Chester, IL

Travel Guide

A steel bridge over a river with a white boat.
A large, single-story house with a covered porch and a staircase leading to the entrance.
Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street Chester IL
$81 nightly
The price is $90 total per night from Nov 8 to Nov 9
$90 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (425 reviews)
"Breakfast area was poorly stocked. Coffee machine broken. Juice machine off most days. Bread products stale. Waffle mix was clearly not fresh. In the room there were missing knows and empty soap and shampoo dispensers. Clearly a decent place that needs a step up to be good or great. Lobby area was ..."

Reviewed on Oct 5, 2026

Baymont by Wyndham Chester IL
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

2 out of 5
7555 State Hwy Y French Village MO
$141 nightly
The price is $160 total per night from Nov 8 to Nov 9
$160 total
Nov 8 - Nov 9
Total with taxes and fees
Stay at this cabin in French Village. Enjoy free parking, patios, and climate control.
10/10 Exceptional! (112 reviews)
"Peaceful getaway. Pet friendly. Safe area"

Reviewed on Oct 7, 2026

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Days Inn by Wyndham Perryville

Days Inn by Wyndham Perryville

2 out of 5
1500 Liberty Street Perryville MO
$68 nightly
The price is $77 total per night from Oct 11 to Oct 12
$77 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Perryville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perryville Country Club and ...
7/10 Good! (458 reviews)
"When renting a motel room under 100 bucks you have to remember, you’re not at the Hilton. This is an aging building although it has been kept up, the bed was comfortable. I slept well. The shower was fantastic and plenty of hot water super easy access and parking . The continental breakfast was better ..."

Reviewed on Sep 28, 2026

Days Inn by Wyndham Perryville
See all 166 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.
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

2 out of 5
7555 State Hwy Y French Village MO
Stay at this cabin in French Village. Enjoy free parking, patios, and climate control.
10/10 Exceptional! (112 reviews)
"Peaceful getaway. Pet friendly. Safe area"

Reviewed on Oct 7, 2026

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Silo Farm Haus- located in the heart of wine country!

Silo Farm Haus- located in the heart of wine country!

Ste. Genevieve MO
Stay at this vacation home in Ste Genevieve. Enjoy laundry facilities. Popular attractions Crown Valley Winery and Hawn State Park are located nearby.
10/10 Exceptional! (158 reviews)
"This place is absolutely gorgeous! We really enjoyed our stay. The silo farm haus was serene, clean and comfortable. Thank you for a wonderful stay!"

Reviewed on Sep 19, 2026

Silo Farm Haus- located in the heart of wine country!
Private Cabin with Pond on Family Farm

Private Cabin with Pond on Family Farm

Belleville IL
Stay at this cabin in St. Clair County. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
Private Cabin with Pond on Family Farm
See all 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

Popeye Museum

9.4/10 (10 reviews)
You can browse the exhibits at Popeye Museum, a museum with a story of its own, during your travels to Chester. Discover the area's museums and shops.
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Frequently asked questions

Is Chester worth visiting?
Chester is worth visiting for its standout attractions, including Fort Kaskaskia and Elzie C. Segar Memorial Park. Travelers can also enjoy a variety of food and local dining options, with cuisine types ranging from Italian to North American dishes.
When is the best time to visit Chester?
The best time to visit Chester is from May through September, when travelers can enjoy generally mild and pleasant weather. For fewer crowds and better value, the cooler months of November through February are a good option, offering a different experience with a quieter atmosphere.
What is Chester known for?
Chester is known for historical sites like Fort Kaskaskia, along with attractions such as Elzie C. Segar Memorial Park and the Popeye Museum. Travelers can also find Italian food culture in this riverside city, located along the Mississippi River.
What is a good itinerary length for Chester?
A good itinerary length for Chester is one to two days to explore key attractions like Fort Kaskaskia, Elzie C. Segar Memorial Park, and the Popeye Museum. An extended stay of three to four days allows travelers to enjoy these sites at a more relaxed pace and experience the local area more deeply.
What are the top things to do in and around Chester?
Chester offers a blend of historical sites, natural spaces, and unique local interests:


How do I plan a trip to Chester?
To plan your trip to Chester, search for places to stay on Expedia and book flights in advance. Explore attractions like Fort Kaskaskia, Elzie C. Segar Memorial Park, and the Popeye Museum. When planning outdoor activities, always have indoor backups ready for weather flexibility. A rental car can help you explore the area.
What cuisines can you find in Chester?
In Chester you can find Mexican cuisine, with popular dishes like tacos, burritos, and enchiladas. Travelers can also enjoy Italian, North American options such as Southern soul food and New American dishes, as well as Asian choices like Chinese, Japanese, and Thai. Mediterranean and other Latin American flavors are also available.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chester

A town with a mix of residential houses, a church, and a golf course.

Sparta

A train crossing a stone bridge over a river, surrounded by lush greenery.

Perryville

Other places like Chester

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