Chester Vacations from $294

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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.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $382, price is now $294 per person
$294
per person
Dec 12 - Dec 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.2/10 Very Good! (767 reviews)
Just a really nice hotel tucked away from everything, but still close to get whereevre you need to go!

Reviewed on Oct 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $594, price is now $338 per person
$338
per person
Dec 12 - Dec 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,591 reviews)
Fresh and seasonal waffles!

Reviewed on Oct 31, 2025

The Cheshire

The Cheshire

4 out of 5
Price was $526, price is now $395 per person
$395
per person
Dec 12 - Dec 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,008 reviews)
Everything was wonderful. The breakfast was awesome

Reviewed on Nov 1, 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $503, price is now $380 per person
$380
per person
Dec 12 - Dec 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (416 reviews)
A clean and modern hotel right on Wash U grounds. Staff very helpful and rooms well adorned. Breakfast was convenient for morning meetings

Reviewed on Oct 21, 2025

WorldMark Lake of the Ozarks

WorldMark Lake of the Ozarks

3 out of 5
Price was $416, price is now $324 per person
$324
per person
Dec 12 - Dec 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (402 reviews)
Great property! Your balcony view is directly on the water. This property offers a dock unused just for guests. I would bring your own raft or float to enjoy the water. The pools and hot tube area are nice, and offer grills for cooking in the pool area and another location. Check in was great except our room wasn’t ready until 5, the check in time was 4, however they made accommodations to us to offset the delay. It’s close to many fun things to do at the Lake of the Ozarks!! We will be back and will stay here again.

Reviewed on Aug 10, 2025

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Discover the most popular places to visit in Chester

Popeye Museum

4.5/5(3 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.

Popeye Museum

Fort Kaskaskia

5/5(2 reviews)

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

Fort Kaskaskia

Mary's River Covered Bridge

4.5/5(2 reviews)

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
$75 nightly
The price is $83 total per night from Nov 9 to Nov 10
$83 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (341 reviews)
The room was clean and the staff were friendly.

Reviewed on Oct 20, 2025

Baymont by Wyndham Chester IL
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
$81 nightly
The price is $93 total per night from Nov 4 to Nov 5
$93 total
Nov 4 - Nov 5
Total with taxes and fees
6.8/10 (904 reviews)
I really don't want to give them a lousy review because they are trying to do repairs on the building. Beds were comfy, breakfast was good, tv works, and a nice shower!

Reviewed on Oct 13, 2025

Baymont by Wyndham Festus
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 9 to Nov 10
$112 total
Nov 9 - Nov 10
Total with taxes and fees
7.8/10 Good! (870 reviews)
Our biggest concern was the sheets had dried blood stains on them. We told the clerk when we checked out

Reviewed on Oct 24, 2025

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
See all 151 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.

Find the Best Chester Vacation Packages

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 $294 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.