Deals on vacations and trips to Chester

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The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $589, price is now $413 per person
$413
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was $620, price is now $521 per person
$521
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and 24-hour gym, and unwind with a drink at the poolside bar.
Landing Apartments - Eureka

Landing Apartments - Eureka

4 out of 5
Price was $705, price is now $597 per person
$597
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
This aparthotel features an outdoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A virtual front desk are provided for your convenience.
Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was $720, price is now $612 per person
$612
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to St. Louis (STL)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking. Self parking, dry cleaning, and luggage storage are also offered.
The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $506, price is now $432 per person
$432
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

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
$79 nightly
The price is $88 total per night
$88 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. 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
$93 nightly
The price is $106 total per night
$106 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
Jan 1 - Jan 2, 2026
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
$91 nightly
The price is $104 total per night
$104 total
Jan 1 - Jan 2, 2026
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
Silo Farm Haus- located in the heart of wine country!

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

Ste. Genevieve MO
$329 nightly
The price is $350 total per night
$350 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
This farm stay features a water park and laundry facilities.
Laundry
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
$66 nightly
The price is $76 total per night
$76 total
Jan 11 - Jan 12, 2026
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
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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

Randolph County State Recreation Area

You can take time to visit Randolph County State Recreation Area during your travels to Chester. Amble around the area's parks or experience its entertainment venues.

Randolph County State Recreation Area

Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $413. 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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