Tips for Traveling to Chicago with Kids

After catching the “Big City Bug” traveling to NYC last year for spring break, our kids were begging to visit another big city. Being city lovers ourselves, we happily agreed and decided to travel to The Windy City! I hadn’t been to Chicago in nearly 30 years myself, so I was overly excited and jumped head first into planning our trip. We wanted a nice mix of touristy venues and time for self-exploration. We love to just stumble across things and enjoy the ride! Chicago did not disappoint.

When to Go

When I mentioned Chicago by its nickname, The Windy City, it certainly lived up to its name! We were there in March and it was brisk and chilly, exactly what we were looking for. The weather in March is ever changing and it can be snowing (we had some flurries, much to the kids’ delight!) or it could be cool and rainy. The one thing that is constant is the wind. We had days with light winds and one day where the gusts were so big that it almost knocked over my petite 45-lb. 6-year-old! It really depends on what you are looking for when you travel, but late spring, early summer, and early fall are the favorite times for most to visit Chicago. There are more outdoor attractions open that were not open when we were there. The temperature is much milder and outdoor festivals are the norm.

Where to Stay

We stayed in the River North area of Chicago. The walkability was perfect and everything we needed was right there. Being right on the Chicago River was really cool for the kids because we were there for St. Patrick’s Day weekend and watched them dye the river green! Tons of cool, delicious restaurants were within a five-minute walk. The Magnificent Mile (Michigan Avenue) is also another good area to stay in. It took us about five minutes to walk there from our hotel. Tons of amazing shopping on The Magnificent Mile!

What to Do

The possibilities here are endless! There are so many attractions to see. The CityPASS Chicago is a great option and makes visiting most of the iconic attractions much more affordable. The CityPASS also gives you more perks than just buying a general admission ticket, for example you get expedited entry to most attractions, all-access passes where you don’t have to pay for extras, etc. The CityPASS Chicago offers admission to The Shedd Aquarium (priority entry), The Sky Deck Chicago (day and night admission), The Field Museum (all-access passes), The Adler Planetarium or Art Institute of Chicago, and the Museum of Science and Industry or 360 Chicago Observation Deck-express entry.


The Shedd Aquarium: We have been to our fair share of aquariums, being native Floridians. Hands down, The Shedd Aquarium had the BEST animal show we’ve ever seen. We were fortunate enough to get front-row seats and got to experience a seal walk out and do a little demonstration three feet away from us! Another thing we loved about The Shedd Aquarium were the exhibits from all over the world. There were tanks with fish and plants from the Amazon, the deep ocean (so rare to see!), the Caribbean reef, the Great Lakes, and various rivers from around the world. The Beluga Whales were majestic to watch and the dolphins were so playful. The lower level is all underwater observation and it was really cool to watch them play and interact underwater!

Skydeck Chicago: This one had me biting my nails in anticipation for days! I am the scaredy cat of the family when it comes to heights. The Skydeck Chicago is located in The Wilis Tower (formerly known as the Sears Tower). It was the world’s tallest building until 1998, standing at 1730 feet tall and 110 stories, including the antenna. This building was built to sway six inches from its true center on windy days. On a clear day, visibility is 50 miles! You can see Illinois, Indiana, Wisconsin, and Michigan. The views are crazy impressive. The best part of the Skydeck is The Ledge Experience. This is what had me biting my nails! You actually walk out onto a glass-paneled box, hanging off of the building, with vertical views to the ground 103 stories below. This was a highlight for my kids. While I was absolutely terrified and walked onto the ledge with my eyes closed for the picture, they spent our time laying on their stomachs looking at the ground below! Such a fun experience. The CityPASS actually allows you to visit once during the day and once at night on the same day. I would recommend calling before heading out and double checking the visibility. We went from zero visibility to full visibility in the course of an hour.


The Field Museum: The Field Museum was my favorite stop of the trip! With our CityPASS we were able to go into the special limited-time exhibit featuring mummies from ancient Peru and Egypt. It was absolutely incredible. You can actually see inside the mummies by the use of non-invasive CT scanning. The exhibit is tastefully and respectfully done and we learned so much. Each area of the exhibit has an interactive area for kids (and let’s be honest, adults). There are interactive touch tables that you can touch that move an image of the mummy around in 3D so you can see what’s inside. The other favorite part of this museum was the Griffin Halls of Evolving Planet and SUE the T. Rex in the Elizabeth Morse Genius Hall of Dinosaurs. What makes SUE so special? Well, first of all “she” (they are unsure if SUE is a she or he — SUE is named after the person who found her in South Dakota, Susan Hendrickson) is from 67 million years ago! WHAT?! SUE is also the largest T. Rex ever found and the most complete at 90 percent. SUE’s head is in a separate display because of its delicate condition and the fact that it weighs over 600 lbs. There is an exact replica cast on the display and her head is displayed nearby. There is an area outside of the exhibition that has scientists working on and uncovering actual fossils with viewing windows, so you can see them at work with their tiny, delicate tools. It was exciting to watch them work. There are signs displayed in the window for the museum guests to see what fossils the scientists are working to uncover and how old they are expected to be.

The Adler Planetarium: The Adler Planetarium is located on Lake Michigan near the Field Museum and Shedd Aquarium. This wasn’t our favorite stop, but we definitely enjoyed our time there. They have an extensive collection of antique instruments and our favorite exhibit there was an original planetarium that you get to ride inside.


Navy Pier: We visited the Navy Pier on the windiest day we were in Chicago. This is where the wind almost took my child down! Located right on Lake Michigan, it was extra windy. We loved walking through the indoor area with shops and restaurants and then through a tropical greenhouse on our way outside, where you are greeted with an enormous Ferris wheel. My fam took a ride while I sat that one out. They loved it but the wind gusts scared the kids while they were stopped at the top. I’d definitely say it’s not for the faint of heart. During the milder weather months, there are other attractions such as a flying swings ride and a climbing wall. The thing here that most impressed the kids was the giant floating chunks of ice in Lake Michigan — Florida kids!

The Bean: Actually called the Cloud Gate, the Bean is on your way to most of the other venues and definitely worth the stop for the perfect family selfie!

Maggie Daley Park: Maggie Daley Park was easily the best park we have ever been to. This 20-acre park is located near Lake Michigan. It boasts a one-quarter mile ice skating ribbon, rock climbing walls, and our favorite, a three-acre playground called The Play Garden. I’ll let the pictures speak for itself, but it has the most incredible tower slides, suspension bridges, talking tubes, rope climbs, hills — I could go on and on. We could’ve spent an afternoon here. This is best for ages 5-12.

Did we visit all of your favorite family-friendly places? Tell me more, because the Kwartler Family will definitely be back!

Johanna Kwartler
Born and raised in St. Augustine, Johanna moved to Jacksonville to attend UNF and never left! Now this former elementary school teacher turned Stay at Home Mom to Hudson and Callie, and wife of 13 years to Matt, enjoys life at the beach. Johanna enjoys being room mom and volunteering at the kid’s school as PTA President. She also in an avid runner, and loves working out at The Gym Jax!


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