Chicago is a city that doesn’t disappoint. Museums, sporting events, parks, theater and nightlife all make Chicago appealing. It’s the third largest city in the United States, yet it’s easy to navigate and most sights and attractions can be covered in three to four full days. With a seven and almost five-year-old in tow, our family set out to see, hear, touch and taste what the city has to offer. Here are a few of our favorite experiences for what to do in the Windy City with kids.
Millennium Park
Millennium Park is the Loop District’s gathering place. Ideal for people watching, picnicking or interacting with the art structures. Cloud Gate or “The Bean” as it’s known to locals, offers unique reflections of visitors and the city’s skyline. The Crown Fountain thrills as waders anticipate when the fountain’s faces will spew next. The interactive art was fun for the kids. They liked making goofy faces in The Bean and kicking water in the Crown Fountain. Bonus: it’s FREE
Navy Pier
Chicago has a special connection to Ferris wheels. It’s that connection and the Pier’s adventure park that brought us to Navy Pier. The Pier’s Centennial Wheel pays homage to the city’s special place in Ferris wheel history. The very first Ferris wheel was unveiled in the city at the 1893 World’s Fair. It’s fully enclosed cars allow riders tummy tickling views of the city and Lake Michigan. The Pier also has a few restaurants and fast food options, so we let the boys choose where we ate. Allowing them to choose, even if it was McDonald’s, kept them happy and gave us leverage for when it came time to choose a restaurant for dinner.
Ohio Street Beach
Just a few blocks from Navy Pier is Ohio Street beach which is another fun thing to do with kids in the Windy City. Smashed against the bustling city, it offers an escape from the chaos. Beach amenities include lifeguards, lockers and a cafe. With the iconic Hancock Building as a backdrop, we hiked up our shorts and leaped in at Ohio Street beach. Our beach stop allowed the boys to play in the water while we plopped ourselves in the sand with a beverage.
River Cruise
Chicago is known for its architecture so we carved out time in the itinerary for a boat tour. Cruises from various providers leave so frequently that we didn’t need advanced tickets. I enjoy guided tours as you typically hear personal stories from a local guide as well as learn a bit of history. The bonus of a boat tour is that your feet get a rest and there’s beverages and snacks available on board. For the boys, the narration was not as entertaining. They did however enjoy being on the water, passing under bridges and trying to locate the unique features of various buildings.
SkyDeck at Willis Tower
Skydeck and the Ledge at Willis Tower provide edge of your seat vistas of the lake, the city and on a clear day good chunks four states; Illinois, Indiana, Wisconsin and Michigan. Though lines for the tower can be long (go early and purchase advance tickets online) we entertained ourselves with the interactive displays while waiting. Once on the 103rd floor, we inched our way onto the Ledge. We were all a bit uneasy walking out onto less than 2 inches of glass suspended 1,353 feet above Wacker Drive. On shaky knees and with nervous laughter, we crept out and were able to snap these pictures. Memory made.
Eat Pizza
You can’t come to Chicago and not eat pizza. The city has enough pizzerias serving up saucy Chicago style deep dish that you might be able to eat at a different one every night. Pizzeria Uno, Gino’s East, Giordano’s and Lou Malnati’s are among the most popular, with lines outside their restaurants and hour long waits (just for seating). We chose Gino’s because it was close to our hotel. I appreciated that they had us place our pizza order while we were waiting to be seated (since cooking a deep dish pizza also takes about an hour). Turns out, you can come to Chicago and not eat pizza. We discovered our boys are not fans of Chicago style za. Chicken strips for the win.
Stroll Michigan Avenue
Water Tower Place 
Dylan’s Candy Bar 
K9s for Cops 
Garrett’s Popcorn
Known for its high-end shopping and dining experiences, the Magnificent Mile along Michigan Avenue is a destination for any trip to the Windy City with kids. Even though our boys are not shop till you drop fellas, they did enjoy the ambience and the sights on the Mile, plus we bribed them with popcorn and a stop at the candy store. On our boat tour we’d heard about Mrs. O’Leary’s cow and the Great Chicago Fire of 1871 so Paxton was excited to see the Chicago Water Tower. The water tower was one of just a few structures to survive the devastating fire. Bridger had to hug practically all 100 fiberglass dog statues along the Mile. The statues are part of the K9s for Cops Police Memorial fundraiser. They adorn the Mile each summer between Memorial and Labor Day.
Field Museum
Little boys and dinosaurs go hand and hand so a stop at the Field Museum was a must. There are many great museums in Chicago; the Museum of Science and Industry, the Field Museum , the Art Institute of Chicago, the Adler Planetarium, and the Shedd Aquarium to name a few. We chose the Field because when we visited in 2017 the museum was hosting Jurassic World: the Exhibition. The Field has excellent displays on ancient Egypt, dioramas on wildlife and several dinosaur fossils. The Jurassic Exhibition was the boys’ favorite with 24 foot tall animatronic dinosaurs that brought the Jurassic period to life. It was so well done that Bridger actually believed we went to Isla Nublar and saw real dinosaurs. Our stop at the Field Museum as a trip favorite on our trip to the Windy City with kids.
Take Me Out to the Ballgame
Growing up in North Dakota and having no major league sports teams in his home state, Scott became a fan of the Chicago Cubs. He and several friends make an annual pilgrimage to Wrigley each year. When we decided to take our family to Chicago, a game at Wrigley went without saying. Even if you don’t cheer for the Cubs or you’re not a baseball fan, one can appreciate the history and spectacle of a 105- year-old ballpark. The area around Wrigley has recently undergone a revitalization, so there are new restaurants and bars in the area each year. We came to the field early to be sure to beat the dinner crowds and enjoy the atmosphere; a Cubs win was an added bonus.
Twilight Bus Tour
Nightlife on a family vacation does not include rooftop drinks, so we opted to board a double-decker bus for a rolling tour of the city. The tour covered many of the sights we had seen over the passed day and a half days, but this time in their evening glow. We allowed Paxton to take his iPad on the tour and all the pictures above were taken by him. The boys were more entertained by the bus tour. Maybe the fact that they got to ride atop an open air double-decker bus had something to do with it, or maybe it was the story of the guy who tried to scale the Hancock Tower dressed as Spider-man. Either way, the twilight tour was a fun way to end our time in the Windy City and was one more fun thing to do in the Windy City with kids.
Bonus
Lin Manuel Miranda’s Hamilton is touring the United States and has long standing productions in Chicago, London, New York, San Francisco and Australia. We didn’t go to see the performance while on our 2017 family vacation, but did take advantage of a work trip to see the show. When planning a trip, we typically browse through ticket selling websites to see if there are any concerts, performances or professional sporting events we want to see while we’re in town. We’ve been able to see artists and shows that maybe don’t make it to our part of the country. Seeing Hamilton was certainly a site in Chicago that left a lasting impression.
More recently, we returned to Chicago with our boys to partake in all the holiday fun Chicago offers. Read more about our Chicago at Christmas time trip here.
Happy Adventuring, Rochelle