Chicago Kid friendly Vacations

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Discover family-friendly fun in Chicago and beyond

Chicago is renowned for its iconic skyline, Broadway-worthy theater productions, stunning architectural marvels, world-class museums, vibrant art scene, historic monuments, and endless entertainment options. Nestled along the picturesque Lake Michigan, the city offers breathtaking scenery, including picturesque parks, lakefront trails, and beautiful beaches. From shopping on the Magnificent Mile to exploring the Navy Pier, there is no shortage of attractions and activities to keep the entire family entertained. With its diverse and kid-friendly offerings, Chicago is the perfect destination for an unforgettable vacation.

Top Kid friendly vacation packages in Chicago

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago North Shore Deerfield
Omni Chicago Hotel
Sheraton Grand Chicago Riverwalk
Embassy Suites by Hilton Chicago Downtown River North
Silversmith Hotel Chicago Downtown
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3 Night Kid friendly vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Omni Chicago Hotel
Palmer House a Hilton Hotel
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See all available trips from Columbus to Chicago
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4 Night Kid friendly vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Sheraton Grand Chicago Riverwalk
Silversmith Hotel Chicago Downtown
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See all available trips from Columbus to Chicago
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Top reasons for your vacation to Chicago

  • Iconic Skyline: Chicago is renowned for its iconic skyline of towering skyscrapers, offering breathtaking views and photo opportunities.
  • World-class Museums: Explore educational and interactive experiences for children at museums like the Field Museum and the Art Institute of Chicago.
  • Attractions and Entertainment: From Millennium Park to Navy Pier, Chicago offers a wide range of attractions and activities to keep the entire family entertained.
  • Kid-friendly Neighborhoods: Discover family-friendly areas like Navy Pier, the Magnificent Mile, and Lincoln Park, with attractions, interactive experiences, shopping, and outdoor activities.
  • Architectural Marvels: Immerse yourself in the urban charm of Chicago, known as a playground for architectural enthusiasts, with impressive buildings and skyscrapers to admire.

Book a Package and Save Money on Your Chicago Vacation

A travel package combines flights and accommodations, or flights and car rental, making it convenient to book everything together. It saves time by finding everything in one place. You can customize your package to suit your preferences and budget. With Expedia's price and theme filters, you can find the perfect deal for your kid-friendly trip to Chicago and vicinity.

Booking a kid-friendly vacation package in Chicago is the perfect idea for your family trip. With its urban atmosphere, skyscrapers, theaters, museums, and entertainment options, there will be plenty of activities to keep your kids engaged. Explore the city's architecture and art, visit monuments and scenic spots, and enjoy shopping together. Make the most of your vacation with a convenient package.

How to Save Money on a Vacation to Chicago

  • Use public transportation in Chicago, such as the "L" train or buses, instead of taxis or rental cars to save money on local transport.
  • Take advantage of discounted admission days at popular attractions like the Field Museum or Shedd Aquarium.
  • Explore free attractions such as Millennium Park, where kids can enjoy the Crown Fountain and Cloud Gate sculpture.
  • Pack snacks and water bottles to avoid expensive food and drink purchases while sightseeing.
  • Book your accommodation through Expedia's OneKey program to earn points and save money on your stay.
  • Consider purchasing a CityPASS, which offers discounted admission to multiple attractions.
  • Take advantage of free or discounted days offered by museums and attractions for Illinois residents.
  • Check for online deals and coupons for restaurants and activities in Chicago.
  • Visit local parks and playgrounds for free outdoor fun.
  • Consider a visit to the Chicago Children's Museum, which offers free admission on Thursday evenings.

Where to Stay in Chicago

Chicago offers a variety of neighborhoods that are perfect for a kid-friendly vacation. From the vibrant streets of downtown to the family-friendly atmosphere of Lincoln Park, there's something for everyone. Explore the iconic Navy Pier, visit the animals at Lincoln Park Zoo, or enjoy the interactive exhibits at the Museum of Science and Industry.

  • Downtown Chicago: Experience the awe-inspiring skyscrapers, explore museums and theaters, admire the architectural wonders, and enjoy the vibrant art and entertainment scene. Don't miss the scenic river and iconic monuments, making it a perfect destination for a kid-friendly vacation.
  • Near North Side: Marvel at the towering skyscrapers, appreciate the urban architecture, and soak in the picturesque scenery. Explore museums, take a river cruise, indulge in art and shopping, and enjoy dining by the beautiful lake, making it a wonderful choice for a kid-friendly trip.
  • South Loop: Immerse in the rich museum culture, admire the stunning skyscrapers, and enjoy the urban atmosphere. Don't miss the scenic lake, friendly locals, remarkable dining options, beautiful architecture, breathtaking sunsets, and great shopping, making it an ideal destination for a kid-friendly vacation.

Explore the best places to visit in Chicago

Chicago (and vicinity) offers a vibrant and diverse atmosphere for a kid-friendly trip vacation. With its stunning skyline of towering skyscrapers and world-class theaters, the city is a playground for architectural enthusiasts. Museums like the Field Museum and the Art Institute of Chicago provide educational and interactive experiences for children. Families can also explore iconic landmarks such as Millennium Park and Navy Pier, offering entertainment and scenic views. A wide range of shopping options caters to all ages, making Chicago an ideal destination for a memorable family vacation.

  • Six Flags Great America: Experience the thrill of rides and enjoy live music and theater performances at this family-friendly theme park. Explore the beautiful lake and forests, go birdwatching, and indulge in some shopping. Don't forget to try the delicious cheese!
  • Chicago Riverwalk: Immerse yourself in the urban charm of Chicago as you stroll along the river. Admire the impressive architecture and skyscrapers, take a boat ride, and enjoy the scenic views. Dine at waterfront restaurants and witness stunning sunsets.
  • Art Institute of Chicago: Delve into the world of art at this renowned museum. Marvel at the urban skyline from the museum's location, appreciate the architecture, and explore the impressive collection of art and monuments. Enjoy the entertainment and interact with friendly people.

Best months to visit Chicago

Chicago boasts a year-around average temperature of 51.3°F, peaking at 75.9°F in July, its warmest month, and dipping to an average low of 24.8°F in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.


Monthcalendar iconTemperature (Fahrenheit)temperature iconRainfall (mm)rain icon
January24.852.3
February28.849.3
March38.869.1
April50.592.5
May61.0104.9
June71.1103.1
July75.9101.9
August74.1101.3
September66.484.1
October54.382.3
November41.586.9
December28.965.3

FAQs: family vacation packages in Chicago

How can I find the best family vacation packages in Chicago?

For fam-tastic vacation packages in Chicago, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Chicago on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Chicago cost?

You could book your amazing family trip to Chicago just $361. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Chicago family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Chicago?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Chicago family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Chicago landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Chicago family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Chicago family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Chicago Hotels

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4 out of 5
511 North Columbus Drive, Chicago, IL
  • 10 min drive from Wrigley Field
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,652 reviews)
"Our stay was good"

Reviewed on Apr 20, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
  • 12 min drive from Wrigley Field
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,688 reviews)
Birthday Surprise was Egg-cellent!
"Our hotel stay was magnificent. Beauty everywhere I looked. Our room was so cosy and comfortable. All our meals were scrumptious! Staff was very helpful with everything. The hotel and room were spotless. One thing to suggest: softer toilet tissue"

Reviewed on Apr 20, 2025

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
  • 10 min drive from Wrigley Field
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,927 reviews)
"Overall we enjoyed the stay and the property location is close to many restaurants, shops and subway. The complimentary breakfast was great."

Reviewed on Apr 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.