Chester Holidays from £1,148
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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 31 May 2026
Residence Inn by Marriott St Louis Downtown
Reviewed on 20 May 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
"No pool for kids"
Reviewed on 1 Jun 2026
Baymont by Wyndham Festus
"It looks as if the property is undergoing a renovation. But it was still worthy of the stay. The renovation was not disruptive, or unsightly. Lots of parking close to a lot of different restaurants. Not far off the interstate as well. Would definitely book there again."
Reviewed on 19 May 2026
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
"Very clean. Very good employees. Good breakfast. Great room! Only thing I didn't know was they clean every third night unless you ask. It was fine, just didn't know that. Was given extra towels and all was well. Loved the stay overall and will stay again!!! Better than other hotels nearby!"
Reviewed on 31 May 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.
