Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $890, price is now $576 per person
$576
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
New York (LGA) 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 $785, price is now $631 per person
$631
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Price was $688, price is now $593 per person
$593
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
New York (LGA) 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, free WiFi in public areas, and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and concierge services.
The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
Price was $676, price is now $584 per person
$584
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was $758, price is now $661 per person
$661
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
New York (LGA) 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
$80 nightly
The price is $89 total per night
$89 total
Nov 8 - Nov 9
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
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
$141 nightly
The price is $160 total per night
$160 total
Nov 11 - Nov 12
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
Days Inn by Wyndham Perryville

Days Inn by Wyndham Perryville

2 out of 5
1500 Liberty Street Perryville MO
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $77 total per night
$77 total
Oct 14 - Oct 15
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a seasonal outdoor pool on site, and laundry facilities and free newspapers are also offered.
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
$101 nightly
The price is $116 total per night
$116 total
Nov 1 - Nov 2
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
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
Nov 1 - Nov 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet 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 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
$100 nightly
The price is $111 total per night
$111 total
Nov 1 - Nov 2
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
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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.

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.
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Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $576. 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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