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/w1261h711x0y1-96bd53d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago CA $639 per person Apr 14 - Apr 18 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.4/10 Very Good! (2,972 reviews) The staff was the best part, thank you Marcus! This made the stay, at this beautiful hotel. In a world that can seem disconnected, Marcus greeted us with a warm smile, a firm handshake, and gave us the lay of the land. His kind heart was welcoming and engaged. Finding amazing staff like this is hard to come by (coming from a a hospitality background). Our room was spotless and very comfortable. The common areas and hallways were clean and welcoming. I will recommend this hotel! Reviewed on Jan 23, 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago CA $1,312 per person Apr 14 - Apr 18 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned Reviewed on Feb 10, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $1,370 per person Apr 14 - Apr 19 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.2/10 Wonderful! (1,603 reviews) Nice restaurant, attentive staff. Reviewed on Feb 7, 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 $945 per person Apr 14 - Apr 18 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant staff and front desk guys were amazing! Reviewed on Feb 8, 2026 ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile Downtown Chicago CA $929 per person Apr 20 - Apr 24 found 4 hours ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 8.2/10 Very Good! (2,734 reviews) Great stay, parking is confusing though. Reviewed on Feb 10, 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/2026-03-11/2026-03-18/?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/w1261h711x0y1-96bd53d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago CA $537 per person Mar 13 - Mar 16 found 19 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 8.4/10 Very Good! (2,972 reviews) The staff was the best part, thank you Marcus! This made the stay, at this beautiful hotel. In a world that can seem disconnected, Marcus greeted us with a warm smile, a firm handshake, and gave us the lay of the land. His kind heart was welcoming and engaged. Finding amazing staff like this is hard to come by (coming from a a hospitality background). Our room was spotless and very comfortable. The common areas and hallways were clean and welcoming. I will recommend this hotel! Reviewed on Jan 23, 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 $688 per person Mar 13 - Mar 16 found 19 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant staff and front desk guys were amazing! Reviewed on Feb 8, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $910 per person May 7 - May 10 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (1,603 reviews) Nice restaurant, attentive staff. Reviewed on Feb 7, 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/2026-03-11/2026-03-18/?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. ![Fairfield Inn & Suites Chicago Downtown/River North](https://images.trvl-media.com/lodging/6000000/5520000/5511100/5511082/654358ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairfield Inn & Suites Chicago Downtown/River North Downtown Chicago CA $746 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,169 reviews) Clean, comfortable room. Very friendly, helpful staff Reviewed on Feb 10, 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago CA $1,312 per person Apr 14 - Apr 18 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned Reviewed on Feb 10, 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago CA $1,180 per person Apr 15 - Apr 19 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9.2/10 Wonderful! (1,603 reviews) Nice restaurant, attentive staff. Reviewed on Feb 7, 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/2026-03-11/2026-03-18/?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! (2,836 reviews) Clean room, great location, good ambience, excellent breakfast. Reviewed on Feb 10, 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/1000000/10000/8100/8079/7f542141_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! (2,288 reviews) Clean room, nice size. Housekeeping staff in particular were very nice and helpful. No coffee maker in the room, hence 4 vs 5 stars. Reviewed on Feb 10, 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/w3840h2859x0y0-5fc518eb_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! (5,650 reviews) Staff was very warm and welcoming. Breakfast was delicious. The pool was very nice but needs to be shocked every week or after alot of swimmers have been in the pool! Absolutely loved valet, that was definitely a plus. And most of everything you wanna do in Chicago is right next to the hotel!! Reviewed on Feb 11, 2026 [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) [See all 5,624 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