Deals on vacations and trips to Chester

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Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was $477, price is now $397 per person
$397
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like a free area shuttle.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $754, price is now $488 per person
$488
per person
Jan 8 - Jan 11
found 7 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.
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 $662, price is now $520 per person
$520
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $533, price is now $439 per person
$439
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.
Aloft St. Louis Cortex

Aloft St. Louis Cortex

3 out of 5
Central West End
Price was $608, price is now $505 per person
$505
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
This hotel features an indoor pool and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.

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
Dec 25 - Dec 26
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
$91 nightly
The price is $104 total per night
$104 total
Jan 4 - Jan 5, 2026
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
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
Dec 9 - Dec 10
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
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
$87 nightly
The price is $100 total per night
$100 total
Dec 14 - Dec 15
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
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
$63 nightly
The price is $72 total per night
$72 total
Dec 22 - Dec 23
Total with taxes and fees
This motel 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 self-serve breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham Waterloo

Super 8 by Wyndham Waterloo

2 out of 5
112 Warren Dr Waterloo IL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $78 total per night
$78 total
Dec 16 - Dec 17
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
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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

Fort Kaskaskia

5/5(2 reviews)

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

Fort Kaskaskia

Kaskaskia Bell

Find out about the history of Chester with a stop at Kaskaskia Bell. Discover the area's museums and shops.

Kaskaskia Bell

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $397. 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.

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