Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Rolla

Super 8 by Wyndham Rolla

2 out of 5
per person
Aug. 5 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
No real area for pets. Trash completely full outside & no good area to walk a dog. Smelled bad on first floor hallway.

Reviewed on May 31, 2024

Baymont by Wyndham Rolla

Baymont by Wyndham Rolla

2.5 out of 5
per person
Aug. 5 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8/10 Very Good! (1,001 reviews)
For being next to the interstate, it was surprisingly quiet

Reviewed on May 31, 2024

Super 8 by Wyndham Cuba

Super 8 by Wyndham Cuba

2 out of 5
per person
Aug. 5 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.8/10 Excellent! (807 reviews)
Not in the middle of a busy place and it was easy to find right off the highway.

Reviewed on May 31, 2024

Days Inn & Suites by Wyndham Cuba

Days Inn & Suites by Wyndham Cuba

2 out of 5
per person
Aug. 5 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
7.2/10 Good! (577 reviews)
Hotel is listed as a "suite" hotel, it is not. Doesnt have all the furniture for a suite. 1st room we checked into only had a table and no chairs, second room had a table and chair but the furniture was old and not up to date. Tv was ok, remote didnt coinside with the tv cable company and closed caption could not be turned off. Carpet in rooms were old and not cleaned. Beds were worn and mattresses needed to be turned or replaced. Breakfast was surely poor. Only cereals or waffles. Coffee was poor. Too many potted plants that needed help....lobby furniture was old and needed repair. Pool was cloudy, needed some heat. Tile in pool area was loose and unsafe. Outside garbage cans needed to be emptied. We stayed here for a family function because it was close. May not stay again.

Reviewed on May 20, 2024

Days Inn by Wyndham Rolla

Days Inn by Wyndham Rolla

2.5 out of 5
per person
Aug. 5 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Interstate traffic loud- but that can’t b helped

Reviewed on May 25, 2024

Chester Hotel Deals

Best Western Chester Hotel
Best Western Chester Hotel
2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Jun. 5 to Jun. 6
CA $119
CA $132 total
includes taxes & fees
Jun 5 - Jun 6
8.6/10 Excellent! (252 reviews)
"Quiet, good service,good breakfast"

Reviewed on May 28, 2024

Best Western Chester Hotel
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jun. 18 to Jun. 19
CA $127
CA $146 total
includes taxes & fees
Jun 18 - Jun 19
7.8/10 Good! (613 reviews)
"The rooms are clean. The communal are is under some renovation, but the breakfast is excellent. The public areas aren't as neat as I normally like, though. Good thing the rooms are clean and neat, though."

Reviewed on May 28, 2024

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Super 8 by Wyndham Perryville
Super 8 by Wyndham Perryville
2 out of 5
1119 Vincent Dr, Perryville, MO
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Jun. 9 to Jun. 10
CA $87
CA $99 total
includes taxes & fees
Jun 9 - Jun 10
8.4/10 Very Good! (742 reviews)
"Great staff across the board!"

Reviewed on May 28, 2024

Super 8 by Wyndham Perryville
See all 157 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.

All Inclusive Vacations

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Frequently asked questions

How much does a Chester vacation package cost?
Our Chester vacation packages, which begin from just CA $860, are the best way to save big. Select your preferred flights, hotels and rental cars to create your dream escape.
How do I get a cheap travel package to Chester?
Crafting your own Chester vacation package with Expedia is a simple way to save. We have access to more than 550 air carriers and 1,000,000 hotel options across the globe. With such a fabulous range to select from, you’ll have no hassles pulling together your perfect vacation.
Where should I stay in Chester?
A trip to Chester isn’t complete without paying a visit to Chester Skating Rink, Popeye Museum and Memorial Hospital. Spend your evenings close to these attractions and make sightseeing simple.
What are the top hotels in Chester?
When it comes to comfortable and convenient places to stay in Chester, you can’t go past Best Western Chester Hotel. Have a look at its deals and score a great price.
How far in advance should I book my Chester vacation?
Savvy travelers will likely want to reserve their seats early. You can usually start comparing international airfares on Expedia up to a year before your intended flight. If you’ve left booking to the last minute, fear not. Discounted prices occasionally occur in the last weeks before departure dates.
What does an Expedia Chester travel package include?
Hotels, rental cars and flights, or any combination of them — it’s your choice. Whether you’re headed to Chester with the kids or adventuring with your friends, there’s a package to suit every budget and style. Once you’ve made your booking, why not add on a few tours as well?
What should I know before booking a Chester travel package?
You’ll score great savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning easier. So why waste time or money? Whether you’re organizing a luxury city stay with your love or a low-cost family road trip, check out our vacation packages today.
Can I choose my airline with a Chester Expedia vacation package?
Yes, you’re in charge. We offer more than 550 partner airlines all over the world, so you can customize your Chester adventure according to your budget and needs.
If I'm not able to travel, can I cancel my Chester vacation package?
It is possible to cancel your Chester booking if your plans have been upended. Whether you’ll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Chester

Image for Popeye Museum

Popeye Museum

Rich with history, Popeye Museum is a cultural attraction worth visiting in Chester. Amble around the area's parks or visit its shops.

Popeye Museum
Image for Fort Kaskaskia

Fort Kaskaskia

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

Fort Kaskaskia
Image for Kaskaskia Bell

Kaskaskia Bell

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

Kaskaskia Bell

Other vacations you might like

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