Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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Alhonna Resort LLC

Alhonna Resort LLC

3 out of 5
Price was $513, price is now $370 per person
$370
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to St. Louis (STL)
This resort features a private beach, a marina, and a restaurant. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.
Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Save 100% on your flight
Price was $1,220, price is now $741 per person
$741
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to St. Louis (STL)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $573, price is now $386 per person
$386
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
Price was $600, price is now $454 per person
$454
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was $614, price is now $478 per person
$478
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to St. Louis (STL)
The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the a restaurant 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
$82 nightly
The price is $91 total per night
$91 total
Jul 1 - Jul 2
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.
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
$84 nightly
The price is $96 total per night
$96 total
Jun 30 - Jul 1
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 $143 total per night
$143 total
Jul 27 - Jul 28
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
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
$106 nightly
The price is $121 total per night
$121 total
Jul 27 - Jul 28
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.
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
$92 nightly
The price is $108 total per night
$108 total
Jul 12 - Jul 13
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
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
$64 nightly
The price is $73 total per night
$73 total
Jul 26 - Jul 27
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
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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

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

Fort Kaskaskia

5/5(2 reviews)

Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia.

Fort Kaskaskia

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $370. 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.

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