Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Your Chester Holiday

Our holiday packages to Chester provide endless opportunities to immerse yourself in new sights, sounds and experiences. And with all your travel plans taken care of, you'll be free to enjoy your city escape to the fullest. You'll want to take in some sights during your trip to Chester. Carve out some time for major attractions such as Popeye Museum, Chester Skating Rink and Marys River Covered Bridge. Check out Expedia's wide range of travel options and start organising your ultimate holiday to Chester now.

Chester Holiday

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 Marys River Covered Bridge

Our pick of the best Chester Hotel Deals

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 AU$121 per night from 13 Aug to 14 Aug
AU$121
13 Aug - 14 Aug
includes taxes & fees
8.4/10 Very good! (408 reviews)
"Did not like the check out process"

Reviewed on 21 July 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 AU$165 per night from 26 July to 27 July
AU$165
26 July - 27 July
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Clean room, lobby smells like cigarettes. Booked through Expedia and paid Expedia. La Quinta also charged my card for the same stay"

Reviewed on 21 July 2026

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
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 AU$103 per night from 16 Aug to 17 Aug
AU$103
16 Aug - 17 Aug
includes taxes & fees
6.8/10 (996 reviews)
"Would stay again for longer time very close to food options"

Reviewed on 22 July 2026

Baymont by Wyndham Festus
See all 170 properties in Chester
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Chester attractions

Fort Kaskaskia

9.6/10 (4 reviews)
Explore the earthen remains of this 18th-century French fortification, once protecting Illinois' first capital. Savour panoramic Mississippi River views while discovering colonial history at the interpretive overlook.
See properties

Frequently asked questions

How much does a Chester holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you'd like to score a cheap Chester holiday package, consider visiting in December, January and February. You'll usually find lower rates on flights and accommodation during these months — ideal for travellers wishing to save money.
How many days is enough for Chester?
With a well-organised itinerary, you can easily tick off the most popular Chester attractions in a few days. But if you'd like to discover hidden gems or go on day trips, consider booking your Chester holiday for longer.
Is it worth booking a holiday package to Chester?
Chester is a good holiday destination with attractions like Elzie C. Segar Memorial Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Chester holiday promises a good time for everyone.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Chester package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester escape underway.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chester?
If you're planning a spur-of-the-moment Chester adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to Chester.
  3. Decide how long to go away for: Now that you're more familiar with Chester, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalised Chester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.