Chester Holidays

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Chester Holiday

Our pick of the best Chester Hotel Deals

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
NZ$137
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (413 reviews)
"Great rooms and extra clean. My go to place ti stay when in the area."

Reviewed on 5 Aug 2026

Baymont by Wyndham Chester IL
Baymont by Wyndham Festus

Baymont by Wyndham Festus

1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
NZ$124
26 Aug - 27 Aug
includes taxes & fees
6.8/10 (1,003 reviews)
"Dated and a damp smell to it in the room"

Reviewed on 10 Aug 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

1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
NZ$196
12 Aug - 13 Aug
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Towel left in room from previous guest.... floor felt dirty on my barefoot. And the pool was green... Breakfast was disappointing. Biscuits were dried out the gravy was burnt there was no sausage. I've stayed in many LaQuinta hotels and this was the worst stay ive ever had. We chose this location ..."

Reviewed on 9 Aug 2026

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
See all 169 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.

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.
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Popeye Museum

9.4/10 (10 reviews)
Step into the world's only Popeye museum, showcasing rare memorabilia of the iconic sailor and his creator. Explore the Character Trail afterwards to discover whimsical statues throughout Chester.
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Mary's River Covered Bridge

9.0/10 (6 reviews)
This historic 1854 covered bridge, the last of its kind in southern Illinois, showcases original white oak craftsmanship. Photographers capture its timeless charm against seasonal foliage in the peaceful countryside.
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Chester Bridge

This historic 1942 structure spans the Mississippi River, connecting Illinois and Missouri with engineering elegance. Visit the nearby Welcome Centre for panoramic river views and a glimpse of Chester's Popeye heritage.
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Cohen Memorial Home

This 1855 historic residence showcases distinctive blue storm windows and overlooks the Mississippi River. Tour the upstairs bedrooms with authentic furnishings or reserve the parlours for special events by appointment.
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Randolph County State Recreation Area

9.0/10 (2 reviews)
Nestled among 1,101 acres of rolling hills, this recreation area offers serene lakeside activities and wooded trails. Reserve a campsite with electric hookups for the ultimate outdoor retreat surrounded by nature.
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Elzie C. Segar Memorial Park

7.6/10 (4 reviews)
This riverside park honours Elzie Segar, Chester's native son who created the iconic Popeye character. Admire the 900-pound bronze Popeye statue while enjoying scenic Mississippi River views.
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Kaskaskia Bell

10.0/10 (2 reviews)
Cast in 1741 by King Louis XV, the Liberty Bell of the West rang to celebrate America's independence in 1778. Press the button to enter the shrine and view murals depicting Kaskaskia's colonial history.
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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.

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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.