Chicago Family Vacation: 30+ Chicago Bucket List Ideas!

Planning a Chicago family vacation or staycation? This Chicago bucket list has 30+ ideas for family fun in the Windy City! From museums, parks, and beaches to food, tours, and adventure, these are the Chicago family activities you don’t want to miss. 

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Is Chicago a Good Place for a Family Vacation?

Chicago is a large city with a ton  of diversity. There are plenty of indoor and outdoor activities for all ages and interests, and an amazing, walkable downtown area. A family trip to Chicago is definitely a fantastic idea!

We spent fourteen years in Chicago exploring everything the city has to offer. Chicago is well known for delicious deep dish pizza, Wrigley Field, and stunning architecture, but there’s so much more. 

Wondering how many days are enough to visit Chicago? We would recommend at least a weekend to see the main attractions in Chicago and eat some good meals. However, it would be very easy to spend a week in the city and never tire of the food, culture, and endless attractions.

These are some of our favorite family activities in Chicago – get ready to check off your Chicago bucket list!

Chicago Museums for kids

You can spend the entire day visiting Chicago museums! There is something for all ages in Chicago. While we do acknowledge that museums are educational, the kids don’t have to know.

Shedd Aquarium

Opened in May of 1930, Shedd Aquarium quickly became a Chicago landmark. Shedd Aquarium is a sanctuary that supports global conservation programs, and they were the first aquarium to have an educational department.

The aquarium can get quite busy; visiting early on Sunday mornings is your best bet if you want to avoid the crowds.

Adler Planetarium

The Adler Planetarium is a great place to explore with kids. There are plenty of hands-on exhibits detailing space exploration and astronomy, as well as numerous sky shows!

The Field Museum

The Field Museum is known for its dinosaur exhibits, hall of gems, and artifacts from around the world.

It’s located on “Museum Campus” next to the Shedd Aquarium and walking distance to the Adler Planetarium. Consider purchasing a Chicago CityPASS to get discounts on admission for all three of these fun places for kids in Chicago! 

Museum of Science and Industry (MSI)

Quite possibly our favorite museum in Chicago, the Museum of Science and Industry does not disappoint. There’s a full size U 505 submarine, airplanes, and a train.

Kids will love the chick hatchery, the science of storms, and the coal mine, but that’s just the beginning. Plan on spending half a day or more in this awesome hands-on museum.

Art Institute of Chicago

Most families try to avoid art museums, but we’ve always found a way to entertain kids at a museum. Some of the highlights include their impressionist collection (Renoir, Monet, Van Gogh, and Degas to name a few), the Thorne Miniature Room, American Art, and medieval art.

Try one of the museum’s treasure hunts and the kids will never complain.

Chicago Children’s Museum

When it comes to kid-friendly things to do in Chicago, don’t miss this three story museum with everything from a dinosaur dig and multiple play structures, to a tinkering lab and water play station. Located inside Navy Pier, there’s plenty to do for kids age 10 and under.

Chicago History Museum

What kid doesn’t want to dress up like a hot dog? That’s one of the many interactive exhibits kids will love in this museum that covers Chicago history through the years.

Peggy Notebaert Nature Museum

Exhibits at the museum include everything from live animals to kid friendly play spaces to nature trails. This museum is a hands-on education for all ages.

Chicago Zoos

Do you have an animal lover in your family? Definitely add these zoos to your Chicago summer bucket list!

Lincoln Park Zoo

Lincoln Park Zoo is located just a few minutes north of Chicago and is a picturesque oasis for animals of all kinds. It’s one of the few FREE zoos left in the country. Admission to some zoos is $30+ per person, but this Chicago zoo is FREE!

Brookfield Zoo

The Brookfield Zoo is massive, spanning over 216 acres so plan to spend the day exploring. Favorite exhibits include the penguin encounter, Great Bear Wilderness (with polar bears), and the Hamill Family Zoo (complete with animal encounters). Kids love it!

Chicago Gardens

These beautiful gardens are among the best things to do with kids in Chicago. And totally Instagrammable if you have teens on your Chicago family vacation!

Chicago Botanic Garden

Another surprisingly FREE stop on our Chicago bucket list is the Chicago Botanic Garden. If you love taking pictures, this is definitely one of the best places for photography in Chicago. Take an educational trip to the Botanic Garden and you’ll make memories that last a lifetime.

Parking at the garden is $25 per vehicle, $30 during holidays. Illinois residents with an EBT card get a discount and only pay $10 for parking, while active duty military and reservists get free parking.

Morton Arboretum

Take a walk through the Children’s Garden and Maze Garden, have lunch at Ginkgo Restaurant overlooking a beautiful lake, and go on a troll hunt. Kids will love all of the outdoor space to explore.

Garfield Park Observatory

If you’re looking for things to do on a rainy day in Chicago, head to the observatory. This indoor botanic garden has beautiful spaces to explore with play areas for children, a koi pond, and over 10 acres of outdoor gardens to explore.

Must See Chicago Attractions

Wrigley Field

Of course you have to see a Cubs game while visiting the Windy City, but Wrigley Field tours are also a must if you have any baseball fans in your family! Learn about the history of this ballpark that has been around for more than 100 years. 

Cloud Gate

Anish Kapoor’s Cloud Gate, most famously known as “The Bean”, is the reason most tourists visit Millennium Park. Take a look during the day and enjoy the clouds, then visit at night for a completely different experience.

John Hancock Center

Some of the most breathtaking views of the city can be seen from the John Hancock Center. It’s worth seeing day and night, so make two visits if you can! If there’s a thrill seeker in the family, be sure to experience TILT. TILT offers a downward facing view of the city from 1,000 feet up. Not for the faint of heart!

Navy Pier

Navy Pier is a favorite amongst tourists for shopping, sightseeing, cruises of Lake Michigan, and more. Take an elegant dining cruise or an upscale private charter of Lake Michigan, finishing the evening off with shopping, a ride on the Ferris wheel, and fireworks (in the summer). Navy Pier has something for everyone.

Millennium Park

Millennium Park has year-round events. Catch a free concert in the summer and go ice skating in the winter. Rent a bike or scooter to save yourself some walking.

The Chicago skyline is beautiful all the time, so don’t forget to snap a photo or two. Millennium Park is one of the best free things to do in Chicago with kids, so don’t miss it!

Maggie Daley Park

This park is another fun thing to do with kids in Chicago. Maggie Daley Park has the best playground downtown, featuring multiple play structures, a climbing wall, and an ice skating ribbon in the winter.

Willis Tower

This is where tourists go for awesome views of the city. If the weather is bad, there won’t be a view, so save it for another day.

Admission can be pricey, but if you have a CityPASS, you can save money.

The tour includes an elevator ride to the 103rd floor where you can take in the 360° views of Chicago. The Skydeck offers a chance to go out on a 4 foot glass box 103 floors above street level, if that sort of thing appeals to you. It’s a great photo op and kids won’t forget it.

Chicago Experiences

If your family is looking for adventure, check out these activities for children in Chicago! And don’t miss these Fun Things to do in Chicago With Teens including escape rooms, Millennium Park, and more!

• Architecture Tour on the River – one of the best ways to see the city from the water and learn about its unique buildings. BOOK IT HERE.
• Seadog Cruise – Older kids will love this high-speed boat ride on Lake Michigan.
• Six Flags Great America Amusement Park – about an hour north of downtown in Gurnee, this is the ultimate place for Chicago family fun and the largest amusement park in the area.
• High tea – Chicago has several awesome options for afternoon tea, including the Drake, Ritz, Peninsula, and Langham hotels.
• Bobby’s Bike Hike – several Chicago bike tours to choose from including food and neighborhood themed. BOOK YOUR TOUR HERE.
• Urban Kayaks – awesome kayak tours along the Chicago River or rent your own.

Chicago Neighborhoods

Pilsen

Pilsen is home to one of the largest Latino communities outside of Mexico. Be sure to eat all of the amazing food, check out the street art, and visit the National Museum of Mexican Art.

Chinatown

Don’t miss dim sum at Triple Crown, Aji Ichiban candy store, the unique architecture of the public library, and bubble tea at Joy Yee Noodle. The Chinese New Year Parade, Autumn Moon Festival, and summer dragon boat races are must-see things to do with kids in Chicago.

Greektown

Be sure to enjoy a meal in one of the restaurants, visit the National Hellenic Museum (with the largest collection of Greek American artifacts in the world), and sample the treats at the Panhellenic Pastry shop.

Chicago Beaches

Did you know that Chicago has 26 miles of lakefront, and beach access is free? Be sure to add one of these to your Chicago bucket list:

• Ohio Street Beach not far from Streeterville, this smaller beach usually has smaller crowds than other beaches.
• Oak Street Beach is located on Lake Shore Drive, so you get a view of the magnificent skyline while swimming. 
• Montrose Beach also on Lake Shore Drive, is the largest beach in Chicago. Montrose Beach has a dog-friendly area where pups can splash in the water and play off leash in a fenced off section of the beach.

Chicago Theatre

Families love Blue Man Group, Broadway in Chicago, and the Marriott Theatre in Lincolnshire (about an hour north of downtown).

Chicago Hiking Trails

• The 606 – this elevated trail was built on an abandoned train track. The trail is less than 6 miles round trip, making it perfect for families.
• Skokie North Shore Sculpture Park – just north of the city, this path features two miles of trails with over 60 sculptures.
• Lakefront Trail – beautiful 18 mile walk along Lake Michigan with the city on the opposite side. Several places to stop along the way, including Navy Pier.

Chicago Food Halls

You can’t fully experience a Chicago family vacation without some tasty grub.

• Time Out Market: With 18 unique restaurants and some of the best chefs in town. This family friendly market is not to be missed.
• French Market: European style marketplace near Ogilvie Transportation center. Don’t miss Happy Lobster and Vanille Patisserie for dessert.
• Latincity: Focus on Latin American street food, with tacos and tortas for the kids and margaritas for the adults.
• Revival Food Hall: All local, fast, casual food. Don’t miss Smoque BBQ and Mindy’s Hot Chocolate for a sweet treat.
• Eataly: Italian market with a grocery, take away, and sit down restaurants, with gelato for dessert.
• Foodlife: Located inside Water Tower Place, this is super convenient for families exploring Michigan Avenue.

Pizza Places in Chicago

I haven’t visited every pizza place in Chicago (yet), but I can vouch for all of the restaurants below.

• Coalfire Pizza – Try the Pistachio Pesto on thin crust.
• Pequod’s Pizzeria – Locals love this pizza joint, but be ready to wait since each pizza cooks for 45 minutes. It’s been called “the best deep dish pizza in the Universe”.
• Lou Malnati’s Pizza – Try the butter crust!

Not a pizza fan? Try the hot dogs! We’re partial to Super Dawg and Portillo’s but there are plenty of hot dogs in Chicago!

Don’t miss Stan’s Donuts, Garrett Popcorn, and the Nutella Cafe. Need more ideas? Don’t miss our list of the best kid-friendly restaurants in Chicago!

Chicago also has some top-notch hotels if you’re looking for a romantic weekend getaway!

You’ll never run out of things to do in Chicago, whether you’re on vacation or you’re a long-time resident. We love all the fun family activities in Chicago and checking things off our Chicago bucket list. 

Travel Tips
Book Your Flights
You can find discounted fares using sites like Momondo or Skyscanner. If you want to keep an eye on discount fares, we suggest signing up for Scott’s Cheap Flights, a daily newsletter with flight sales around the world.

If you travel frequently, consider investing in a Priority Pass for airport lounge access. It’s nice to have a space where you can relax before your flight.

Book Your Accommodation

We regularly use Hotels.com and Expedia.com to find lodging when we travel. It’s a great way to compare vacation rentals, hotels, and resorts.

If your family knows they want to stay in a vacation rental, we recommend looking at VRBO and Plum Guide.

Book Your Transportation

For rental car agencies, try Rentalcars.com. We tend to use Hertz simply for the quality of service.

Book Your Tours and Travel Photos

We regularly used companies like Viator and GetYourGuide to book tours when we travel. Both have great communication and a large variety of activities that work for all ages.

If you’re visiting a city with multiple attractions, be sure to check out a discount pass, such as CityPASS or Go City. Tiqets is another place to purchase tickets for attractions.

Context Travel is another option and they offer more educational based activities. The former teacher in me loves their tours.

One of our favorite things to do annually is take photos with Flytographer. They have photographers around the world and we’ve used them on four separate occasions. This is our favorite travel souvenir.

Don’t Forget Travel Insurance

With the state of travel these days, it’s important to have some type of travel insurance to cover any unforeseen accidents, illnesses, threat or cancellations. We always travel with insurance and would recommend SquareMouth, Travelex, or Medjet as good options. And if you want to compare different insurance options, use Travel Insurance Master to find the best policy for your group.