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.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $437, price is now $313 per person
$313
per person
Nov 8 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $689, price is now $434 per person
$434
per person
Dec 5 - Dec 7
found 17 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.
White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $902, price is now $677 per person
$677
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Seattle (SEA) to St. Louis (STL)
This apartment features a garden, express check-out, and laundry facilities. The front desk is staffed around-the-clock and barbecue grills are on offer.
Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Price was $519, price is now $405 per person
$405
per person
Dec 12 - Dec 15
found 17 hours ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a grocery/convenience store, and a lobby fireplace are also on offer.
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was $607, price is now $483 per person
$483
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
7 indoor tennis courts, an indoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

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
$72 nightly
The price is $80 total per night
$80 total
Oct 5 - Oct 6
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
$102 nightly
The price is $117 total per night
$117 total
Nov 2 - Nov 3
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
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
$95 nightly
The price is $109 total per night
$109 total
Oct 19 - Oct 20
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
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
$86 nightly
The price is $95 total per night
$95 total
Oct 19 - Oct 20
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 business center and free internet in public areas. A safe deposit box and laundry facilities are also provided.
Breakfast included
Pet friendly
Silo Farm Haus- located in the heart of wine country!

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

$329 nightly
The price is $350 total per night
$350 total
Oct 6 - Oct 7
Total with taxes and fees
This farm stay features a water park and laundry facilities.
Laundry
Holiday Inn Express Hotel & Suites Sparta by IHG

Holiday Inn Express Hotel & Suites Sparta by IHG

2.5 out of 5
1301 N Market St, Sparta, IL
Free Cancellation
$114 nightly
The price is $127 total per night
$127 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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

Mary's River Covered Bridge

4.5/5(2 reviews)

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

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $313. 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