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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $629, price is now $344 per person
$344
per person
Oct 20 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $627, price is now $446 per person
$446
per person
Oct 20 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $569, price is now $442 per person
$442
per person
Oct 20 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. Self parking, express check-out, and a computer station are also offered.
WorldMark Lake of the Ozarks

WorldMark Lake of the Ozarks

3 out of 5
Price was $759, price is now $594 per person
$594
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to St. Louis (STL)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-in, express check-out, and a computer station are also on offer.
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Save 100% on your flight
Price was $641, price is now $512 per person
$512
per person
Oct 20 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and outdoor pool, and unwind with a drink at the poolside bar.

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
$73 nightly
The price is $81 total per night
$81 total
Aug 30 - Aug 31
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
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
$67 nightly
The price is $76 total per night
$76 total
Sep 20 - Sep 21
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.
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
$101 nightly
The price is $116 total per night
$116 total
Aug 30 - Aug 31
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
$133 nightly
The price is $151 total per night
$151 total
Sep 1 - Sep 2
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
Silo Farm Haus- located in the heart of wine country!

Silo Farm Haus- located in the heart of wine country!

Ste. Genevieve MO
$331 nightly
The price is $370 total per night
$370 total
Aug 29 - Aug 30
Total with taxes and fees
This vacation home features laundry facilities.
Laundry
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
$97 nightly
The price is $111 total per night
$111 total
Sep 3 - Sep 4
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.

Stay near popular Chester attractions

Popeye Museum

9.4/10 (10 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.
See properties

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $344. 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

A steel bridge over a river with a white boat.
A large, single-story house with a covered porch and a staircase leading to the entrance.

Explore More Ways to Travel with Travelocity