Title: Cherry Vacation Packages & Trips 2026 from CA $643 | Expedia.ca [Hotels in Cherry](https://expedia.ca/Cherry-Hotels.d553248634983184518.Travel-Guide-Hotels)[Vacation Rentals in Cherry](https://expedia.ca/Cherry-Vacation-Rentals.d553248634983184518.Travel-Guide-VacationRentals)[Cherry Car Rentals](https://expedia.ca/Car-Rentals-In-Cherry.d553248634983184518.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Cherry Vacation Packages ## 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 #### Your Cherry Vacation Entertainment, food, art and more … There's so much to immerse yourself in with a Cherry vacation package. And with the ability to customize your city adventure, you know it'll be one that's tough to forget. Can't wait to sightsee but not sure where to begin? Any trip to Cherry should include [Spring Creek Golf Course](https://www.expedia.ca/Spring-Creek-Golf-Course-Spring-Valley.d6187192.Vacation-Attraction). Whoever you're taking a break with and whether your budget is big or small, your dream Cherry vacation is just clicks away with Expedia. ## Top Cherry Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Aloft Chicago Downtown River North](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aloft Chicago Downtown River North Downtown Chicago CA $643 per person Apr 24 - Apr 27 found 19 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,159 reviews) Staff was great but next to fire station. Beware very noisy if staying city view Reviewed on Feb 8, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,720 per person Apr 2 - Apr 6 found 7 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $1,088 per person May 5 - May 10 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 2026 ![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/43aaf412_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Arista CA $925 per person Apr 14 - Apr 19 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,003 reviews) the room was good the sheets were clean amenities were nice parking was available staff was very courteous gave me water bottle when I asked Reviewed on Jan 24, 2026 ![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 $858 per person Mar 19 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Clean room…. Although we paid $55.00 for breakfast when we booked our reservation only to be given a $32.00 voucher for breakfast. BAD FORM!!!! Reviewed on Feb 11, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248634983184518) ## Ready to book your vacation to Cherry? Choose your dates ## Cherry Hotel Deals ![Grand Bear Resort at Starved Rock](https://images.trvl-media.com/lodging/2000000/1510000/1500900/1500830/c6b13292_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Bear Resort at Starved Rock 2643 IL-178 Utica IL Fully refundableReserve now, pay when you stay CA $151 CA $173 total Feb 17 - Feb 18 includes taxes & fees 7.2/10 Good! (1,001 reviews) Really great value, no problems with the room. Helpful staff, lots of families were having fun in the waterpark. It could use a few updates, but I'm not overly picky about stuff like that. Clean and met all needs. Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=1500830&PinnedHotelID=1500830&HadPinnedHotel=true®ionId=553248634983184518) ![Days Inn by Wyndham Oglesby/ Starved Rock](https://images.trvl-media.com/lodging/1000000/30000/21100/21068/3d45dbc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Oglesby/ Starved Rock 120 N Lewis Ave Oglesby IL Fully refundableReserve now, pay when you stay CA $109 CA $120 total Feb 26 - Feb 27 includes taxes & fees 8/10 Very Good! (1,000 reviews) Th room was clean but there were a couple stains on the sheets but I’m pretty sure they were clean. You could see hair on the mattress through the sheets. See pics. I slept good. Basic room. Bed was comfy. Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=21068&PinnedHotelID=21068&HadPinnedHotel=true®ionId=553248634983184518) ![La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park](https://images.trvl-media.com/lodging/1000000/160000/151200/151149/7d0cb463_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park 4389 Venture Dr Peru IL Fully refundableReserve now, pay when you stay CA $126 CA $142 total Mar 1 - Mar 2 includes taxes & fees 7.6/10 Good! (173 reviews) Room was clean, staff was friendly & curtious, hot tub was exactly what i needed, pool was way too cold for me, lol, pool room was like being in a giant sauna, which gave a vet relaxing feel. Breakfast was a little on the lacking side but the coffee was good! Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=151149&PinnedHotelID=151149&HadPinnedHotel=true®ionId=553248634983184518) [See all 170 properties in Cherry](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=553248634983184518) 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. ![](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) ## Explore a world of travel with Expedia \* 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