To Do in Chicago With the Kids: Fun, Family Chicago Trip!

Visiting Chicago with the kids? Follow my guide of what to do in Chicago! Take it from a Chicago-mommy insider: Save this list of great, kid-friendly attractions and interests. These Chicago spots are fun for the whole family! You won’t want to miss these Chicago attractions and hidden gems with the kiddos!

As a nanny in the city for years, I would plan and organize many wonderful trips to these awesome, kid-friendly, Chicago attractions. I would attend a few of these locations on a regular basis with the kids I nannied. Many of these unique suggestions will please a family with kids of all ages, yet WON’T break the budget! Check out the guide of my top spots to visit in Chicago:

Visit Chicago’s Navy Pier Children’s Museum

I have spent full days at the Children’s Museum, on Navy Pier. If you attend regularly I would suggest buying the family pass. It is extremely reasonable, and you should opt for the parking pass as well. It will pay for itself after 2 visits! Then you can park inside Navy Pier’s underground parking, and as long as you head to the children’s museum for a bit, the parking will be covered! That’s a great insider tip! 😉 The exhibits are so interactive, memorable and the kids will have a blast. You could explore for days here and probably still not see everything!

Kohl Children’s museum Visit with the Family

If you’re willing to travel just a big outside of the city: to Glenview, IL., This hidden gem will not disappoint! Kohl children’s museum is under the radar, compared to Chicago Children’s Museum. Yet it offers a huge, entertaining and discovery space! Also, great parking and wonderfully interactive experiences for kids of all age! The last time I was there with my nanny family, the kiddos loved the mini Whole Foods shopping experience, as well as the water room, interactive music room, building & construction exhibit and the hands-on science experiments! If you have already visited the Chicago Children’s Museum, this would be such a wonderful option for your family adventure!

Explore Peggy Notebaert’s Nature Museum

Peggy Notebaert Nature Museum offers wonderful visits and ongoing camps all about animals, plants, science, exploration and the Earth. With interactive, hands-on learning for the kiddos at a super affordable rate (under $10 per person, regular admission). Kids under 2 and teachers are free!

Chicago attraction: Maggie Dailey Park

What an adventure! AND talk about that view of the city & the lake! The Maggie Dailey Park is truly fun for the whole family, with their insanely large outdoor play area. As an adult, I even had a blast running around with the kids!

Chicago Ferris Wheel on Navy Pier is an Unforgettable Experience

You can’t miss this Chicago experience! Ride the slow, brand new feeris wheel! The view is 360 spectacular! No need to worry, each car is completely glass enclosed for your family’s safety. Snap those pics while you are above the windy city! Treasure the unique, historical family experience of the Navy Pier Ferris wheel!

*BONUS Chicago Travel Tip: Navy Pier hosts a one-of-a-kind Fireworks display every Wednesday and Saturday night in Summer! It’s free to view the display, and so exciting! You can’t miss it!

Visit Tall ships at Chicago’s Navy Pier

Depending on what season you are visiting Chicago, the seasonal attraction of the ‘Tall Ships’ comes to Navy Pier every summer!

These amazing, beautiful ships dock right on Navy Pier for your enjoyment, many of the ships in the exhibit will also allow the public to come aboard and explore the ship, first-hand! Many actors also play the part of pirates and captains as you explore from ship to ship! It’s a great place to get photos of the family together, while learning the history of the beautiful tall ships!

Chicago Fire Engine Tour of the city

This is a very unique tourist attraction. Most people didn’t even realize this exists: You can actually ride on the top of a redesigned, retired fire engine AND you also visit the awesome fire station locations and many historical Chicago spots throughout the city!

My dad still works as a proud firefighter for The Chicago Fire Department. He planned a Fire Engine tour for our whole family this summer. It was an unforgettable experience! I have lived in Chicago my whole life yet this Fire Engine Chicago tour experience was such a unique treasure! I learned so many facts about our great city I did not know!

I loved seeing baby Harry’s Face as we took in the unique view of Chicago, while enjoying the historical facts and 360 degree view on the top of the engine! Our engine driver/ tour guide had a wonderful, knowledgable, entertaining personality as well! That made our experience such a blast!

Enjoy a Chicago Boat Tour of the city

Another great Chicago tour option truly unique to Chicago, is going on a Boat Tour! You can choose a River boat tour, or a Lakeview tour (from Navy Pier)! There are so many options to enjoy with the kids, or make it a romantic date night with dinner and dancing right on a boat of your choice!

Chicago’s Famous Museums

Not only is the view amazing from ‘Museum Campus’ but you will also explore 5 different HUGE, historical museums all in the same beautiful lake-front area! You can also check out each Museum’s special offers as well as kid’s days! The interactive, hand-on exhibits are so fun and creative. Dig into your kid’s passions and interests with Chicago’s Museums. Any one of our Chicago Museums will entertain and delight your child, creating lasting memories for all of you!

Millennium Park Chicago attractions

The open, grassy area and the ‘face’ fountains will give you some awesome Chicago memories! Cool off on our hot Summer days. Run through the huge, digital face-fountain and have a silly, excellent time with the whole family!

Ice Skating at Maggie Dailey Park

This is a truly unique Chicago venue to enjoy the winter sports with your family! Strap on some rented ice skates and enjoy the one-of-a-kind city view, as you ice skate together this winter!

Visit Zoo lights at Lincoln Park Zoo

If you are Chicago in the winter, Zoo Lights is a festive, bright and memorable experience! Most of the viewing takes place after dark, which is a unique zoo experience for most people! Sip your cocoa and peek at the festive monkey’s while you snap some family pics being silly together!

Enjoy one of our many Chicago Fests!

There is always a festival, food tasting or concert going on in Chicago! Our ‘Taste of Chicago’ as well as ‘Blues Fest’ are among the most popular. Every weekend there are multiple festivals (many with free entrance and live entertainment!) Some of my favorite local bands always perform in the summer Chicago outdoor fest and concerts! Bring the kids, dance in the streets, grab a ‘walking taco’, and jam to some Chicago Blues together!

Famous one-and-only Rainbow Cone on Chicago’s south side!

Many have tried to duplicate the taste and tradition… but none can compare to the original Chicago Rainbow Cone! Located on Western Ave., in my home town, Rainbow Cone is a treasured location with a famous name and even better taste!

Again, I love my sweets! I may be biased but in my opinion, you have to experience the best, unique combination of sherbet and ice cream flavors together. Get in the long line this summer and get your one-of-a-kind ice cream on Chi Town’s Southside! We make it a point to go to Rainbow Cone every year, this year was baby Harry’s first trip!

Chicago Family Trip



Chicago Park District: Splash Pads

Our Chicago Park District excels in offering programs and unique outdoor experiences for the whole family to enjoy! Just like the splash pads! The city of Chicago is building these every where now it seems! And we could not be more grateful.

When I was a nanny in the city, we had 4 different splash pads & playground within walking distance of the house! I was taking those adorable kiddos to a splash pad every day! We had a blast over the summer. Now, my own baby Harry enjoys the cool mist on a hot Chicago day! You can even spot me running through the water, too! We have a blast at the many parks across the city! Invite your tribe and cool off with some fun, friend time together at the park!



Visit Chicago Indoor Play Rooms

These indoor playrooms are all the rage in the city. Babies, toddlers and young children alike will enjoy exploring, jumping, sliding, crawling and playing in one of the many playrooms Chicago offers.

My favorites are:

Little Beans Playroom & Cafe 

Little Beans offers two locations to play: Chicago North side, and Evanston)

*Bonus- The Evanston Little Beans location has free parking, an entire gym space with a trapeze and jump zone, as well as a kids Karaoke room! A huge space with tons of exploring and fun!

Pickle’s Playroom in Lincoln Square: You can also get your kid’s hair cut there, in the cool play-time themed chairs! Afterwards, you can also walk over to the heart of Lincoln Square: see the fountain, and the outdoor band & entertainment (sometimes a clown guy makes balloon animals), and get your kiddos and yourself a very special treat: gelato at ‘Paciugo’. This mommy loves sweets! Paciugo’s home-made gelato offers such unique flavors: olive oil, lavendar and unique chocolate sorbet. The salted Carmel is to die for! Or you can hop over to ‘Cafe Sel Marie’ sit in the outdoor patio and view the fountain. Lincoln Square is absolute fun for the kids and the parents, as well!

See the Shedd Aquarium in Chicago

Not only does the Shedd offer a wonderful live water show (multiple times per day), but if you have toddlers, you cannot miss the penguin exhibit! (In the bottom level). Your little ones can jump, slide and explore, while dressed as a penguin in this unique, interactive children’s exhibit. They will learn about the lifestyle of penguins as they play in the adorable, little penguin play area.

The kids I would nanny used to love coming here. They would beg me during the week to take them to the penguins! We all had so much fun at the Shedd.

*Bonus- the entire penguin play space also faces the real-life penguins. Your kiddos can mimic their actions and sounds as they experience, imagine and play! Snap some adorable pics of your little penguin waddling around!


Visit one of Chicago’s many Beaches

The windy City is home to so many picturesque beaches! Explore the city and the Lake Shore. Surpassingly, it is as just as beautiful in the winter as the summer. Oak Street is super popular, but travel a bit more North to ‘Foster’ Beach to find a more relaxing atmosphere, still with a beautiful view. Foster beach is less busy, and parking is super easy. Bring your beach chairs and check out the skyline. Our Chicago beaches offer you the relaxation, the views, and the buzz of our sweet home, Chicago!


This guide will help you plan your next Chicago Family trip. No need to worry about what to do with the kids. If you have young kids, I have your Chicago tips and hot spots to visit!


What other unique attractions have you discovered in Chicago for the kids? What else can I add to this awesome list? Please message me and let me know! I love to keep this guide updated and useful for my fellow mamas!


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Hi, I am Kelly! Creator and administrator of Little Hat Family, I absolutely adore my squishy, smiley, 10-month old son, Harrison (Harry), and my kind and cooperative husband Stefan. Our little millennial, hipster family lives in Chicago and yes, we do love hats!
As a professional nanny for 11 years in Chicago, and now a new mommy myself, I have picked up so much useful, modern, mommy advice and life hacks! I would love to pay it forward to my fellow mommy tribe!
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