Chester Vacations from $246

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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.
Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West

Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West

3 out of 5
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.2/10 Good! (1,015 reviews)
The location was close to the airport. The area was quiet. My only issue was that my swim shorts were stolen at the pool. I left it there to dry out under the sun. Other than that, everything else seemed to be good.

Reviewed on Jun 28, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
Save 100% on your flight
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.2/10 Good! (7 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun 8, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Quirky property with an old English theme. A bit of a haunted house vibe. Checking in was an annoyance as we arrived at 11:45pm and the lone staff that could check us in had a car mishap on her way to work and we had to sit and wait in the lobby for more than an hour and only was able to get into the room at 1am. The staff did apologize and I understood it was out of her control but it was still annoying. The rooms were fairly clean. The staff was polite but not overly friendly.

Reviewed on Jun 26, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
Room had issues. Addressed with staff.

Reviewed on Jun 25, 2025

Home2 Suites by Hilton St. Louis/Forest Park

Home2 Suites by Hilton St. Louis/Forest Park

3 out of 5
The Grove
per person
Aug 13 - Aug 16
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
8.8/10 Excellent! (1,000 reviews)
Everything was great! Staff was super friendly. The rooms were really nice and big. The bathrooms could have been a bit more cleaner but it was good.

Reviewed on Jun 13, 2025

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Discover the most popular places to visit in Chester

Fort Kaskaskia

5/5(2 reviews)

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

Fort Kaskaskia

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

Elzie C. Segar Memorial Park

4/5(3 reviews)

Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops.

Elzie C. Segar Memorial Park

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
$89 nightly
The price is $99 total per night from Jul 1 to Jul 2
$99 total
Jul 1 - Jul 2
Total includes taxes and fees
8.6/10 Excellent! (310 reviews)
"Monic"

Reviewed on Jun 27, 2025

Baymont by Wyndham Chester IL
Microtel Inn & Suites by Wyndham Sainte Genevieve
Microtel Inn & Suites by Wyndham Sainte Genevieve
2.5 out of 5
21958 Hwy 32, Ste Genevieve, MO
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Jul 6 to Jul 7
$85 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (577 reviews)
Gross cleaning service in front of guests at bkfst
"The first morning we ate breakfast (24th) as we were in the breakfast room I witnessed a female cleaning the area. She used a rag to scrub at the floor in front of the coffee machine. Nothing unusual, but I kept watching. She then stood up, rinsed out the rag then immediately started to wipe down ..."

Reviewed on Jun 27, 2025

Microtel Inn & Suites by Wyndham Sainte Genevieve
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
$94 nightly
The price is $108 total per night from Jul 13 to Jul 14
$108 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (474 reviews)
"Was clean. Pool was nice. Breakfast was good"

Reviewed on Jun 12, 2025

Holiday Inn Express & Suites Perryville by IHG
See all 142 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 $246 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.