Discover the Best Destinations in Chicago

There are so many nice activities to do with kids throughout Chicago that it can be difficult to decide! Here is our list of the things to do when visiting Chicago to kids and parents, as well as restaurant and lodging recommendations. There are many activities in Chicago, ranging from museums on the Chicago Lakefront to a food tour and the Ledge.


Details on our favourite Chicago attractions can be below! There is so much to do in this city that it is difficult to decide what you will do. Consider the Go Chicago Explorer Pass or the Chicago City Pass.

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1. Navy Pier

Do you want to go walking and sightseeing? Walk out onto the pier and through Navy Pier’s restaurants and shops. It is only free if no purchases are made:). And they do have some interesting activities and attractions, so spending some money here may be worthwhile. 

Looking for ways to get around town with kids? Check out this fantastic post on how to use Lyft and Uber with kids! If you want to see more of Chicago, don’t forget to stop by the South Side! This article does an excellent job of highlighting the must-see attractions on Chicago’s South Side.

2. Millennium Park

It’s a bean-shaped thing in the middle of a park… and then we found it. It’s actually cool! You can look at it 20 different ways and see a different reflection each time because of its shape and reflection. We had a great time exploring all of the different angles and going beneath them. 

Did you know it’s called the Cloud Gate instead of the Bean? If you happen to be in Chicago, users should absolutely pay it a visit. It is in Millennium Park. If we had been in town for a longer period of time, we would have spent a day at Millennium Park.

The land of Chicago is a fantastic place for your vacation so book a cheap flight ticket to Chicago and spend your days here!

3. Gino’s East Pizza

I grew up in Wisconsin, but I don’t recall ever having true Chicago deep dish pizza. Yes, I’ve had Uno chain pizza, but it pales in comparison to true deep dish pizza in Chicago! We went to Gino’s East (South Loop location) and sat in a booth with a view of Chicago’s streets. 

They also have a brewery, so we were able to enjoy delicious pizza and microbrews! It’s difficult to say which was superior because I preferred Gino’s crust but preferred Giordano’s sauce. But, in any case, both were excellent, and I would return to both. One of the best things to do in Chicago with kids is to visit all of the deep-dish pizza joints!

4. Best Western River North

The Best Western River North is another nice hotel option. This is a great hotel if you’re looking for a more affordable option with a large room. It’s also in a great location for walking to many of the downtown attractions. Our room was enormous, with two double beds and a pullout bed. 

They also have a large pool, which was ideal for our family and allowed the kids to get some exercise. Another plus was their on-site restaurant, which served pizza for dinner, had a bar, and had a great breakfast menu. It was snowing when we were there, so it was convenient that we didn’t have to leave the hotel to get a tasty and convenient dinner and breakfast.

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5. The Guesthouse Hotel

I’m not even sure if it’s appropriate to call this a hotel! When we walked into the room, we couldn’t believe the high ceilings, space, and beautiful decorations! The owners had begun construction on condos before deciding to convert to a hotel. And we are the fortunate recipients of these incredible hotel rooms! 

We stayed in a three-bedroom suite with two bathrooms (one of which doubled as a sauna!), It was difficult to leave to go exploring when the location was so wonderful!

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