Chester Vacations from $487

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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.
 White House at Grand Central
The Wildwood Hotel
Hilton Garden Inn Chesterfield
HoteLumiere at the Arch
River City Casino & Hotel

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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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 $102 per night from May 11 to May 12
$102
includes taxes & fees
$92 per night
May 11 - May 12
8.6/10 Excellent! (296 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 $129 per night from May 25 to May 26
$129
includes taxes & fees
$113 per night
May 25 - May 26
7.8/10 Good! (780 reviews)
"Large shopping area and ease of travel."

Reviewed on Apr 25, 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 $118 per night from May 4 to May 5
$118
includes taxes & fees
$103 per night
May 4 - May 5
9.2/10 Wonderful! (458 reviews)
"Great place to stay!"

Reviewed on Apr 25, 2025

Holiday Inn Express & Suites Perryville by IHG
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 from $487 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.

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