Chester Vacations from $306

Book a Hotel + Flight or Car together to unlock savings

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 Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
per person
Oct 24 - Oct 26
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.

Reviewed on Jul 27, 2025

WorldMark Lake of the Ozarks

WorldMark Lake of the Ozarks

3 out of 5
per person
Oct 31 - Nov 4
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
9.4/10 Exceptional! (400 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

Courtyard by Marriott St. Louis Downtown/Convention Center

Courtyard by Marriott St. Louis Downtown/Convention Center

3 out of 5
Downtown St. Louis
per person
Oct 24 - Oct 26
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9/10 Wonderful! (1,004 reviews)
Valet greeted you at the door check in was quick and easy rooms were spacious and very clean

Reviewed on Aug 10, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Oct 24 - Oct 26
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
It was nice but the room could use some updates and the bathroom set up was not good, had a glass panel on the door , so couldn't leave light on at night. The beds were ok but more like doubles than queens. Kind of felt like I was staying at an older persons house.The breakfast wasn't that great., had quite a few pastries but eggs were cold.The pool was nice and the staff was freindly.Wallpaper was peeling in bathroom and some outlets didn't work.

Reviewed on Aug 16, 2025

Days Inn by Wyndham Osage Beach Lake of the Ozarks

Days Inn by Wyndham Osage Beach Lake of the Ozarks

2 out of 5
per person
Oct 31 - Nov 4
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
7.2/10 Good! (1,000 reviews)
Beds were super comfy, good breakfast, eggs were a little hard. Great location. Would stay here again.

Reviewed on Aug 15, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

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
$75 nightly
The price is $83 total per night from Sep 7 to Sep 8
$83 total
Sep 7 - Sep 8
Total includes taxes and fees
8.4/10 Very Good! (328 reviews)
"just a nice clean place to stay, not very far from shooting complex at Sparta"

Reviewed on Aug 4, 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
$111 nightly
The price is $127 total per night from Aug 27 to Aug 28
$127 total
Aug 27 - Aug 28
Total includes taxes and fees
7.8/10 Good! (828 reviews)
"Truly amazed by the speed of check-in. The clerk on duty had her paperwork all ready, spread out on a desk. She seemed to guess which guest I was and just handed over the document to initial. Perfect efficiency! Also, she was pleasant. The lobby, stairs and hallways had been recently upgraded. Room ..."

Reviewed on Jul 21, 2025

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Postcard Cabins St. Francois

Postcard Cabins St. Francois

2 out of 5
7555 State Hwy Y, French Village, MO
$124 nightly
The price is $133 total per night from Aug 17 to Aug 18
$133 total
Aug 17 - Aug 18
Total includes taxes and fees
9.8/10 Exceptional! (25 reviews)
"Sweet cabin"

Reviewed on Aug 12, 2025

Postcard Cabins St. Francois
See all 145 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from $306 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.