Chester Vacations from $358

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $693, price is now $358 per person
$358
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
18.4/10 Exceptional! (1,600 reviews)
Everything was good except the hot tub was down.

Reviewed on Nov 25, 2025

HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $646, price is now $374 per person
$374
per person
Jan 7 - Jan 11
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
13.2/10 Exceptional! (1,001 reviews)
It was very nice resort

Reviewed on Nov 20, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $649, price is now $418 per person
$418
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,002 reviews)
Great stay! The room could have been a tiny bit cleaner but nothing crazy! Mainly stains on the table and some dusty areas but beds and bathrooms were clean! The staff was super nice and the place was nicely decorated.

Reviewed on Nov 15, 2025

Home2 Suites by Hilton St. Louis/Forest Park

Home2 Suites by Hilton St. Louis/Forest Park

3 out of 5
The Grove
Save 100% on your flight
Price was $737, price is now $483 per person
$483
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,000 reviews)
Everything was perfect A bit more attention to detail is needed. A deep clean on a regular basis.

Reviewed on Nov 10, 2025

Marriott St. Louis West

Marriott St. Louis West

3.5 out of 5
Save 100% on your flight
Price was $574, price is now $377 per person
$377
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,000 reviews)
Parking area felt very safe

Reviewed on Oct 14, 2025

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

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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

Kaskaskia Bell

Find out about the history of Chester with a stop at Kaskaskia Bell. Discover the area's museums and shops.

Kaskaskia Bell

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
$68 nightly
The price is $75 total per night from Dec 19 to Dec 20
$75 total
Dec 19 - Dec 20
Total with taxes and fees
8.4/10 Very Good! (345 reviews)
Bed was ok. Staff was nice

Reviewed on Nov 9, 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 30 to Dec 1
$112 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (880 reviews)
The staff was amazing!!

Reviewed on Nov 22, 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
$87 nightly
The price is $100 total per night from Nov 30 to Dec 1
$100 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (532 reviews)
Tv is slanted on the wall

Reviewed on Nov 22, 2025

Holiday Inn Express & Suites Perryville by IHG
See all 155 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

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 $358 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.