Chester Holidays from £1,139

Book a Hotel + Flight or Car together to unlock savings

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.
The Cheshire
 The Royal Sonesta Chase Park Plaza St. Louis
The Wildwood Hotel
Hilton Garden Inn Chesterfield
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

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 £61 per night from 26 Apr to 27 Apr
£61
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (383 reviews)
Shops and pool were not of our interest

Reviewed on 9 Apr 2026

Baymont by Wyndham Chester IL
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 £78 per night from 28 Apr to 29 Apr
£78
28 Apr - 29 Apr
includes taxes & fees
8/10 Very Good! (959 reviews)
Not satisfied with the cleanliness, comfort or condition of our room

Reviewed on 13 Apr 2026

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St Perryville MO
Fully refundable
The price is £85 per night from 23 Apr to 24 Apr
£85
23 Apr - 24 Apr
includes taxes & fees
9.2/10 Wonderful! (578 reviews)
Stay was amazing. Beds were very comfortable, rooms were super clean and staff was very helpful.

Reviewed on 10 Apr 2026

Holiday Inn Express & Suites Perryville by IHG
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.

Popular places to visit

Explore a world of travel with Expedia

* 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.