Chicago is practically tailor-made for family getaways, offering a wealth of interactive museums, fabulous parks and jaw-dropping architecture without the aloof attitude or supersized footprint that make some big cities feel like no-fly zones for tiny tourists. From tots to teens, there’s something for every child in the Windy City.

Skydeck at the Willis Tower gives brave little ones a birds-eye view of Chicago © Scott Olson / Getty Images

Scale scrapers and set sail

An up-close encounter with Chicago’s legendary architecture is a don’t-miss for visitors of all ages. Wee daredevils will delight in the city’s pair of high-altitude viewing decks, 360 Chicago at the John Hancock Building and Skydeck at the Willis Tower. As if the observatories’ heights weren’t dizzying enough (they’re perched on the 94th and 103rd floors of their respective buildings), glassy viewing alcoves reward brave little ones with the sensation of being suspended over the city. Not sure which to pick? Skydeck scores points for sheer loftiness, while lakeside 360 Chicago has the edge in the panorama department.

For a ground-up view of the skyline and a boat ride to boot, treat tweens and teens to the Chicago Architecture Foundation’s river tour, which delivers an overview of the city center’s most important buildings from aboard a double-decker cruiser. If your child is too young to know her Burnham from her van der Rohe, forego the formal tour and hop the Shoreline Water Taxi; in addition to serving up spectacular lakefront scenery, the service links two of the most popular ports of call for visiting families: Navy Pier and the Museum Campus.

The Art Institute’s stone lions are a picture-perfect Chicago landmark © Amanda Hall / robertharding / Getty Images

Make art and meet prehistoric beasts

The sprawling Field Museum captures little imaginations with colossal dino fossils (though beloved resident T. rex Sue is off display until 2019), but for an interactive experience to suit a broad range of ages and interests, it’s hard to top the Museum of Science and Industry. Big kids will get a kick out of descending into a coal mine, transmitting secret messages in the whispering gallery, and playing astronaut at the Henry Crown Space Center, while little ones will love peeping at the adorable hatchery chicks and catching their reflections in the mirror maze.

Over at the Art Institute of Chicago – free for under-14s – a real-life audience with some of the most recognizable paintings in the Western canon (think American Gothic, Nighthawks, and A Sunday on La Grande Jatte) may stir your child’s inner Picasso. Dollhouse fans will be enchanted by the tiny universe of the Thorne Miniature Rooms. The whole family can bust out the brushes at the drop-in Artist’s Studio, open daily. And even the most jaded teen will crack a smile for selfies with the iconic stone lions that stand sentry on the museum’s front steps.

If you’re after a quick diversion, the city has a number of special-interest museums perfect for keeping older kids engaged for an hour or two. At the Chicago Sports Museum, budding athletes can face off against virtual reality versions of local legends like Scottie Pippen and Patrick Kane, while the stacks of cash on display at the Federal Reserve’s Money Museum may inspire allowance renegotiations.

Lincoln Park Zoo’s otherworldly pavilion makes a great backdrop for family photos © Jacob Karmel / Shutterstock

Go wild

Wildlife enthusiasts are in for a treat at Lincoln Park Zoo, where Japanese macaques chill in hot springs. With its relaxed pace, the adjacent Farm-in-the-Zoo is geared to the littlest visitors. Be sure to stroll the boardwalk that links the two, where you’ll find an otherworldly honeycomb-like pavilion that makes the ultimate Chicago family photo op. Perhaps best of all for parents, the whole experience is free – even parking, if you’re lucky (or patient) enough to score a spot on Stockton Drive, just steps from one of the zoo’s main entrances.

Just up the street, the Peggy Notebaert Nature Museum earns high marks with youngsters for its butterfly haven, a light-filled indoor garden that’s home to 1,000 winged beauties. And in the South Loop, the Shedd Aquarium makes a splash with scuttling penguins, a shark-patrolled reef and stingrays and sea stars.

Rope bridges and climbing walls beckon at Maggie Daley Park © f11photo / Shutterstock

Park it

When the kids are looking to let loose, Chicago’s at the ready with miles of lakefront and a plethora of parks. With its vertiginous crow’s nests, climbing wall and wintertime skating ribbon, the Loop’s Maggie Daley Park is a crown jewel in the city’s park system, though parents of tiny tots should note that an abundance of boisterous big kids and hiding spots can make it a bit nerve-jangling. The wide-open spaces of nearby Grant Park, best known for pretty Buckingham Fountain, may be a better match for small ones. The AT&T Plaza at Millennium Park, home to super-photogenic interactive sculpture Cloud Gate (or the ‘Bean’), is a winner with kids of all ages.

Come summer, more than two dozen lifeguard-manned beaches beckon. Tucked behind the Museum Campus, 12th Street Beach gets props for its manageable size, proximity to the Loop and cool view of the Adler Planetarium. At North Avenue Beach, gutsy teens can test their balance on a stand-up paddleboard.

When the weather tanks, Garfield Park Conservatory offers a year-round burst of balmy air and verdant greenery. Inside, a dedicated children’s garden and a range of free drop-in classes get kids pumped about nature.

Summertime brings family-friendly concerts to Millennium Park’s Pritzker Pavilion ©
masmithers /
CC BY 2.0

Catch a beat

It’s never too early for youngsters to get their first taste of the Chicago blues. While most venues cater to the 21-and-up crowd, celebrated club Buddy Guy’s Legends is open to all until 8pm. During lunch and dinner most days, performers play acoustic sets suitable for tender little ears.

On Monday and Thursday evenings during the warmer months, wagon-toting families descend upon the Pritzker Pavilion lawn for the Millennium Park Summer Music Series, a program of free gigs that draws acts like Jose Gonzalez and Femi Kuti. No matter the headliner, the vibe on the grass is chilled-out and super kid-friendly; parents sip wine on picnic blankets while little ones bop and twirl.

Kids with adventurous palates will love digging into dumplings and dim sum in Chinatown © Marco Bicci / Shutterstock

Chow down

Just about all but the most exclusive restaurants will accommodate children without batting an eye, though for your family’s own comfort you might find it best to have your doggie bags in hand by 6:30, when dinner crowds can make maneuvering strollers and highchairs awkward. Adventurous eaters will love slurping noodles beneath the pagodas of Chinatown and digging into enormous dosas amidst the sari shops and Indian candy stores of Devon Avenue: both ’hoods offer a spoil of dining spots that are casual and easy on the wallet.

Certain restaurants go the extra mile to welcome little guests. Lincoln Park’s retro RJ Grunts soothes post-zoo fatigue with kid-sized shakes and burgers along with a complimentary stroller valet, while over in hip Ukrainian Village, Quad Cities-style pizza spot Roots encourages tiny diners to play with their food, distributing dough balls to be squashed and stretched while dinner’s in the oven. (Grown-up topping options like duck sausage and a lengthy Midwestern beer list will keep Mom and Dad happy, too.)

Kids get the royal treatment each afternoon at the Drake Hotel’s Little Prince and Princess Tea, an elaborate spread of dainty nibbles served up in the hotel’s grand Palm Court. Fanciful decorations and carolers make holiday season visits here particularly magical. Parents and rugrats alike will be sweet on the inventive gelato at West Town’s Black Dog and the rich hot chocolate at Logan Square’s Katherine Anne Confections.

The James Hotel offers complimentary amenities like cookies and milk, kid-friendly books and board games © James Hotel

Set up camp

Home-sharing sites offer rental apartments scattered around Chicago’s vibrant neighborhoods. If self-catering’s not your family’s thing, you’ll find a bevy of boutique hotel options, as well as all the usual chain suspects, clustered around the Loop, Streeterville and River North neighborhoods – all good bases in terms of proximity to many of the city’s top kid-centric attractions.

Some hotels make a point of rolling out the red carpet for little ones. The stylish James sweetens the deal with perks like books, board games, and a milk and cookie turndown service. Up in quirky-cool Andersonville, the lovely Guesthouse Hotel offers spacious kitchen-equipped suites and a thoughtful menu of free-to-use kid essentials that run the gamut from car seats to sippy cups.

Getting around

Taxis and ride-sharing services are readily available, but rather than scrambling to stash strollers and secure child seats in an unfamiliar vehicle, consider the CTA train (or El, as it’s known locally). Most major sights are within an easy walk from an elevator-equipped station (indicated on system maps by an accessible icon). Tickets can be purchased at station kiosks. Bear in mind that train car interiors resemble sardine cans during morning and evening rush periods (roughly 6:30-9:30am and 3-6pm); for a comfortable ride, avoid traveling during these times.

Attractions tend to be quietest first thing in the morning. Some spots, like the Shedd Aquarium and the Field Museum, have designated stroller and wheelchair entrances, where lines are often significantly shorter. Finally, if you plan to hit more than a couple of signature attractions, consider a CityPass, valid for admission to your choice of five out of seven major sights. In addition to saving your brood a few bucks, it also includes fast-track entry to spots like Skydeck – no small thing when little legs grow tired and crankiness looms.

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