Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants, top sports teams, and prized cultural treasures. Called “the Windy City” both for its blustery weather and long-winded politicians, the third largest city in the U.S. has plenty to offer kids and families. See the best of the city in this 3-day itinerary for Chicago created by our Midwest TravelingMom, who calls Chicago home.
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What You’ll See on a 3 Day Itinerary for Chicago
Afternoon Tea at the Drake Hotel
Art Institute of Chicago
Deep Dish Pizza at Pizzeria Uno
Lincoln Park Zoo
Chicago Children’s Theatre
3 Days in Chicago with Kids
Chicago is called the Second City, a reference to its spot as a runner-up to New York City, size-wise. It’s now the third-largest city behind Los Angeles but the famous comedy troupe still embraces the name. However, there’s nothing second rate about this jewel of the Midwest. If you’re lucky enough to have 3 days to spend in this quintessentially American city, you and your kids will discover that Chicago is second to none.
Getting to Chicago
It’s about a 30 minute, $40 cab ride from either of Chicago’s international airports, Midway or O’Hare, to Michigan Avenue. You can also take Chicago’s elevated subway, known as the El, from either Midway or O’Hare Airport to downtown, for just a few bucks per person.
Parking in downtown Chicago is very expensive and public transportation is superb. As a result, you don’t need a car. If you’re on a road trip, you’ll want to park your car outside of the downtown area. If you must drive into the city center, use an app like Spothero to find the most affordable parking spots.
Day 1: Shopping on the Mag Mile, Afternoon Tea at the Drake Hotel and Navy Pier
The stretch of Chicago’s Michigan Avenue north of the Chicago River is nicknamed the Magnificent Mile, or the Mag Mile to locals. This is the Rodeo Drive of the Midwest. There’s plenty of high-end shopping, including some not-to-be-missed Michigan Avenue stops that are kid-friendly. That includes the USA’s very first American Girl store, which is on the bucket list for many young girls visiting Chicago. Alongside the retail store, which sells clothes for dolls and matching outfits for your own child, your daughter’s beloved toy can get dolled up at the salon.
140 E. Walton Place
Chicago has many great lodging options. One good hotel choice is the grande dame of Michigan Avenue, the Drake Hotel. Over the years, this regal hotel has received royal visits from Queen Elizabeth, Princess Diana and the Empress of Japan. Even if you don’t choose to stay there, make it a point to have afternoon tea. It’s legendary.
600 E. Grand Ave.
From Michigan Avenue, hail a cab, order an Uber or, in the summer, jump on the free Navy Pier trolley to travel the one mile east to kid-friendly Navy Pier. The Navy Pier trolley runs every 20-30 minutes from May through September. Home to the Chicago Children’s Museum (one of the best in the country, it’s free on Thursday nights!), the renowned Chicago Shakespeare Theater and a variety of rides, shops, restaurants and fast-food stands, Navy Pier is the Midwest’s No. 1 tourist attraction.
Hop on the Ferris wheel for a bird’s eye view of the Lake Michigan shoreline and city skyline or just take a ride on the carousel. Navy Pier offers events and activities all year round. There are fireworks every Wednesday and Saturday night in the summer. Foul weather doesn’t end the fun. The party moves indoors during December and early January, for Winter WonderFest, which includes ice skating, rides and other attractions.
Day 2: Museum Campus, Buckingham Fountain, Millennium Park and Deep Dish Delights
1400-1562 S. Lake Shore Dr.
Chicago is blessed to have a host of world-class museums. Three of them, the Shedd Aquarium, Adler Planetarium and Field Museum, are connected by green space along the lakefront. You can’t do all three in one day. As a result, you’ll need to pick one. Go with either the Shedd Aquarium or the Field Museum of Natural History. Plan to get there when the museum opens (lines at the Shedd can get really long later in the day) and consider buying a Chicago CityPASS that lets you skip the long entrance lines.
Lunch at Adler Planetarium
1300 S. Lake Shore Dr.
You don’t need to pay museum admission to enjoy a low-cost lunch here with its jaw-dropping view of the Chicago skyline. Kids will love looking through the telescopes at the skyscrapers.
301 S. Columbus Dr.
After lunch, walk a mile along the lakefront path to Buckingham Fountain. In the summer, you’ll welcome the cooling mist as the winds whip the soaring fountains. In the winter, the fountain is dressed with festive lights.
Maggie Daley Park
337 E Randolph St
From Buckingham Fountain, it’s a short walk further north along the lovely lakefront to Maggie Daley Park. This is a kid-friendly urban paradise. In the winter, rent skates to ice skate on the ribbon. In the summer, head up the climbing wall or just play in the nautical-themed playground. Don’t miss a contemplative walk through the Cancer Survivors Garden. Chicago’s favorite first lady, Maggie Daley, in whose honor the park is named, died in 2011 after a 9-year battled with cancer
201 E Randolph St.
This is the stop you’ve been waiting for: the selfie at the Bean! After the kids have run around a bit, walk over to Millennium Park via architect Frank Gehry’s modern marvel, the stainless steel BP bridge. Enjoy a relaxing stroll through the native prairie plantings at the free Lurie Garden. Then head toward Michigan Avenue for a family selfie in the Bean. In summer, Millennium Park is a hive of acivity, including daily free activities for kids and free concerts, movies and more at the gorgeous Frank Gehry-designed stage.
TravelingMom Tip: At the height of summer, be careful the kids don’t touch the shiny tiles along the BP Bridge. They get HOT in the summer sun and can burn little fingers (and big ones too).
If it’s a warm day, pack your kid’s bathing suit. Get ready for squeals of delight as they run among a multi-story video tower near the Bean. It’s the coolest, most remarkable urban waterpark you’ll ever see!
Art Institute of Chicago
111 S. Michigan Ave.
Considered one of America’s best museums, the Art Institute is remarkably kid-friendly. Best known for its impressionist collection, including its masterpiece, Georges Seurat’s “A Sunday on La Grande Jatte,” artists include Picasso, Renoir, and Marc Chagall’s spectacular stained glass windows. The are tours designed for families and a children’s area. But the highlight for kids (and a lot of adults!) is on the lower level. That’s where you’ll find the 68 Thorne Miniature Rooms. One of the Art Institute’s most popular exhibits, here you’ll find the dollhouses of your dreams. Get a glimpse into these painstakingly replicated interiors ranging from 13th Century Europe up to 1930’s America.
Here over the winter holidays? Try to make it for the annual wreathing of the lion statues that stand guard in front of the museum. It’s a popular tradition that signals the start of the holiday season. if you buy a Chicago CityPASS, it will include admission to the museum, which can be pricey for adults, but is free for kids under 14.
29 E. Ohio St.
You can’t leave town without tasting Chicago’s legendary deep dish pizza. Pizzeria Uno, just off Michigan Avenue, claims to have invented the deep dish pizza. It’s just under a one mile walk north from Millennium Park to Pizzeria Uno.
Day 3: Lincoln Park Zoo, Wrigley Field and World-Class Theater
Lincoln Park Zoo
2001 N. Clark St.
Chicago is one of the only cities to have a free zoo. That’s right, FREE! And it’s right in the middle of one of the most beautiful neighborhoods in the city, Lincoln Park. It’s a beautiful 1.5 mile walk from Michigan Avenue to the zoo, through some of Chicago’s toniest streets.
1060 W. Addison
After lunch, it’s a half hour walk (1.4 miles) to legendary Wrigley Field. Catch an afternoon game and stay for the 7th inning stretch singing of “Take Me Out to the Ballgame.” Have a Chicago style hot dog for lunch at the ball park.
Are your kids old enough to ride a bike on their own? If so, after the game hop on one of Chicago’s budget-friendly blue bikes. Chicago launched its bike rental program, called Divvy, in 2013. The Windy City’s bike sharing system costs $10 for a 24 hours pass. That gives you an unlimited number of trips, up to 30 minutes each. With some 5,000 bikes and 500 stations across the city, Divvy’s a fun, affordable way to get around. Ride a bike to the lakefront, then head south. Return your bike to one of the many downtown locations.
Top Off Your Trip with a Dose of Theater
Top off your three days in Chicago in style, with a trip to the theater. There are some 250 theaters in the Chicago region, from small storefront community theaters to established Tony award-winners like Steppenwolf. Leave one evening to enjoy it. Pick a dazzling downtown Broadway production or world-class Chicago Children’s Theater production. If you’re here over the holidays, don’t miss the dazzling holiday Nutcracker performance by the Joffrey Ballet or the Goodman Theatre’s annual “A Christmas Carol” production.
TraveingMom Tip: Only go to the Goodman’s Christmas Carol with older kids. It can get a very dark telling of the age old story.
Where to Stay During a 3 Day Visit to Chicago
You’ll want a centrally located hotel, with easy access to public transit, if you’re going to be able to cram all of this action into just three days. A few of our favorites: