Title: Chesterfield Vacation Packages & Trips 2026 from CA $881 | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d553248634983592733.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d553248634983592733.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d553248634983592733.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) # Chesterfield 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 ## Top Chesterfield Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel Indigo St Louis - Central West End by IHG](https://images.trvl-media.com/lodging/1000000/30000/22100/22068/bd89b9ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo St Louis - Central West End by IHG Central West End CA $881 per person Apr 24 - Apr 28 found 4 hours ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8.2/10 Very Good! (1,000 reviews) Just a really cool place. One of the cleanest hotels I've stayed in i St Louis. Everyone was really friendly. Reviewed on Feb 6, 2026 ![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 $1,197 per person Apr 24 - Apr 28 found 4 hours ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 9.2/10 Wonderful! (1,600 reviews) Clean room and easy parking. Reviewed on Feb 2, 2026 ![Hotel Saint Louis, Autograph Collection](https://images.trvl-media.com/lodging/28000000/27480000/27478600/27478599/8a12cc18_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Saint Louis, Autograph Collection Downtown St. Louis CA $1,349 per person Apr 24 - Apr 28 found 4 hours ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8.8/10 Excellent! (458 reviews) Property and room was really nice. I will be staying here in the future Reviewed on Nov 25, 2025 ![Hilton Garden Inn St. Louis/O'Fallon MO](https://images.trvl-media.com/lodging/1000000/930000/921500/921433/e9a336ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn St. Louis/O'Fallon MO CA $1,132 per person Apr 24 - Apr 28 found 4 hours ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 8.8/10 Excellent! (705 reviews) The front desk staff was outstanding. Great location for us Reviewed on Feb 3, 2026 ![The Knight Center at Washington University](https://images.trvl-media.com/lodging/39000000/38720000/38711900/38711810/302445f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Knight Center at Washington University CA $988 per person Apr 24 - Apr 28 found 4 hours ago Roundtrip non-stop flight included Calgary (YYC) to St. Louis (STL) 9.4/10 Exceptional! (425 reviews) Very friendly and helpful front desk staff and restaurant staff. Lovely experience! Reviewed on Feb 4, 2026 ## Ready to book your vacation to Chesterfield? Choose your dates ## Chesterfield Hotel Deals ![Super 8 by Wyndham Staunton](https://images.trvl-media.com/lodging/1000000/70000/62400/62339/a2a3bf94_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Staunton 1527 Herman Rd Staunton IL Fully refundableReserve now, pay when you stay CA $88 CA $97 total Feb 17 - Feb 18 includes taxes & fees 8.4/10 Very Good! (768 reviews) Comfortable bed, quiet room, courteous staff, convenient location. Price was a nice deal for the king suite. This was a last minute booking for visiting family nearby. Smooth check-in, easy checkout. Reviewed on Jan 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=62339&PinnedHotelID=62339&HadPinnedHotel=true®ionId=553248634983592733) ![ Memorable Family experiences at The Castle of Palmyra. ](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654469/739c0b18_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Memorable Family experiences at The Castle of Palmyra. Palmyra IL 9.8/10 Exceptional! (109 reviews) First of all, the property is lovely. Debbi is an amazing property manager and extremely helpful! The kitchen is outfitted with everything you could imagine you might need. Lots of places to gather and just be together. Reviewed on Jan 6, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=33654469&PinnedHotelID=33654469&HadPinnedHotel=true®ionId=553248634983592733) [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=33654469&PinnedHotelID=33654469&HadPinnedHotel=true®ionId=553248634983592733) ![Super 8 by Wyndham Jerseyville](https://images.trvl-media.com/lodging/1000000/450000/440500/440446/8d67e6ab_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Jerseyville 1303 State Highway 109 Jerseyville IL Fully refundableReserve now, pay when you stay CA $108 CA $120 total Feb 22 - Feb 23 includes taxes & fees 7.8/10 Good! (335 reviews) staff Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=440446&PinnedHotelID=440446&HadPinnedHotel=true®ionId=553248634983592733) [See all 25 properties in Chesterfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%2F2026®ionId=553248634983592733) 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