eats:

Deep dish pizza-

There are several pizza joints that locals will say are the best, so I couldn’t just pick one. The consensus from Yelp, Trip Advisor, 2 different hotel concierges, and a few people I asked is Giordano’s, Lou Malnati’s, and Pequod’s.

We chose Giordano’s at Navy Pier. We sat out in the beautiful sunshine and ate gooey cheesy pizza. It is very different from my definition of pizza, and the Northeast is pizza heaven. However, I thoroughly enjoyed what my youngest called “pizza casserole.”

Garrett Popcorn-
Your nose truly will guide you here if you are within a block or two of one of their stores.
It’s the caramel corn that you will smell and the caramel corn you will want to shove by the fistful into your mouth. The traditional mix is cheese popcorn and caramel corn together, and this strange combinations really works! I prefer the plain caramel corn, but you can’t make a bad choice.

Little Sheep Mongolian Hot Pot-

This stop requires a drive out of downtown into Chinatown, but if you can swing it, do!

My kids love to eat things that are different for an experience, so we decided to try Little Sheep after seeing a 5 star Yelp review. I loved how customizable it was, so each kid could have a little of something they wanted.  The idea behind hot pot is that you start with a soup (we chose half spicy and half mild) and and then you pick the items you want to cook in that soup. We ordered way too much food and ate our favorite meal in Chicago.





  1. Sandy gourdine
    November 6, 2018 / 7:34 pm

    Enjoyed your blog and we are taking our grandson to enjoy the sites in Chicago, following your suggestions. Do you have a hotel recommendation close to sites you mentioned?

    • travelswiththecrew
      November 6, 2018 / 10:00 pm

      I’m so glad to hear that! You will love the Renaissance Chicago Downtown. It has a great pool and is in easy walking distance to many of the attraction on the Magic Mile. Hope you have a great trip! Let me know how it goes.

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