Title: Kid friendly Vacations in West Side 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Kid friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 West Side Price found within the past 48 hours. Click for updated prices. ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $609 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) I wish that all the staff was more accommodating! some of them were some were not! Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CNwUkFUJBUDEU6RCyVU7aMpzofSxQsUma6rGQpv_eDXd) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $821 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CNwUkFUJBUDEU6RCyVU7aMoFdBXUxLPLOQZAcgqUGjz8) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $827 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Clean room, friendly staff, great location and within walking distance from all shops! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CNwUkFUJBUDEU6RCyVU7aMrUT9b3G3v8zsgZOPitNNAj) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $860 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Perfect location and atmosphere Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CNwUkFUJBUDEU6RCyVU7aMqiGwC_NZIzrWoSs8Ptm645) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $649 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,142 reviews) Absolutely loved this place.... views were great, staff was great, atmosphere was great! One of my most favorite places to stay. Reviewed on Oct 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=57651125&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CNwUkFUJBUDEU6RCyVU7aMpISwDFjSlNxUeemhlGKCS3) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,066 per person Dec 28 - Dec 31 found 18 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=QpLfFRqLVDnisD62S_OWRqme0LBWW_NlQp0_F4ZrOtBGhsHRKh0TeYyMNlweVyeo) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,300 per person Dec 29 - Jan 2 found 19 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=QpLfFRqLVDnisD62S_OWRk3-lAEb7n-KdQNQn4IPdmZ4FvcP-9V8h_I1v9eZ53pB) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,471 per person Dec 24 - Dec 28 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-28/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=i-scMYON3kKiMGO8VUu8-AR7HhUlgYEmk8P_7dxQK96EsGMMwvp7EPibFJKUKVsw) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,008 per person Dec 28 - Dec 31 found 18 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRqme0LBWW_NlQp0_F4ZrOtDG4KsmXsxr_znYGMfJyBOr) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,181 per person Nov 8 - Nov 11 found 3 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-11/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=inO400m4vNsdT9Pocg7D8EKES8QeUCRNBCza38nfe65mZOJv-1sw7i_3vf4F9Tf2) ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,066 per person Dec 28 - Dec 31 found 18 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRqme0LBWW_NlQp0_F4ZrOtBGhsHRKh0TeYyMNlweVyeo) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $706 per person Dec 29 - Jan 2 found 19 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRpQL3R3aZX-1Vdp2C9KRAn4WR4WzTu2_s9d5PeMT5Gqh) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $780 per person Nov 12 - Nov 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (2,765 reviews) The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&dealMarker=4KHtf_28eG-jw6YvmuAD3-hgJ6tiHGVnDAvDc1KKTfF1or96vJoTFK8Cy7y3PEA7) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,310 per person Nov 12 - Nov 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=4KHtf_28eG-jw6YvmuAD3zyFKGwXkl6MtSwEkabZoO8JGLhJHwq7_jY3nBkJ4vPe) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in West Side with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in West Side 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 West Side. #### Are there cheap family vacations to West Side? 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 West Side 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 West Side? Yes, you'll find plenty of all-inclusive family vacation packages for West Side. 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 West Side, 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 West Side or something a bit more relaxed. #### Can I find luxury family vacations in West Side? If you're looking for a luxury family vacation to West Side, 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 West Side. #### 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 West Side 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. ## 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 > - 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[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 West Side](https://expedia.ca/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[West Side Hotels](https://expedia.ca/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[West Side Vacation Rentals](https://expedia.ca/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[West Side Car Rentals](https://expedia.ca/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[West Side Vacations](https://expedia.ca/West-Side.d553248635976475400.Destination-Travel-Guides)[Things to do in West Side](https://expedia.ca/Things-To-Do-In-West-Side.d553248635976475400.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. 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