Chester Vacations

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Find the Best Chester Vacation Packages

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
The price is AED 342 per night from May 4 to May 5
AED 342
AED 380 total
includes taxes & fees
4 May - 5 May
8.6/10 Excellent! (294 reviews)
Great place
"Great place at a great price. Friendly service"

Reviewed on 11 April 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
2.5 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is AED 387 per night from Apr 28 to Apr 29
AED 387
AED 443 total
includes taxes & fees
28 Apr - 29 Apr
7.8/10 Good! (774 reviews)
"Room was decent. Could tell the hotel is older. Caulking in bathroom was horrible, lights in restroom flickering. Room and sheets were clean, bedframe creaked badly. Hallways smelled musty. For just a place to sleep and explore the area it did the job"

Reviewed on 13 April 2025

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 AED 259 per night from May 4 to May 5
AED 259
AED 297 total
includes taxes & fees
4 May - 5 May
8.4/10 Very Good! (845 reviews)
"The staff was very friendly and the guy at the front desk was helpful with ever thing we asked about hotel was nice clean and quiet. Thus was my second time staying at this same hotel"

Reviewed on 30 March 2025

Super 8 by Wyndham Perryville
See all 140 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.

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination 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?
If you’d like to score a cheap Chester vacation package, consider visiting in December, January and February. You’ll usually find lower rates on flights and accommodations during these months — ideal for travelers wishing to save money.
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.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to Chester.
  3. Decide how long to go away for: Now that you’re more familiar with Chester, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Chester vacation package.

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