Chicago is easily one of America’s most family-friendly and culturally diverse cities. It’s home to The Willis Tower (formerly known as the Sears Tower), which is the second tallest building in the U.S. It’s also home to delicious deep-dish pizza and a plethora of interesting culture, attractions and family fun.
Families making their first trip to the Windy City may be a bit overwhelmed by how much there is to see and do, but don’t worry; we’re here to help! Welcome to a Chicago weekend getaway with kids.
Written by Maxwell Barna
Day One: Photograph the Icons
Begin your 48 hours in Chicago with a visit to Millennium Park. Especially fun in the summer, the park features Crown Fountain, with two 50-foot, LED-laden columns and a cascading waterfall. It's the perfect way to cool off on a hot day! There's also Lurie Garden, perfect for a walk and picnic. And, of course, you have to see the park's most famous sculpture, "The Bean." This 110-ton behemoth structure, formed from 168 stainless steel plates, is like a giant fun-house mirror. Kids love running around and under the structure, watching their reflections change. In the summer months, the park offers family-friendly programs and concerts.
Cross the street to continue to Grant Park and visit the iconic Buckingham Fountain. The famous fountain shoots water 150 feet into the air in a spectacular 20-minute water show every hour, on the hour.
Now that you are in the parks, you're steps away from the Museum Campus, which comprises three family-friendly institutions: Adler Planetarium, Shedd Aquarium and Field Museum of Natural History. It's too ambitious to try to see them all on a Chicago weekend getaway with kids, so pick one and spend the afternoon exploring. Which will it be? Dinosaurs, sharks or stars?
You can't go to Chicago without a stop at the Navy Pier, and as the sun sets and the carnival lights turn on, kids will love a ride on the Ferris wheel, the Light Tower Ride, or the musical carousel. The pier is also home to the Chicago Children's Museum, as well as shops like Build-A-Bear and restaurants like Jimmy Buffet's Margaritaville -- you'll be able to spend hours here!
Day Two: Tour the Ins and Outs
Whether you're a Chicago Cubs fan or not, you should consider a tour of Wrigley Field, America's second-oldest Major League Baseball stadium. You'll see the mound where Babe Ruth made his "Called Shot" in the 1932 World Series! Visitors also learn about the interesting connection between Wrigley's chewing gum, and get to see the indoor batting cages, the team's dugout and clubhouse and the press box.
Spend the afternoon at Skydeck Chicago, located inside the Willis Tower. Visitors take a 60-second elevator ride to the 103rd floor, where they stand 1,353 feet above the ground! On a clear day, visitors can see straight across Lake Michigan into Indiana, Wisconsin and Michigan. Visitors are also encouraged to step into one of the Skydeck's retractable glass balconies, which extend four feet out from the building. You'll look straight down and see nothing but the street, over a quarter-mile below.
Afterward, take a boat tour up and down Lake Michigan with Wendella Boat Tours. Architectural city tours leave by the Trump Tower and Wrigley Building and range from 75- to 90-minutes. The guided tours give you a chance to kick back and take in the sites along the Chicago River and the shore of Lake Michigan.
Spend the evening at Tommy Gun's Garage Dinner and a Show. At the only speakeasy in town, the whole family is transported back to prohibition-era Chicago. You'll see period-correct memorabilia, silent movies and old cars. Rates include dinner, followed by a comedy-action show that includes dancing, singing and audience participation. Plus, kids 11 and under receive a free souvenir! Open Wednesday through Sunday.
Day Three: Visit the Animals
If you need a break from downtown Chicago, head to Brookfield Zoo, about 20 minutes away. If you plan to visit, however, dedicate a whole day here; it's a vast area, and can get very crowded.
Where To Stay: Luxury Chicago Hotel
Where to Stay: Mid-Range Chicago Hotel
Where to Stay: Budget Chicago Hotel
Top 5 Chicago Restaurants Not To Miss
In The Windy City, hot dogs are king, especially at Wrigleyville Dogs, just a block away from Wrigley Field. Get a classic hot dog, Chicago-style -- but remember it is considered "bad manners and harmful to your taste buds" to put ketchup on a Chicago hot dog!
2. Gino's East of Chicago
Chicago is known for its deep-dish pizza, and Gino's is the home of the legendary Chicago pie. The downtown original is located on East Superior Street, and kids will love having a chance to literally leave their mark by writing on the walls! (Bring a Sharpie, although most of the servers will have one.) Every inch of the restaurant is covered in graffiti, including chairs and tables, and you'll have the best deep dish in town.
3. Billy Goat Tavern
Cheezborger, cheezborger! Remember the SNL skit with John Belushi, Dan Aykroyd, Bill Murray and Loraine Newman? This is where it took place! Kid-friendly fare includes hot dogs and grilled cheese sandwiches.
4. Ed Debevic's Short Order Deluxe
At this 50's-style diner, it's less about food and all about attitude! Families love the waiters, who are known for their playfully salty, stubborn attitudes -- they'll poke fun at you! They also get up onto the countertops and dance every half-hour.
5. Margie's Candies
Another foodie landmark, Margie's Candies has been a city staple for over 90 years. Kids love the homemade chocolate and candies, as well as more than 10 flavors of 100 percent homemade ice cream and toppings. There are two locations -- one at 1960 N. Western and one at 1813 Montrose.
Planning & Tips
If weather plays a factor in your family's decision making, we recommend a Chicago weekend getaway with kids in the fall. Winter is bitter -- they don't call it The Windy City for nothing! If you still want to visit with kids during the winter, however, go for St. Patrick's Day, when the Chicago River is dyed green! Spring is warmer, but wet, and summer can be quite balmy.
Summer and fall offer plenty of tours, festivals and concerts, including the Chicago Blues Festival, Lollapalooza, the Chicago International Film Festival, the Chicago Jazz Festival, a slew of fall foliage tours and more.
Regardless of when your family comes to Chicago, we recommend the Chicago CityPASS. Passes provide admission to five of the city's most popular must-see attractions, including the Shedd Aquarium, Skydeck Chicago, The Field Museum, Museum of Science and Industry, John Hancock Observatory, Adler Planetarium and the Art Institute of Chicago.
Chicago has the nation's second largest public transportation system. You can load any amount of money on to a city transit card, use cash, or buy one-, three- and seven-day visitors passes, which allow unlimited amounts of rides between specific time periods. Children under 7 ride free to ride, and children 7 to 11 can ride for a reduced fare.
Driving a car isn't the ideal way to get around Chicago, but it's not impossible. The biggest issue, however, is parking. There aren't many options, and the parking that is available is generally expensive. There are plenty of parking garages, but their rates tend to vary. Your best bet will be to leave the car at your hotel. If you're heading to the Brookfield Zoo and don't want to pay an exorbitant parking fee, check out the residential areas right outside the zoo's south entrance.
The Chicago Transit Authority is responsible for the city's trains and buses. The city has an underground and above-ground train network, known as the L, which travels to most of the city's popular tourist sites. Single rides are $2.25.
Single rides are $2 with a Transit Card or $2.25 with cash.
While more expensive to travel, you certainly can't beat the convenience of a cab. Uber and Lyft are also an option.
Our team of parents and travel experts chooses each product and service we recommend. Anything you purchase through links on our site may earn us a commission.