
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.




Lighthouse Inn & Suites
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
9/10 Wonderful! (11 reviews)
Location is excellent! Close to historic downtown but far enough away to be quiet and peaceful! Very clean and decor is wonderful!
Reviewed on Jul. 6, 2025

Best Western On The River
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.6/10 Excellent! (1,003 reviews)
The man at the desk when I checked was very nice & helpful with answers to my questions . The breakfast was ok , the food could be hotter & change the menu more than just sausage links or patties , or add waffles or something different .
Reviewed on Aug. 2, 2025
Chester Hotel Deals

Baymont by Wyndham Chester IL
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 14 to Aug 15
CA $119
CA $132 total
Aug 14 - Aug 15
includes taxes & fees
8.6/10 Excellent! (324 reviews)
"Breakfast was not great some stale muffins and only a few yogurt one and a little eggs and no sausage"
Reviewed on Aug. 2, 2025

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 $150 per night from Aug 31 to Sep 1
CA $150
CA $172 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (826 reviews)
"Truly amazed by the speed of check-in. The clerk on duty had her paperwork all ready, spread out on a desk. She seemed to guess which guest I was and just handed over the document to initial. Perfect efficiency! Also, she was pleasant. The lobby, stairs and hallways had been recently upgraded. Room ..."
Reviewed on Jul. 21, 2025

Holiday Inn Express & Suites Perryville by IHG
2020 Jefferson St, Perryville, MO
Fully refundable
The price is CA $152 per night from Aug 23 to Aug 24
CA $152
CA $174 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (493 reviews)
"Super nice staff. Our room smelled so nice and clean. Breakfast was very good too!"
Reviewed on Aug. 1, 2025
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.