Chester Holidays from £944
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Your Chester Holiday
With a Chester holiday 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 holiday to Chester to suit your travel style, whatever that may look like.
Top Chester Flight + Hotel Deals
The Cheshire
Reviewed on 6 Feb 2026
Hotel Indigo St. Louis - Downtown by IHG
Reviewed on 2 Feb 2026
DoubleTree by Hilton Hotel St. Louis - Chesterfield
Reviewed on 10 Feb 2026
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 8,600 |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Randolph County State Recreation Area, Chester Skating Rink and Elzie C. Segar Memorial Park |
Top hotels in Chester
Baymont by Wyndham Chester IL
Very clean hotel and the beds were comfortable. Will definitely stay there again. Very economical!
Reviewed on 20 Jan 2026
Baymont by Wyndham Festus
Room was good and staff was helpful and friendly
Reviewed on 29 Dec 2025
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Great staff, room was clean and comfortable. Clean and fully stocked breakfast.
Reviewed on 31 Jan 2026
Popular places to visit
Kaskaskia Bell
Find out about the history of Chester when you take a trip to Kaskaskia Bell. Discover the area's museums and shops.
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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. Flight-inclusive packages are ATOL protected.
