Title: Chester Vacation Packages & Trips 2026 from CA $933 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6139861.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6139861.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6139861.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) # Chester 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 Chester Vacation With a Chester vacation package, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before you depart, so you can spend more time experiencing this fantastic city. A trip to Chester is a wonderful opportunity to do a bit of sightseeing. Be sure to stop by well-known attractions like [Chester Skating Rink](https://www.expedia.ca/Chester-Skating-Rink-Chester.d6183790.Vacation-Attraction), [Popeye Museum](https://www.expedia.ca/Popeye-Museum-Chester.d553248621532655787.Vacation-Attraction) and [Marys River Covered Bridge](https://www.expedia.ca/Marys-River-Covered-Bridge-Chester.d6183795.Vacation-Attraction). Expedia is here to help you escape the everyday. Tailor your vacation to Chester to suit your travel style, whatever that may look like. ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel CA $933 per person Apr 10 - Apr 15 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 9.2/10 Wonderful! (1,600 reviews) Room was clean and big with a separate sitting area. We would definitely stay there again . Reviewed on Jan 21, 2026 ![Hilton Garden Inn Chesterfield](https://images.trvl-media.com/lodging/1000000/300000/297100/297075/c23cebe0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chesterfield CA $1,040 per person Apr 10 - Apr 15 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8.2/10 Very Good! (779 reviews) Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again. Reviewed on Dec 22, 2025 ![Hermann Grain Bins BNB ](https://images.trvl-media.com/lodging/117000000/116770000/116761300/116761277/27846aee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hermann Grain Bins BNB CA $1,818 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YYZ) to St. Louis (STL) 2/10 (1 review) ![The Cheshire](https://images.trvl-media.com/lodging/1000000/30000/26100/26061/b6ec06de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cheshire CA $1,170 per person Apr 10 - Apr 15 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8.6/10 Excellent! (1,002 reviews) There was a bolier breakdown so there was no hot water on the property the last night of our stay, making a shower rather unpleasant. There were some obsrved maintenance issues in the fitness room: dumbbell sets over 35 lb. were missing, there were no towels or wipes to wipe down equipment, the trash can was overflowing in the men’s restroom, with trash on the floor, and there was little to no bottled water available the last 2 days of the stay. The breakfast was good as always, with berries every day, and the personnel were generally responsive to our requests. Reviewed on Jan 20, 2026 ![Crowne Plaza St. Louis Airport by IHG](https://images.trvl-media.com/lodging/1000000/10000/3100/3010/45ba14e8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crowne Plaza St. Louis Airport by IHG CA $977 per person Apr 10 - Apr 15 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8/10 Very Good! (1,002 reviews) I was there for the fantail show. Everything was fantastic! Thank you so much! Reviewed on Jan 14, 2026 ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Baymont by Wyndham Chester IL](https://images.trvl-media.com/lodging/1000000/10000/1700/1699/19091438_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Chester IL 2150 State Street Chester IL Fully refundableReserve now, pay when you stay CA $96 CA $106 total Feb 6 - Feb 7 includes taxes & fees 8.4/10 Very Good! (353 reviews) The hotel has been declining in recent years but the new management is working to make things better and they are doing a great job. Our room was very comfortable and clean. The staff were very friendly and helpful. It was an enjoyable experience and we will stay here again. Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F02%2F2026&endDate=07%2F02%2F2026&selected=1699&PinnedHotelID=1699&HadPinnedHotel=true®ionId=6139861) ![La Quinta Inn & Suites by Wyndham Festus - St. Louis South](https://images.trvl-media.com/lodging/1000000/50000/42200/42120/1887aa70_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Festus - St. Louis South 1001 Veterans Blvd Festus MO Fully refundableReserve now, pay when you stay CA $128 CA $147 total Jan 25 - Jan 26 includes taxes & fees 7.8/10 Good! (906 reviews) Clean room Reviewed on Jan 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=42120&PinnedHotelID=42120&HadPinnedHotel=true®ionId=6139861) ### Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy 7555 State Hwy Y French Village MO CA $123 CA $192 total Jan 26 - Jan 27 includes taxes & fees 9.8/10 Exceptional! (48 reviews) I had a great time with my mom there! Reviewed on Jan 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=110550817&PinnedHotelID=110550817&HadPinnedHotel=true®ionId=6139861) [See all 161 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F01%2F2026&endDate=24%2F01%2F2026®ionId=6139861) 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