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.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was CA $1,255, price is now CA $1,054 per person
CA $1,054
per person
Jun 5 - Jun 8
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.8/10 Excellent! (1,056 reviews)
The property was beautiful and unique. The food was a disappointment. Unfortunately it was just too greasy for us.
Reviewed on Mar 6, 2026
The Wildwood Hotel
Price was CA $1,967, price is now CA $1,240 per person
CA $1,240
per person
Apr 10 - Apr 17
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,626 reviews)
We stayed for 1 night, overall good experience. The pool water was pretty cold and the hot tub is small (max occupancy 2). I was a little disappointed in the continental breakfast. Make your own waffles, cereal, and assorted breads. Wished for a larger selection and ready-made hot foods.
Reviewed on Mar 8, 2026
Hampton Inn St. Charles St. Peters
Price was CA $1,537, price is now CA $1,311 per person
CA $1,311
per person
Apr 10 - Apr 17
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8/10 Very Good! (1,002 reviews)
Soaps/lotion in bathroom were low or empty upon check in. Too heavy on the scent of cleaning solution, gave me a headache. Dark roast coffee was weak.
Reviewed on Mar 3, 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 $111 per night from Mar 15 to Mar 16
CA $111
CA $123 total
Mar 15 - Mar 16
includes taxes & fees
8.6/10 Excellent! (366 reviews)
Ok
Reviewed on Mar 4, 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 $152 per night from Apr 5 to Apr 6
CA $152
CA $174 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (923 reviews)
The room was the cleanest that I have ever stayed in, in my life, totally spotless! The breakfast was very good, with alot of choices available!
Reviewed on Mar 7, 2026
Holiday Inn Express & Suites Perryville by IHG
2020 Jefferson St Perryville MO
Fully refundable
The price is CA $140 per night from Apr 5 to Apr 6
CA $140
CA $160 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (563 reviews)
Room was great, front desk was professional but friendly. Breakfast was excellent. Spotless — both room and lobby.
Reviewed on Feb 24, 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.
