Chester Holidays from £1,225

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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

Price found within the past 48 hours. Click for updated prices.
Hollywood Casino & Hotel St. Louis
Osceola
Nebraska
The Cheshire
The Knight Center at Washington University

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

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
The price is £70 per night from 11 Jun to 12 Jun
£70
per night
11 Jun - 12 Jun
8.6/10 Excellent! (391 reviews)
Decent hotel to stay at. The breakfast was ok

Reviewed on 9 May 2026

Baymont by Wyndham Chester IL
Baymont by Wyndham Festus

Baymont by Wyndham Festus

3 out of 5
1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
The price is £63 per night from 24 May to 25 May
£63
per night
24 May - 25 May
6.8/10 (962 reviews)
Roaches!!! Toilet and phone didn't work

Reviewed on 14 May 2026

Baymont by Wyndham Festus
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
The price is £86 per night from 21 May to 22 May
£86
per night
21 May - 22 May
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 15 May 2026

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
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. Flight-inclusive packages are ATOL protected.