Chicago with Kids: Favorite Activities

Check out these family favorite activities while in Chicago!

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The Windy City is a fabulous place to travel with kids! It’s an approachable city with good walkability, easy subway (or elevated train transportation) and regular Metra train, as well as plentiful cabs and Uber/Lyft.

There are also so many possibilities for things to do, both indoor and out.

Here, I will highlight just a few of our favorite kid-friendly activities that will make your Chicago visit that much more special.

What to do:

1. Maggie Daley Park

Maggie Daley Park. (337 E Randolph St, Chicago, IL 60601) Adjacent to Chicago’s famous Millenium Park and the photographer’s dream, the Bean, is Maggie Daley Park–an awesome place to spend an afternoon with kids!

This 20-plus-acre park includes the Ribbon (an ice skating path if it’s winter), along with acres of green space, gardens, sculptures and multiple play areas for kids. There are two huge wooden towers that kids of all ages love to explore, nest swings, a huge wooden pirate ship for imaginative play, slides, mirror mazes and much more.

There are picnic tables in a few areas of the park, so it’s a great place to pick up food on your way to the park and have a picnic.

2. Stand Up Paddle Boarding

Stand Up Paddle boarding. If you have school-aged or older children, try Chicago SUP for stand up paddle board rentals that the whole family can enjoy. It’s located at North Avenue Beach in Lincoln Park, just south of the Castaways restaurant. There is a bike path on the beach that will take you right to their little kiosk.

You can rent a paddle board by the hour or go with a group lesson. Depending on your kids’ athletic abilities and confidence in the water, I have found it can be fun to skip the lesson and have everyone learn how to stand up on the board through trial and error.

3. Walk (or Bike)

I do believe setting aside a day or half a day to enjoy Chicago’s Riverwalk as well as Lake Michigan lakefront paths will satisfy the whole family. The Riverwalk path has restaurants as you walk underneath the bridges and Chicago streets, along with a unique view of Chicago’s buildings and architecture.

If your children are tall enough/old enough, you can rent standard size bicycles throughout the city’s DIVY bike program with its pick up/drop off locations scattered about throughout Chicago. It’s inexpensive, easy to use with an app, and a fun way to explore!

The Riverwalk will take you right to the Lakefront path. From there, you and the kids can walk or bike your way to Navy Pier and its famous Ferris Wheel, head to North Avenue Beach or the Lincoln Park Zoo, or go the opposite direction and wind up at Chicago’s Museum Campus (see post on Chicago Museums with kids).

I often find that the seemingly simplistic activities are some that the kids remember the most, such as spending an hour looking at the high Lake Michigan waves crashing against the rock walls or watching the seagulls and other birds hang out on the piers. Bring some picnic food and stay awhile.

4. Afternoon Tea

I love a good afternoon tea. In fact, I try to scout one out in most places we travel to, regardless of city or country.

While there are a number of wonderful places for afternoon tea in Chicago, my favorite when traveling with kids is the Drake Hotel. Afternoon tea at the Drake is not only a regal, beautiful atmosphere, but there is often live piano or harp music to enjoy.

The Drake’s afternoon tea also has a dedicated children’s menu and special high chairs for those little kids that want to bring their favorite stuffed animal or doll to the experience. Unless you want to be disappointed, reservations are a must for this one!

5. Take a Water Taxi

A great alternative for kids too young to stand up paddle board, taking a water taxi is great fun for families of all ages. There are a number of tourist boats that give great tours of the river, skyline and Lake Michigan. Those often include meals or appetizers, drinks and narration.

However, if you just want a convenient, much more inexpensive way to get to the Museum Campus or Navy Pier, that offers the kids a bit of fun, opt for a Chicago Water Taxi. There are plenty of river water taxi options as well. But the Lake Michigan water taxis will take you between Navy Pier and the Museum Campus. They run quite often, usually every 20-30 minutes.

For more Chicago planning, see: