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Explore Family Friendly Chicago Like a Native

Make the most of your family trip to Chicago with a native's tips!

As a native Chicagoan and proud Midwestern girl, I say: bravo to you for venturing from the coast – you are in for a treat in Chicago! This third largest American city offers the best of the Midwest along with the excitement, amenities, and attractions of a big city. And it’s a great place to explore with your kids, no matter their age. Hit these areas for a taste of Chicago’s highlights.

The Lake

You may have traveled to the middle of the country, but you’re still along a shore – this time it’s the shore of Lake Michigan. In the summer, head to the beach to enjoy Lake Michigan’s cool waters and beautiful views of Chicago’s skyline. Ohio Street Beach is near downtown and has a fun, energetic vibe. 31st Street Beach is a local’s secret: south of the city, it features a fantastic view and much smaller crowds.

In the winter, you can still get a taste of Chicago’s shoreline by visiting the Museum Campus, which is situated right on the lake. While you’re there, visit one of Chicago’s award-winning museums. The Shedd Aquarium showcases animals native to Lake Michigan as well as oceanic creatures, and the dolphin shows and live diving demonstrations will engage your whole family. At the Field Museum, you can wander among dinosaurs, prehistoric humans, bugs, gems, and more. Finally, the Adler Planetarium has recently been renovated and will be a highlight of the trip for your aspiring astronaut. Be sure to bring your Philadelphia museum membership cards and ask about discounted or free reciprocal admission.

The Loop

It may seem crazy to travel so far just to take a joyride on public transit, but a trip around Chicago’s famous Loop is a fun way to get a view of downtown. Most of Chicago’s trains are elevated (the trains are called The El), so instead of looking at dark subway tunnels you’ll feel like you’re in the middle of Chicago’s tall downtown buildings. Hop on the purple, brown, green, or orange lines and travel around the circle. You can hop off at Adams/Wabash stop to visit the Art Institute or wander the historic State Street shopping district.
The Loop train ride also takes you right to Chicago’s theater district at Washington/Wabash. Chicago hosts many top Broadway hits (including Hamilton!), and tickets can be less expensive and easier to come by. This summer, Monty Python’s Spamalot and Waitress will be in town.

Millennium Park

Chicago’s Millennium Park is a treasure on the downtown lake front. You could spend an entire day in and around Millennium Park gazing at your reflection on Chicago’s famous Cloud Gate Sculpture, affectionately called The Bean; enjoying breathtaking views of Grant Park, Millennium Park, and the Chicago skyline on BP Bridge, designed by Frank Gehry; playing in the water at Crown Fountain, and wandering the 3.5-acre Lurie Garden.
The BP Bridge leads to the Art Institute’s Modern Wing, near Terzo Piano.  Terzo Piano is fancier than you might choose for your kids, but the views are delightful, so consider stopping by for a drink or snack, or even lunch or an early dinner.  The Art Institute’s Family Room is free to visit, and the museum itself was rated the best museum in the world in 2017.
Maggie Daley Park is truly magical.  At its center is the 3-acre Play Garden, a wonderland with six distinct play areas featuring slides, high climbing structures, bridges, towers with fun views of Lake Shore Drive, hills, swings, and more.  A skating ribbon nearby is open year-round: ice skate in the winter and rollerblade or ride a scooter in the spring, summer, and fall. Rentals are available for both. Your family can also go mini-golfing, climb a climbing wall, or play tennis at Maggie Daley.
If you go to Maggie Daley, be aware that it is very big.  Consider dressing your kids in brightly colored shirts and be sure to establish ground rules and meeting places. Take advantage of boundaries offered by the Play Garden’s distinct areas, and move among them together.

Michigan Avenue

If your kids are like mine, taking them shopping is not fun for anyone. But, Chicago’s Mag Mile is famous and worth a peek, and there are kid-friendly things to do nearby. At Water Tower Place, you can visit Chicago’s American Girl Store and experience Food Life, a fun, upscale food court where kids will have fun using their “credit card” to buy their food.
Next, head next door to Chicago 360 in the John Hancock Building. Interactive exhibits provide lots of information about the buildings you’ll see, and if you want a thrill, try the Tilt ride! If you’re ready for a cocktail, go instead to The Signature Lounge on the Hancock’s 96th floor and grab a drink and snack near a window. (Note the dress code.)

The River

The Chicago River, which connects the city via the St. Lawrence Seaway to the Atlantic Ocean, is what made Chicago grow into a powerful city. It runs right through downtown and beyond. The city has recently focused on cleaning it up, and the riverfront path is now a lovely place to stroll. Visit the Chicago River Museum to see how the bridges over the river work and learn about the river’s role in the city’s history.
If your kids are older, a Chicago Architecture Foundation River Cruise is a must! You’ll learn all about Chicago’s architecture and also experience a water lock when your boat moves onto Lake Michigan from the river.
The architectural tour is best for kids age 8 and up, so if yours are younger, consider a ride on the Chicago Water Taxi if you’re visiting in the summer. It gives you the same fun traveling in a boat on the river, but with a shorter duration and without the narration. To make your water taxi ride into a real outing, travel from downtown to Chinatown and hop off to play in Ping Tom Memorial Park, and find dim sum or a sweet treat in Chinatown Square.

Hyde Park

Located seven miles south of downtown, is Hyde Park– home to the Obama family, the University of Chicago, and the Museum of Science and Industry. No destinations related to the Obamas are yet available, but in the future you can come back to visit the Obama Presidential Center. For a taste of the University, head to 59th Street to eat or wander the campus.
The Museum of Science and Industry is a unique, knock-your-socks-off, 400,000-square foot museum that’s well worth the trip to Hyde Park.  The museum is a quick drive down Lake Shore Drive and has a parking lot (and is also accessible by bus from Michigan Avenue). Even after a lifetime of visiting the Museum of Science and Industry, I am delighted to go back to visit favorite exhibits like the Great Train Story, a huge model railway that can whisk you across the country; an actual airplane suspended from the museum’s in the Transportation Gallery; Colleen Moore’s Fairy Castle; Yesterday’s Main Street depicting Chicago at the turn of the 20th century complete with an old time ice cream parlor; the baby chicks that are now located within the genetics exhibit; the coal mine; Toymaker 3000; the U505 submarine…..you get the idea. Even the building itself is something to see– it was built for the 1893 Columbian Exhibition and opened as a museum during 1933’s Century of Progress World’s Fair.

Lincoln Park

Head north of downtown to visit one of America’s largest urban parks and a more residential area of Chicago. If you can, go on a Saturday morning and start at the Green City Market. You may run into a famous Chicago chef, and you’ll definitely run into delicious local produce and favorite local treats.
Just across the street from the market on the east side of Lincoln Park, Chicago’s Lincoln Park Zoo is free to enter.  Enter near the Farm in the Zoo, and then wander through other exhibits according to your interest.  You can then exit south and visit the Nature Boardwalk, a restored natural area home to turtles and fish or north toward the Alfred Caldwell Lily Pool and Lincoln Park Conservatory and Garden.
Chicago’s lakefront path is a centerpiece of Lincoln Park.  Rent bikes or just enjoy a stroll.


Baseball emotions run high in Chicago, so at the risk of making this article biased, I recommend heading to Wrigleyville during your visit.  Wrigley Field is home of the Chicago Cubs and is one of the most historic, iconic ball parks in America.  It is unique because it’s located within a residential neighborhood (Wrigleyville).  If you can get tickets, do so, but even if the Cubs are not in town or it’s off-season, wander the perimeter of Wrigley Field to see the famous statues and the ivy-covered walls.  Especially if you go on a game day, do like the locals and take the Red Line to Addison.
You can also catch the Chicago White Sox at Guaranteed Rate Park on the Southside.

Chicago FAQs


  • Do I need a car? While Chicago’s public transit is good, it is much more car friendly than New York and some places (like the Museum of Science and Industry) are more easily reached by car. However, if you stay near downtown you can do most everything on public transit and taxis also abound. Plus, parking a car at your hotel will be expensive.


  • Where should we stay? To see the sights on this list, staying in the Loop or River North would be best. Downtown is also where the public transit bus and train lines converge, so it will be easiest to get places from here.


  • When should we go? What you’ve heard about Chicago’s winters is true – they are cold. However, the city is truly magical around the holiday season (don’t miss the CTA’s holiday train) and there are hotel deals to be had in the winter. Chicagoans will tell you that they bear the winter to get rewarded in the summer. While it can get hot and humid, the lake breeze blows and the city comes alive when the weather is warm (between late April and early October.)


  • Where is the best pizza? Chicago pizza is worth the hype, and you should have some while you’re there! Our family’s favorites are Lou Malnati’s and also Pequod’s, which is a less famous spot located north of downtown. Uno’s and Due’s are the most famous spots, and are located on the same corner, so you can choose the spot that has the shortest wait. Know that the wait time (after ordering)– a Chicago pizza is long so don’t bring your kids starving.

Photographs by Rachel Kramer.

Contributing Writer