Chester Vacations from $247

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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.
Super 8 by Wyndham St Charles

Super 8 by Wyndham St Charles

2 out of 5
per person
Oct 17 - Oct 20
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to St. Louis (STL)
8/10 Very Good! (1,003 reviews)
Great breakfast and awesome staff

Reviewed on Jul 31, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.8/10 Exceptional! (88 reviews)
Very clean quiet , room excellent ,mattress very comfortable, extra towels Overall experience awesome.

Reviewed on Jul 26, 2025

La Quinta Inn & Suites by Wyndham St Louis Route 66

La Quinta Inn & Suites by Wyndham St Louis Route 66

3 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.8/10 Good! (1,012 reviews)
Check in staff was very friendly and helpful. And quick to check us in.

Reviewed on Jul 30, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
Sep 5 - Sep 7
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to St. Louis (STL)
7.4/10 Good! (9 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

Comfort Suites Rolla

Comfort Suites Rolla

2.5 out of 5
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
8.8/10 Excellent! (857 reviews)
Room was clean and everything was in great condition

Reviewed on Aug 1, 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
$86 nightly
The price is $96 total per night from Aug 14 to Aug 15
$96 total
Aug 14 - Aug 15
Total includes taxes and fees
8.6/10 Excellent! (323 reviews)
"Was a nice hotel. Covered everything that we needed for our stay."

Reviewed on Jul 29, 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
$109 nightly
The price is $124 total per night from Aug 31 to Sep 1
$124 total
Aug 31 - Sep 1
Total includes taxes and fees
7.8/10 Good! (825 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
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
$90 nightly
The price is $101 total per night from Aug 14 to Aug 15
$101 total
Aug 14 - Aug 15
Total includes taxes and fees
8.6/10 Excellent! (583 reviews)
"It was a great stay. Only thimg maybe more variety or hot breakfast."

Reviewed on Jul 21, 2025

Microtel Inn & Suites by Wyndham Sainte Genevieve
See all 146 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.

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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 $247 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.