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7 Things Local Families Love About Chicago

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 ride on the hop-on-hop-off bus to the major sights, try a Segway tour, or stroll along Michigan Avenue from the Art Institute passed the 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 activities that we think you might enjoy as well.

6 Chicago Activities Local Kids Love

Play by Lake Michigan

kids play on a lake michigan beach.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.

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.

Dine al Fresco

dining al fresco at piccolo sogno in chicagoOne 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.

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.

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. (Read our review of the Loews Chicago hotel.)

See the city from the water

the chicago skylineSeeing the Windy City from 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 find the right tour for your group. Shoreline Sightseeing runs one 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 view; 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 has culturally rich and diverse neighborhoods that are 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 Pilsen is more your style with its art murals, taquerias, and National Museum of Mexican Art.

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

Discover the 606 trail

taking a break along the 606 trail in chicagoThe 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.

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

The Field Museum-Kids Are A TripAfter you’ve explored the Art Institute of Chicago (named the best museum in the world by Trip Advisor last year), try one of the many other museums in Chicago worth a visit.

History lovers will enjoy the Field Museum. The Adler Planetarium is all about the moon and stars, of course.

The Museum of Science and Industry has amazing hands-on exhibits that bring science to life for kids and parents.

We also love the Chicago History Museum, Shedd Aquarium, and the Peggy Noteabaert Nature Museum. (Read more about these museums in our Tips for seeing Chicago’s top attractions with kids.)

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.

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.
*Go Chicago Card offers discounts of up to 55% on your choice of 25 attractions. 

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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.


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
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