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.
Hilton Pennywell St. Louis at the Arch
Downtown St. Louis
Price was CA $1,368, price is now CA $1,130 per person
CA $1,130
per person
Jul 31 - Aug 3
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,048 reviews)
Clean rooms and comfortable lounge with friendly staff
Reviewed on May 14, 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 May 31 to Jun 1
CA $111
CA $123 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (391 reviews)
Decent hotel to stay at. The breakfast was ok
Reviewed on May 9, 2026
Baymont by Wyndham Festus
1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jun 14 to Jun 15
CA $105
CA $120 total
Jun 14 - Jun 15
includes taxes & fees
6.8/10 (962 reviews)
Roaches!!! Toilet and phone didn't work
Reviewed on May 14, 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 $139 per night from May 18 to May 19
CA $139
CA $159 total
May 18 - May 19
includes taxes & fees
8/10 Very Good! (980 reviews)
I stayed for 2 nights, arriving really late the first night and was greeted right away by the night manager on duty. My dog and I had a great stay, the room was clean and all amenities were just fine. The breakfast was a great surprise and really enjoyed it. Would definitely stay again.
Reviewed on May 15, 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.
