Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, Popeye Museum and Marys River Covered Bridge. 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
Price was CA $1,070, price is now CA $806 per person
CA $806
per person
Jun 4 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,624 reviews)
A very nice little place to say breakfast was really good too combination of hot and cold choices. Everybody was very friendly and helpful that worked there.
Reviewed on Apr 24, 2026
Hilton Pennywell St. Louis at the Arch
Downtown St. Louis
Price was CA $1,779, price is now CA $1,495 per person
CA $1,495
per person
Jun 1 - Jun 5
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.8/10 Excellent! (1,030 reviews)
Dated property, no closet, nice bed.
Reviewed on Apr 24, 2026
The Westin St. Louis
Downtown St. Louis
Price was CA $1,493, price is now CA $1,279 per person
CA $1,279
per person
Jun 1 - Jun 5
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.6/10 Excellent! (1,009 reviews)
Mold on bathroom parking expensive when there is a cheaper lot not far but a solid 3.5 compared to others
Reviewed on Apr 24, 2026
Hilton St. Louis Airport
Woodson Terrace
Price was CA $1,221, price is now CA $1,049 per person
CA $1,049
per person
Jun 1 - Jun 5
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
7.6/10 Good! (1,012 reviews)
Great breakfast, the room was comfortable nice bed. It's an older hotel but it's nicely located close to the golf course for a college event. Ate downtown by the river at Toni's
Reviewed on Apr 13, 2026
Chester Hotel Deals
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from May 17 to May 18
CA $102
CA $113 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (386 reviews)
We had a very nice stay. The hotel is clean and the staff was very friendly. My only complaint is the breakfast. They do have a waffle maker but the batter had a funny taste and the available muffins were hard.
Reviewed on Apr 17, 2026
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 10 to May 11
CA $127
CA $145 total
May 10 - May 11
includes taxes & fees
8/10 Very Good! (969 reviews)
Close to stores and our final destination.
Reviewed on Apr 21, 2026
Holiday Inn Express & Suites Perryville by IHG
2020 Jefferson St Perryville MO
Fully refundable
The price is CA $138 per night from May 3 to May 4
CA $138
CA $158 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (580 reviews)
No
Reviewed on Apr 22, 2026
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.
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.
