Chicago is a kid’s kind of town, especially in summer. Take it from this lifelong Chicagoan, mother and auntie: Even the youngest in your brood won’t get bored here. From the lakefront beaches and bike paths framed by a soaring skyline to world-class museums and theaters, Chicago offers abundant family-friendly fun. Here’s a three-day itinerary with kid-approved favorites for first-time visitors.
DAY ONE
Wake up refreshed at your hotel, ideally situated in Chicago’s vibrant River North neighborhood. A hotel like Embassy Suites by Hilton Chicago Downtown River North provides a central base to popular attractions while giving your family space to spread out.
After breakfast, hop on Chicago’s famous elevated train, known as the “L” to locals, to Willis Tower; at 110 stories, it’s the tallest building in the city. Kids will love the short train journey, which rumbles over the Chicago River and slices through the towering buildings of Chicago’s Loop District. At Willis Tower, take the elevator up more than 1,300 feet to Skydeck Chicago for views of up to 50 miles into four states. Daredevils can bravely step out onto The Ledge, a glass-enclosed box that dangles over the streets below.
Descending back to street level, board a Shoreline Water Taxi for an architecturally stunning journey down the Chicago River to Navy Pier. Prepare for excited squeals as your water taxi pulls up to this colorful lakefront treasure boasting shops, eateries and attractions such the Centennial Wheel, with gondolas that offer 360-degree views of the Chicago skyline and Lake Michigan.
While at Navy Pier, grab lunch at Giordano’s to feast on one of Chicago’s best-known delicacies: deep-dish pizza or stuffed pizza. The latter has a cheese-stuffed crust and is topped with chunky tomato sauce. More carnival-style rides, speed boat cruises, tall ship tours and the Chicago Children’s Museum are some of the other diversions at Navy Pier.
For dinner, head to Sugar Factory to feast on rainbow sliders and indulge in one of the restaurant’s “insane milkshakes” (think massive lollipops, cookies, candy bars and sprinkles as tasty adornments). Afterward, head to the Chicago Riverwalk to burn off the inevitable sugar rush. The pedestrian-friendly setting known as “Chicago’s second waterfront” features summertime programming like music, dance and art installations amid a twinkling city backdrop.
DAY TWO
Load up on a proper breakfast at modern-day Chicago institution Yolk. The cheerful setting serves up, most notably, massive portions of fluffy pancakes and tasty omelets.
Work off that big breakfast by wandering down to Millennium Park, home to Anish Kapoor’s celebrated Cloud Gate, better known as “The Bean.” The sculpture is a must-visit for a family selfie with the city skyline reflected on its silvery, silky surface. Millennium Park’s Crown Fountain features two towering digital video displays feature images of Chicagoans “spitting” into a shallow pool perfect for splish-splashing. You might even find time to hit up Maggie Daley Park, a whimsical playground within Millennium Park that includes a three-acre play area in the spirit of Alice in Wonderland and Charlie and the Chocolate Factory, offering things like a giant pirate ship and an “enchanted forest” to explore.
Next, make your way to the Museum Campus, which features The Field Museum of Natural History (dinosaurs!), The Adler Planetarium (space exploration!) and The Shedd Aquarium (ocean creatures!). Don’t try to do them all in the same day. If you opt for The Shedd, which is home to more than 32,000 aquatic animals in a spectacularly designed setting that overlooks the blue waters of Lake Michigan, book one of its Extraordinary Experiences for an up-close lesson and encounter with sea otters, penguins, sharks or beluga whales. Worth the extra cost, it’s an experience that your kids will brag about for years.
After an early dinner, see a show in The Chicago Theater District, which always features family-friendly musicals among its seasonal offerings (think Wicked or Hamilton).
DAY THREE
After two action-packed days exploring Chicago, you deserve to sleep in a little. Maybe. If you still have vacation adrenaline pumping, you could use the first part of the day to go one of two routes: shopping or sporting.
For shoppers: Head to the northern stretch of Michigan Avenue, better known as the Magnificent Mile, for the city’s premier shopping. If you have kids who love American Girl dolls, American Girl Place is a must. Be prepared to splurge on dolls and doll clothing at this two-story wonderland. There’s also an on-site salon and café where kids and their dolls can get styled and enjoy a feast together. Make those reservations well in advance.
For sports enthusiasts: Head to the colorful neighborhood of Wrigleyville for a young slugger’s dream tour of legendary Wrigley Field. On non-game days, the 90-minute guided tours of this iconic ballpark might consist of visits to the seating bowl, press box, bleachers, player clubhouses and Cubs’ dugout—and might even include a chance to step onto the field. These tours are wildly popular, so secure tickets in advance.
Spend the latter part of your afternoon—or perhaps the entire day—enjoying Chicago’s beaches and the 18-mile paved path that hugs Lake Michigan. Rent bikes to pedal alongside the runners, rollerbladers and pedestrians who share this scenic path. For those who simply want to lounge, spread your beach towel at Oak Street Beach, a lesser-known but family-friendly spot at the intersection of North Michigan Avenue and Lake Shore Drive .
For dinner, head to Portillo’s, a local quick-service restaurant chain beloved for its Chicago street food: hot dogs, Italian beef sandwiches, chopped salad and cheese fries. (The succulent chocolate cake here is not to be missed.) End the night by returning to Navy Pier. In summer months, it hosts free fireworks every Wednesday and Saturday night. You’ll conclude your Chicago trip with a full belly, wide-eyed wonder—and a desire to return. (Maybe next time without the kids—wink-wink.)
