Places To GoUSA Middle

7 Family Activities Chicago Locals Love

Share the Travel Inspiration

At least once a year I book a hotel room in Downtown Chicago—just a few minutes from home—and my husband, kids and I enjoy a staycation. Seeing the city through the eyes of a visitor is one of my favorite ways to spend a weekend.

We’ll do typical Chicago sightseeing activities like riding the hop-on-hop-off bus, try a Segway tour, or stroll along Michigan Avenue from the Art Institute passed Millennium Park to the Water Tower.

While we locals love these major attractions, we have our secrets too. Here are a few of my family’s favorite local things to do in Chicago that you might love as well on a weekend or longer visit.

6 Chicago Things To Do That Local Kids Love

Start with playtime on Lake Michigan

With 26 miles of sandy shoreline, it’s hard to ignore great Lake Michigan on our doorstep.

Chicagoans live for long summer days and spend their free moments soaking up the sunshine and splashing in the water at any of 2 dozen shoreline beaches.

kids play on a lake michigan beach.

For those who don’t love the heat of the day, wait for the fireworks that happen twice a week at Navy Pier and during various festivals throughout the summer.

The beauty of the sparklers over the city and reflecting in lake is magical.

Then Dine al fresco

One of the most enjoyable and kid-friendly ways to experience Chicago’s world-class cuisine is at a rooftop restaurant or an outdoor patio.

The city rooftop views are stellar and dining al fresco brings a festive vibe to any dining experience.

dining al fresco at piccolo sogno in chicago

Some of our favorite spots are the cozy backyards at Piccolo Sogno and Stella Barra pizzeria, and the rooftop at Rock Bottom Brewery.

Many of the downtown hotels also have family friendly rooftop restaurants and bars.

For drinks or a meal with a great view try the terrace at Loews Streeterville Social.

Read more: Our review of the Loews Chicago hotel.

It  welcomes families during the day and early evening and has a grassy area where kids can play (it becomes a bit of a nightlife scene after dark).

Keep in mind kids are often welcome in bars and lounges in the afternoon; less so after 7:00 p.m. or so. 

You must see the city from the water

the chicago skylineSeeing the Windy City from the Chicago River or the lake provides a unique perspective on its buildings and history.

One of the more interesting tours of the city offers a view of its architecture from the river.

Be sure to read reviews and find the right tour for your group. Chicago has famous architecture and plenty of colorful history. Some guides do a better job than others of making it all engaging for kids.

Shoreline Sightseeing runs a tour from Navy Pier that lasts about 75 minutes and covers most of the major points of interest in the city. Children 7 and above will appreciate this tour and the views; younger ones may simply enjoy being on the water.

If you prefer to steer, another option is renting kayaks—on your own or in a tour group— and heading out to explore the lake or river.

It provides a unique perspective on the city and some great photo ops besides.

Explore the diverse neighborhoods

Chicago neighborhoods are culturally rich, diverse and well worth exploring. Head to Andersonville for its Swedish American Museum and stop by the Swedish Bakery for crunchy almond toska tortes.

Or take a tour of Chinatown, stop for dim sum, and enjoy a bubble tea at Joy Yee Noodle.

Maybe once-German and now-Latin-American Pilsen is more your style with its art murals, taquerias, and National Museum of Mexican Art.

Chicago Food Planet offers walking food tours of several Chicago neighborhoods. The tours change seasonally, but usually combine samples of local classics like deep-dish pizza or Chicago dogs with new and interesting additions to the food scene. Most of the tours involve an alcoholic drink or two and will substitute soft drinks for kids, or adults who don’t imbibe. 

Go off the beaten path and explore the neighborhoods, you’ll be surprised by what you find.

Discover the 606 trail

The newest addition to the Chicago trail system is the 606, an elevated trail built on a former freight train line.

This nearly three-mile-long trail connects four neighborhoods, Bucktown, Wicker Park, Logan Square and Humboldt Park.

taking a break along the 606 trail in chicago

The path is 10 feet wide—perfect for walking with a stroller or taking a family bike ride—with a dirt running path on either side.

The trail connects with several city parks and feature several urban art installations as well.

At the western end is an observation deck with great sunset views. The trail just opened this summer and is already pretty busy most weekends.

Sample amazing museums

We love are the Chicago History Museum. Permanent exhibits allow you to trace Chicago’s history and unique culture by riding an L train, visiting a jazz club, “shopping” in Marshall Fields and fitting yourself inside  a Chicago dog.  

Learn about the African America migration north, explore Lincon’s Chicago and see a movie that carries you from the Great Chicago fire to the World’s Fair to the dizzying building of the Sears Tower.  Temporary exhibits might focus on history, social issues, music, fashion and more. 

We also like the Peggy Notebaert Nature Museum, part nature center and part natural history museum. During a visit you might climb around a treehouse, view impressive nature photography, say hello to some lizards or visit the indoor butterfly garden.

There is a lot of fun interactive stuff here to engage the under-7 set. But older school-age kids and younger tweens, especially those interested in science and nature, will find plenty to engage them, too.

I never get tired of exploring the Windy City. There is something magical about the architecture, the water, the sights and the people that makes it a one-of-a-kind city.

Read more: We review the most popular Chicago museums, plus the Shedd Aquarium and Adler Planetarium in
Tips for seeing Chicago’s top attractions with kids.

Planning a trip?
Check reviews and rates for Chicago hotels and activities on *Trip Advisor.
Compare hotel rates with HotelsCombined.
*CityPass  can save you 51% on skip-the-line access to Chicago’s top attractions. 

Pin it for later

7 things to do in Chicago that local families love. Try them all on your next weekend visit with kids. #chicago #thingstodo #kids #locals #vacation #weekendgetaway

Kirsten Maxwell lives in the Chicago suburbs with her husband and three over-scheduled boys. When she’s not working as a substitute teacher, she’s following her passion by writing about travel, including traveling with a child with food allergies. You can find her family travel tips at Kids Are A Trip and or follow her family’s adventures on Facebook and Instagram.


Share the Travel Inspiration

Previous post

6 Ways To See NYC Like a Local Family

Next post

Make Flying Time Quality Time With Kids