Chester Vacations from $324
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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.
The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn Festus - St Louis South
Price was $397, price is now $330 per person
$330
per person
Feb 15 - Feb 18
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.8/10 Good! (903 reviews)
This place was not very clean. The bed sheets did not feel or smell fresh.
Reviewed on Dec 11, 2025
Discover the most popular places to visit in Chester
Popeye Museum
4.5/5(3 reviews)
You can browse the exhibits at Popeye Museum, a museum with a story of its own, during your travels to Chester. Discover the area's museums and shops.
Fort Kaskaskia
5/5(2 reviews)
Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia.
Kaskaskia Bell
Find out about the history of Chester with a stop at Kaskaskia Bell. Discover the area's museums and shops.
Chester Hotel Deals
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $81 total per night from Dec 21 to Dec 22
$81 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (350 reviews)
The hotel has been declining in recent years but the new management is working to make things better and they are doing a great job. Our room was very comfortable and clean. The staff were very friendly and helpful. It was an enjoyable experience and we will stay here again.
Reviewed on Dec 6, 2025
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Dec 21 to Dec 22
$108 total
Dec 21 - Dec 22
Total with taxes and fees
7.8/10 Good! (884 reviews)
Everything was
Reviewed on Nov 30, 2025
Baymont by Wyndham Festus
1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Dec 16 to Dec 17
$93 total
Dec 16 - Dec 17
Total with taxes and fees
6.8/10 (918 reviews)
Room was clean and comfortable for an overnight stay
Reviewed on Nov 30, 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.
Find the Best Chester Vacation Packages
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 8,600 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Randolph County State Recreation Area, Chester Skating Rink and Marys River Covered Bridge |
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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.
