Deals on vacations and trips to Chester

Save when you book Chester package deals

Choose two or more items and save on your trip:

Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
Price was $423, price is now $321 per person
$321
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
This hotel features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a garden, and express check-out are also on offer.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $560, price is now $344 per person
$344
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $532, price is now $392 per person
$392
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
This apartment features a garden, express check-out, and laundry facilities. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. The front desk is staffed around-the-clock and barbecue grills are on offer.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $523, price is now $394 per person
$394
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 6 conference rooms, along with free WiFi in public areas. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.
The Cheshire

The Cheshire

4 out of 5
Price was $580, price is now $441 per person
$441
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free English breakfast each morning.

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
$70 nightly
The price is $78 total per night
$78 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
1001 Veterans Blvd Festus MO
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $110 total per night
$110 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a convenience store are also provided.
Breakfast included
Pet friendly
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

2 out of 5
7555 State Hwy Y French Village MO
$134 nightly
The price is $144 total per night
$144 total
Feb 5 - Feb 6
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Baymont by Wyndham Festus

Baymont by Wyndham Festus

3 out of 5
1200 W. Gannon Drive Festus MO
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $93 total per night
$93 total
Feb 5 - Feb 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.
Pool
Breakfast included
Days Inn by Wyndham Perryville

Days Inn by Wyndham Perryville

2 out of 5
1500 Liberty Street Perryville MO
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $84 total per night
$84 total
Feb 5 - Feb 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a seasonal outdoor pool on site, and laundry facilities and free newspapers are also offered.
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
$91 nightly
The price is $104 total per night
$104 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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

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

Elzie C. Segar Memorial Park

4/5(3 reviews)

Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops.

Elzie C. Segar Memorial Park

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $321. 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 55 mi 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 45 mi from the center of the city, while Cape Girardeau Municipal Airport (CGI) is 50 mi 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

View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.
View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.
Pierre Menard Home

Explore More Ways to Travel with Travelocity