Chester Vacations from $261

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Your Chester Vacation

With a Chester vacation 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 vacation to Chester to suit your travel style, whatever that may look like.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was $346, price is now $261 per person
$261
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,006 reviews)
Alex who checked us in was awesome, super efficient, professional and helpful. Gold star!

Reviewed on Oct 10, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $871, price is now $575 per person
$575
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
Has a parking garage or street parking patrolled by local police constantly. We did not try the hotel breakfast we went to “The Pancake House” for breakfast and it was awesome.

Reviewed on Oct 12, 2025

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $432, price is now $305 per person
$305
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
Awesome hotel with awesome/helpful staff! The area around is mostly safe, nighttime can get a lil scary but the hotel itself is really safe.

Reviewed on Oct 11, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $406, price is now $287 per person
$287
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (62 reviews)
One night stay to catch a flight Easy check in, room was clean and ready for us Shuttle to airport was right on schedule Excellent experience

Reviewed on Oct 13, 2025

DoubleTree by Hilton St. Louis - Westport

DoubleTree by Hilton St. Louis - Westport

4 out of 5
Price was $397, price is now $300 per person
$300
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,004 reviews)
The property was very nice however, my main kudos goes to the staff. There was a plumbing issue. They got me to another room and will refund a one night‘s stay

Reviewed on Sep 29, 2025

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Discover the most popular places to visit in Chester

Popeye Museum

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.

Popeye Museum

Fort Kaskaskia

Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia.

Fort Kaskaskia

Mary's River Covered Bridge

Learn about the local history of Chester when you take a trip to Mary's River Covered Bridge. Amble around the area's parks or visit its shops.

Mary's River Covered Bridge

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
$74 nightly
The price is $82 total per night from Oct 26 to Oct 27
$82 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (336 reviews)
"Great staff, clean rooms"

Reviewed on Sep 8, 2025

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
$98 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (861 reviews)
"The first night was in a room that desperately needed renovation. They moved us the second night and the room was very good."

Reviewed on Oct 2, 2025

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
$103 nightly
The price is $118 total per night from Oct 20 to Oct 21
$118 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (516 reviews)
"Rooms were clean and everyone was really nice. Only thing I would say is that for the breakfast, the bacon wasn't quite all the way done other than that, a good experience."

Reviewed on Oct 7, 2025

Holiday Inn Express & Suites Perryville by IHG
See all 149 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.

Chester Essential Information

Language
English
Currency
U.S dollars
Population
8,600
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Randolph County State Recreation Area, Chester Skating Rink and Marys River Covered Bridge

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Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from $261 on Expedia. But how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
You're likely to find reduced prices and greater availability in February, August and September. Take a look at our cheap Chester vacation packages and you could get some great off-season discounts.
How many days is enough for Chester?
The ideal length for your Chester vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the main attractions and discover some hidden spots along the way.
Is it worth booking a vacation package to Chester?
It's no wonder a Chester vacation is on the to-do list of many travelers. Top attractions like Chester Skating Rink are just the start of things to see and do here.
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 vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester break is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.