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 ₩136,068 per night from May 7 to May 8
₩136,068
₩151,009 total
includes taxes & fees
May 7 - May 8
8.6/10 Excellent! (295 reviews)
"I stay here usually once a month. Its a nice place the staff is very friendly and the price is decent"

Reviewed on Apr 17, 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 ₩164,355 per night from May 11 to May 12
₩164,355
₩187,940 total
includes taxes & fees
May 11 - May 12
7.8/10 Good! (777 reviews)
A Quick Stay!!
"The staff was very helpful & kind...it was a quick check-in process, had one minor incident but it wouldn't deter me from staying with the property again."

Reviewed on Apr 21, 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
The price is ₩147,526 per night from May 4 to May 5
₩147,526
₩168,880 total
includes taxes & fees
May 4 - May 5
9.2/10 Wonderful! (456 reviews)
Sleep saver <3
"I was flooded out of going home after vacation. I was able to stay at the HIE through Hotels.com. The staff had me ready to go when I got there. They have amazing electric blinds to block the sunlight...I work nights."

Reviewed on Apr 10, 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.

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 many days is enough for Chester?
With a well-organized itinerary, you can easily tick off the most popular Chester attractions in a few days. But if you’d like to discover hidden gems or go on day trips, consider booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Elzie C. Segar Memorial Park among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
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

Chester Skating Rink

4/5(1 review)

Enjoy an outing to Chester Skating Rink during your stay in Chester. Discover the area's museums and shops.

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