Things to Do in Chicago with Kids

Chicago collage 2Traveling to Chicago or planning to be a tourist in your own city? With so many vibrant neighborhoods, acclaimed restaurants, towering skyscrapers and hip-shaking entertainment, it can be a trick to put together an itinerary that works best for your time, budget and kids. We’ve narrowed it down to the best of all the greats in the second city (and some of them are even free!).








  • Cloud Gate (also known as The Bean) at Millennium Park 1 of 21
    Cloud Gate (also known as The Bean) at Millennium Park
    Ask a Chicagoan on the street to point you to the Cloud Gate and expect to get a quizzical stare in response. But bring up "The Bean" and most city-dwellers will smile and tell you exactly where this beloved outdoor structure sits in Millennium Park. The 110-ton seamless stainless steel installation was created by British artist Anish Kapoor and inspired by liquid mercury. Snap plenty of photos of what's reflected in The Bean -- the skyscrapers, the sunshine, the inevitable marriage proposal, and yourself! Click here for more information.
  • Jay Pritzker Pavilion at Millennium Park 2 of 21
    Jay Pritzker Pavilion at Millennium Park
    This state-of-the-art pavilion that features curved steel, astounding acoustics and a 95,000 square foot lawn area with 12,000 seats is where you can put down your picnic basket to enjoy music, dance lessons and free entertainment all summer long. If you are downtown for the day, spend sunset here, taking in the music and scenery in the heart of the city. Click here for more information.
  • Buckingham Fountain 3 of 21
    Buckingham Fountain
    One of Chicago's most magnificent landmarks is the Clarence F. Buckingham Memorial Fountain, built in 1927 and dedicated by donor Kate Buckingham to the people of the city. Everything about the fountain is magnificent, from the hourly light show originally designed by Buckingham to mimic "soft moonlight" to the more than 14,000 gallons of water per minute that circulate through jets and displays. Open from April to mid-October, depending on the weather, with light shows on the hour for 20 minutes. Click here for more information.
  • Second City Theatre 4 of 21
    Second City Theatre
    The sketch comedy and improv stages at Second City have lit up the careers of greats Tina Fey, Amy Poehler, Stephen Colbert, Steve Carrell, Mike Meyers, John Candy, Gilda Radner, Bill Murray, John Belushi and 500 more recognized names in the business. Established more than a half-century ago, The Second City entertains a million audience members a year with its theaters in Chicago and Toronto and touring ensembles. Shows are scheduled every night of the week and could feature SNL's next breakout star. Click here for more information.
  • ”¨Garfield Park Conservatory 5 of 21
Garfield Park Conservatory
    With six lush greenhouses, children's gardens, workshops and two expansive exhibition halls, the Garfield Park Conservatory is a pocket of peace in the center of a bustling city. Choose one of several tours to take in the plants, flowers and art -- all of it for free as a part of the Chicago Park District programming. Click here for more information.
  • Willis Tower SkyDeck & The Ledge 6 of 21
    Willis Tower SkyDeck & The Ledge
    While you're peering down at the city from the Skydeck level of Willis Tower (rebellious Chicagoans adamantly still refer to it as the Sears Tower), be sure to step out on to The Ledge. These four glass balconies that are clear on all sides jut out from the Skydeck to offer breathtaking views you won't replicate anywhere else in the city -- totally worth shaking off your jitters to experience! Click here for more information.
  • Magnificent Mile 7 of 21
    Magnificent Mile
    This 13-block stretch of downtown runs from the banks of the Chicago River to Oak Street and is packed full of stores, restaurants, hotels and theaters. Trees that line the Mag Mile are lit year round as a backdrop for events like the Holiday Lights Parade in the winter and horse-drawn carriage rides in the summer months. Enjoy street musicians as you wander from the Apple store to American Girl and down to the original water tower that survived the Great Chicago Fire. Take a trolley tour of the sites, enjoy tea at the historic Drake Hotel and take the elevator up to the top of the John Hancock for city-wide views and a special dinner at the famed Signature Room at the 95th restaurant. Click here for more information on the Magnificent Mile and click here for more information on the John Hancock Center.
  • Chicago Theatre 8 of 21
    Chicago Theatre
    The majestic downtown theater has presented live entertainment for nearly a century, including greats like Jack Benny, Duke Ellington, Diana Ross, Dave Letterman and Alicia Keys. Tour the theater for just a few dollars or snag tickets to an upcoming show inside the grand auditorium. And if nothing else, be sure to take a photo in front of the iconic Chicago sign on that great street, State Street. Click here for more information.
  • Wrigley Field & US Cellular Field 9 of 21
    Wrigley Field & US Cellular Field
    Half of Chicago's residents will insist that you sit in the bleachers to cheer on the Cubs while you're in the city, and the other half will demand that you side with the White Sox at US Cellular Field. All of us will agree, however, that you must go out to the ballgame if you're in town for the baseball season.

    Wrigley Field, nearly a hundred years old and known as The Friendly Confines, sits on the north side of the city, surrounded by plenty of restaurants, bars and public transportation.

    Go south to find US Cellular Field, with plentiful parking in the lot and fantastic fireworks before every game, after every White Sox home run, and after all home-team wins. Search deal sites for affordable packages that include seating prices, buffet dinner and drinks and batting practice admission.

    Click here for more on the Cubs at Wrigley Field. And also click here for more on the White Sox at US Cellular.
  • Deep Dish Pizza 10 of 21
    Deep Dish Pizza
    You're in Chicago, why not sample its premier dish? Join the rest of us in debating which place rolls the most buttery dough, whether it should be topped with cheese or sauce, and if you can stay vegetarian after one slice of the sausage. No matter where you weigh in, know that you will not want to go back to thin ‘n crispy after digging into deep dish. Click here for more on reviewer recommendations for best pizza spots. And then click here for Zagat reviews on the city's best 'za.Finally, click here to have Chicago pizza delivered to your hometown.
  • Chicago-Style Hot Dog 11 of 21
    Chicago-Style Hot Dog
    Skip the ketchup and shake on the celery salt if you want to devour a Chicago-style hot dog. From the ballpark to a hole-in-the-wall sandwich stand, you can keep yourself busy in the city simply by doing a taste test of all the dogs we offer. Although it doesn't make the list for best hot dogs, SuperDawg drive-in serves up more kitsch and history than anyone else steaming hot dogs in the city limits. Click here for a food reviewer's top dog picks.
  • Field Museum 12 of 21
    Field Museum
    Built as a part of the World's Columbian Exposition in 1893, this museum was renamed in honor of benefactor and legendary Chicagoan Marshall Field nearly ten years later. As a home to natural history artifacts, collections and research, the Field Museum is most famous for hosting SUE, the world's largest and most complete T.rex ever discovered. At 67 million years old, SUE still captures the attention of crowds of visitors each day. Be sure to tour the Egyptian mummies, the traveling exhibits and watch as scientists examine fossils in glass-enclosed labs. Click here for more information.
  • Chicago Architecture Foundation 13 of 21
    Chicago Architecture Foundation
    The Chicago Architecture Foundation is a treasure for visitors and residents alike, offering tours, exhibits and historical information through well-trained guides who will wow you with their knowledge of the city. Boat tours are a great way to spend a few hours listening to stories about the City of Big Shoulders, while walking tours and L-train tours will get you into the heart of Chicago's diverse neighborhoods. Many exhibits on-site are free to the public. Click here for more information.
  • National Museum of Mexican Art 14 of 21
    National Museum of Mexican Art
    This free museum that houses more than 7,000 objects and artifacts in its permanent collection was founded by Chicago Public School teachers with a budget of only $900. Today, more than 60,000 school children and thousands more supporters visit each year to take in the art and culture from both sides of the border on exhibit. Click here for more information.
  • Holiday Train 15 of 21
    Holiday Train
    If you're in town to do holiday shopping, take in the sites and the lights on the Chicago Transit Authority's holiday el train. Decked inside and out with thousands of lights, trees and decorations, the train also pulls Santa and his elves through the city to spread holiday cheer to public transportation travelers. Find the holiday train schedule here. Click here for more information.
  • Peggy Notabaert Nature Museum 16 of 21
    Peggy Notabaert Nature Museum
    Take a break from traffic and noise by stepping into the calm and curious environs inside the Peggy Notabaert Nature Museum in Lincoln Park. Filled with science exhibits and hands-on kids programs, it is the perfect stop for families. Be sure to spend time in the heart of the museum, the Judy Istock Butterfly Haven, a greenhouse filled with 1,000 exotic butterflies of more than 75 species -- some of which will fly past in flirtation or land gently on your shoulder while you wander past the pools and greenery where they live. Click here for more information.
  • Steppenwolf Theatre 17 of 21
    Steppenwolf Theatre
    With three stages, a roster of 16 plays and nearly 700 performances, readings and events every year, Steppenwolf Theatre has exploded, season after season, since it was founded by Jeff Perry, Gary Sinise and Terry Kinney in a suburban church basement. The ensemble is made up of 43 actors, many of whom you will recognize and some who you may even spy in the audience. Steppenwolf sets always wow and the productions will surely get you thinking. Main-stage shows often include a discussion with cast or crew that is worth sticking around for. Click here for more information.
  • Navy Pier 18 of 21
    Navy Pier
    Navy Pier is the #1 tourist destination in the entire Midwest, hosting 8.6 million visitors a year, who ride the oversized ferris wheel, visit the Chicago Children's Museum, tour the Tall Ships and take in circus shows or catch a dinner cruise. Navy Pier is never more fantastic than during free fireworks shows that light up the shoreline and echo off of the surrounding skyscrapers. Click here for more information.
  • Art Institute 19 of 21
    Art Institute
    The two large lion statues that don oversized wreaths and red bows in the winter, watch over 1.5 million visitors from around the globe who walk through the doors of the Art Institute each year. A permanent collection of more than 300,000 works of art, dozens of special exhibits and a packed-full schedule of lectures and events are inside the eight buildings in downtown Chicago. There is plenty to engage art lovers of all ages, family tours, several dining options and free apps to walk you through the collections. Click here for more information.
  • The Picasso 20 of 21
    The Picasso
    Once controversial, this 50-foot, 160-ton lady is now iconic in the city. The sculpture was commissioned in 1963 for Daley Plaza, and took artist Pablo Picasso two years to create. He offered it as a gift to the people of the city, and in his dedication letter declined to explain what the artwork represents. Join city workers and attorneys for lunch on the plaza, listen to musicians who play for change on the corners and pose next to the public art for what is likely your only opportunity to actually touch a Picasso! Click here for more information.
  • Lake Shore Drive 21 of 21
    Lake Shore Drive
    Originally built built by the city at the urging of wealthy Chicagoan Potter Palmer, who wanted to enhance the value of his mansion on Lake Michigan with a place where the affluent could leisurely drive in their carriages, this thoroughfare is now designated as a part of US Highway 41 that runs from the north end of the city to the south. Follow the s-curves of LSD (also known as The Drive or the Outer Drive) and you will recognize locales from classic movies like "Risky Business" and "When Harry Met Sally" and "Blues Brothers." Even better, you can easily exit for access to Lincoln Park Zoo, Millennium Park and the museum campus, all while getting breathtaking views of historic architecture, the skyline, beaches and the lake. Click here for more information.

Read more of Jessica’s adventures as a single mom in the city at Sassafrass. Meet up on Twitter.  Ogle shoes together on Pinterest.

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Article Posted 4 years Ago

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