Book Exclusive Chester Vacation Packages

Choose one or more items to build your trip:

Top Chester hotels deals

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street, Chester, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $121 per night
CA $121
CA $134 total
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chester Skating Rink and Popeye Museum are located nearby.
Breakfast included
Pet-friendly
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
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
CA $156 total
includes taxes & fees
28 Apr - 29 Apr
Book a stay at this business-friendly hotel in Festus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Festus Public Library and Lake Ladona are located nearby.
Breakfast included
Pet-friendly
Super 8 by Wyndham Perryville

Super 8 by Wyndham Perryville

2 out of 5
1119 Vincent Dr, Perryville, MO
Free cancellation
Reserve now, pay when you stay
The price is CA $97 per night
CA $97
CA $111 total
includes taxes & fees
14 Apr - 15 Apr
Book a stay at this business-friendly motel in Perryville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Perryville Country Club and Saint Marys Lake are located nearby.
Pool
Breakfast included
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St, Perryville, MO
Free cancellation
The price is CA $147 per night
CA $147
CA $169 total
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Perryville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Perryville Country Club and Saint Marys Lake are located nearby.
Pool
Breakfast included
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
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
CA $122 total
includes taxes & fees
27 Apr - 28 Apr
Book a stay at this business-friendly hotel in Ste Genevieve. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ste Genevieve Museum Learning Center and Ste. Genevieve Historic District are located nearby.
Breakfast included
Pet-friendly
Pinckeyville Inn and Suites

Pinckeyville Inn and Suites

2 out of 5
5700 Illinois Route 154, Pinckneyville, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $125 total
includes taxes & fees
1 Apr - 2 Apr
Book a stay at this business-friendly hotel in Pinckneyville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Pinckneyville Fairgrounds and Pyramid State Recreation Area are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Popular places to visit

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 Vacations

We get it, geography isn't everyone's specialty. If you're not sure where Chester is situated, don't forget to check out its location before you fly off!

The capital of Illinois, Springfield, is located 130 miles (209 kilometers) to the north. Additionally, you'll find Perryville 16 miles (26 kilometers) to the south of Chester.

At the most recent count, the population of this part of Southwest Illinois was 9,000.

Places to visit in Chester

If you've ever wondered how professional figure skaters float so gracefully across the ice, why not give it a crack at Chester Skating Rink? You never know — you might be equally as spellbinding to watch! Need some more options? Bridges are often iconic symbols of a destination. Visit Mary's River Covered Bridge and learn more about how and when it was erected and the important role its played in the city's history. But that's not all there is. If you've got an inquisitive mind, stop at Popeye Museum. You never know what you'll discover here!

Where do you fly into for Chester?

There's nothing quite as exciting as finally arriving in a new, unknown destination. If you're jumping on a plane to Chester, there's every chance you'll step out into MidAmerica-St. Louis Airport (BLV). It's 40 miles (64 kilometers) to the north of the central area. Grab your belongings and get set for a wonderful vacation!

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only . Allow Travelocity to save you money and stress with our excellent vacation packages. With experiences, hotels and flights all ready to go at our one-stop shop, what’s stopping you?
How long should my Chester vacation be?
Generally, people spend 2 nights in Chester. However, that mightn’t be nearly enough time for you. If you’re eager to see some of the area’s off-the-beaten-path treasures, how about adding another few nights to your itinerary?
Where can I get the best vacation package deals for Chester?
It’s hard to look past Travelocity when it comes to crafting your Chester package deal. There are at least 400 partner airlines and 1,000,000 worldwide properties to select from. Lock in your trip now and get ready to tick another exciting destination off your must-see list.
Why should I purchase my Chester vacation bundle via Travelocity?
We make traveling the world easy. Whether you’re looking for an amazing new place to wander around or want to make sure you get the best price on offer, we’ve got your back. Our 24/7 customer support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Will I save money on my Chester car rental if I book it with my hotel or flight?
With a Chester vacation package, you can bundle your hotel, car and flight bookings and save tons. If you want to discover the best of this awesome region, why not head to Busch Stadium? This top attraction is 88 kilometers from Chester. With a rental car, you’ll be there in no time.
Which airport is best for Chester?
There are two options for jetting to Chester, starting with Williamson County Regional Airport (MWA). It’s roughly 72 kilometers from the center of the city, while Cape Girardeau Municipal Airport (CGI) is 80 kilometers away from central Chester.
What is there to do in Chester?
You’ll sense an undeniable magic as you wander the streets of Chester. Popeye Museum and Elzie C. Segar Memorial Park are just two famous attractions that entice visitors to this wonderful city, so put them at the top of your itinerary.
Where should I stay when visiting Chester?
The Best Western Chester Hotel is the first choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Chester vacation photos for more inspiration