Chester Vacation Packages
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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.
River City Casino & Hotel
Price was CA $832, price is now CA $744 per person
CA $744
per person
Jun 4 - Jun 6
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,521 reviews)
The room was clean and well appointed with a large bathroom and great shower. Comfortable beds. Staff friendly and helpful, especially Emani at the front desk. Highly recommended.
Reviewed on Apr 24, 2026
DoubleTree by Hilton Hotel St. Louis - Chesterfield
Price was CA $1,186, price is now CA $1,042 per person
CA $1,042
per person
Jun 4 - Jun 6
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Clean room, friendly & helpful staff, cook prepared omelette breakfast was yumyum. Really enjoyed our stay!
Reviewed on Apr 4, 2026
The Knight Center at Washington University
Price was CA $931, price is now CA $839 per person
CA $839
per person
Jun 4 - Jun 6
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.4/10 Exceptional! (523 reviews)
Uneven front desk team. Some incredibly caring & friendly. Some downright rude. For $400/night, you are paying for the convenience of being on campus. Amenities basic.
Reviewed on Apr 19, 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 Apr 26 to Apr 27
CA $102
CA $114 total
Apr 26 - Apr 27
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 Apr 28 to Apr 29
CA $127
CA $145 total
Apr 28 - Apr 29
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
