Title: Kid friendly Vacations in Chicago 2026 | Expedia.ca ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Kid friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Kid friendly hotel deals in Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago CA $646 per person Apr 22 - Apr 24 found 16 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (3,039 reviews) Amazing location literally everything is close by and you could walk Reviewed on Mar 16, 2026 ![Sheraton Grand Chicago Riverwalk](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Grand Chicago Riverwalk Downtown Chicago CA $923 per person May 22 - May 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,614 reviews) The view of the Chicago river from my room was absolutely perfect. I loved coming back to my room to see the river and city lights view. There is a Whole Foods very close by which makes it easy to pick up snacks and drinks. Staff were all friendly and helpful! The hotel in general is a great point that’s close to city attractions & very walkable. The only downside I would point out is the cleanliness of the rooms & the food quality. When I checked in, there was trash in a trash can from the previous stay. I had ordered a shrimp po boy from room service, expecting real whole shrimp as shown in the menu photo. However, the sandwich was made with popcorn shrimp which just isn’t the same taste or quality. Overall, I would visit again but would look elsewhere for late night eats. Reviewed on Mar 17, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/93676f62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $1,272 per person May 22 - May 26 found 10 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,710 reviews) Everything at the Omni was amazing!! Reviewed on Mar 20, 2026 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago CA $1,039 per person Apr 26 - Apr 30 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 8.6/10 Excellent! (2,675 reviews) This hotel is awesome for visiting Chicago. The staff were consistently attentive, respectful and helpful with suggestions. The hotel room was clean and the view we had was fantastic. The pool and hot tub were relaxing — easy to access and get fresh towels. The only minor criticism was that the hotel is an older building and shows some wear and tear — if I owned it, I’d invest in new flooring because the old carpet is super gross. That said, for what we paid and what we got, we are extremely satisfied and glad we stayed at the Hilton, and will likely stay there again! Reviewed on Mar 19, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago CA $611 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 8.6/10 Excellent! (3,039 reviews) Amazing location literally everything is close by and you could walk Reviewed on Mar 16, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/93676f62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $1,388 per person Jun 5 - Jun 8 found 4 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,710 reviews) Everything at the Omni was amazing!! Reviewed on Mar 20, 2026 ![Sheraton Grand Chicago Riverwalk](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Grand Chicago Riverwalk Downtown Chicago CA $923 per person May 22 - May 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,614 reviews) The view of the Chicago river from my room was absolutely perfect. I loved coming back to my room to see the river and city lights view. There is a Whole Foods very close by which makes it easy to pick up snacks and drinks. Staff were all friendly and helpful! The hotel in general is a great point that’s close to city attractions & very walkable. The only downside I would point out is the cleanliness of the rooms & the food quality. When I checked in, there was trash in a trash can from the previous stay. I had ordered a shrimp po boy from room service, expecting real whole shrimp as shown in the menu photo. However, the sandwich was made with popcorn shrimp which just isn’t the same taste or quality. Overall, I would visit again but would look elsewhere for late night eats. Reviewed on Mar 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Comfort Suites Oakbrook Terrace near Oakbrook Center](https://images.trvl-media.com/lodging/1000000/20000/11400/11309/17a7867e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Oakbrook Terrace near Oakbrook Center York Center CA $578 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7.8/10 Good! (1,000 reviews) Staff was great and polite. Breakfast was meh, but it got the job done. Reviewed on Mar 18, 2026 ![Residence Inn by Marriott Chicago Downtown / River North](https://images.trvl-media.com/lodging/2000000/1770000/1763600/1763534/bc137fa6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residence Inn by Marriott Chicago Downtown / River North Downtown Chicago CA $805 per person Apr 23 - Apr 27 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,040 reviews) This is our go-to stop whenever we visit chicago. We find that many of the places we frequent are nearby. It's so easy, you can leave your car in the garage and go. The only drawback or downside is their breakfasts. They could up their game. Otherwise, love the place and will continue to return. Reviewed on Mar 20, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/93676f62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $1,272 per person May 22 - May 26 found 10 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,710 reviews) Everything at the Omni was amazing!! Reviewed on Mar 20, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in Chicago with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in Chicago are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. #### How can I find the best family-friendly vacations? Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Chicago. #### Are there cheap family vacations to Chicago? Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. #### When should I book family-friendly vacation packages? The right time to book family-friendly vacation packages in Chicago depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. #### Can I book an all-inclusive family vacation in Chicago? Yes, you'll find plenty of all-inclusive family vacation packages for Chicago. To see what's available, just select the all-inclusive filter on your search. #### How can I book the best family activity vacation? If you're looking to make the most out of the available activities in Chicago, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Chicago or something a bit more relaxed. #### Can I find luxury family vacations in Chicago? If you're looking for a luxury family vacation to Chicago, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. #### How can I search for family vacation deals? Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Chicago. #### Can I book a family vacation package that is fully refundable? If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Chicago are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking. #### Why should I book my family trip with Expedia? When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings. ## Kid friendly Hotels in Chicago ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile 511 North Columbus Drive Chicago IL - 10 min drive from Wrigley Field Book a stay at this 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! (2,796 reviews) Rooms were spacious. Hotel was very clean and conveniently located in walking distance to top attractions in Chicago. Family friendly. Will definitely stay here again. Reviewed on Mar 20, 2026 [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL - 12 min drive from Wrigley Field Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,328 reviews) Very nice hotel in the heart of downtown! Reviewed on Mar 20, 2026 [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL - 10 min drive from Wrigley Field Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ... 8.6/10 Excellent! (5,757 reviews) Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again. Reviewed on Mar 20, 2026 [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) [See all 5,558 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Kid friendly Vacation Destinations > - [Family vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/190/United-Kingdom) > - [Family vacations in Bali ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/602651/Bali) > - [Family vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/2680/Ontario) > - [Family vacations in France ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/59/France) > - [Family vacations in Spain ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/166/Spain) > - [Family vacations in Paris ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/179898/Paris) > - [Family vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/174/Switzerland) > - [Family vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/86/Italy) > - [Family vacations in South Africa ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/165/South-Africa) > - [Family vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/1418/Victoria) > - [Family vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/11219/Scotland) > - [Family vacations in Alaska ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/203/Alaska) > - [Family vacations in Bournemouth ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/654/Bournemouth) > - [Family vacations in Philippines ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/145/Philippines) > - [Family vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/6047194/Tenerife) > - [Family vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/10/Australia) > - [Family vacations in Egypt ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/52/Egypt) > - [Family vacations in Tuscany ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/601686/Tuscany) > - [Family vacations in Panama ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/142/Panama) ## More Vacations Ideas [Flights to Chicago ](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Vacation Rentals ](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[ Chicago Car Rentals ](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[ Chicago Vacations ](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[ Things to do in Chicago ](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app