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Chester

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Chester Flights as Low as $99

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

United
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$99 Roundtrip, found 10 hours ago
$99
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $99 found 10 hours ago
United
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$99 Roundtrip, found 10 hours ago
$99
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $99 found 10 hours ago
Frontier Airlines
Sat, Oct 4 - Sat, Oct 11
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 4 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Oct 11, priced at $100 just found
American Airlines
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$106 Roundtrip, found 10 hours ago
$106
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $106 found 10 hours ago
American Airlines
Tue, Sep 9 - Mon, Sep 15
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$106 Roundtrip, found 10 hours ago
$106
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Sep 15, priced at $106 found 10 hours ago
Frontier Airlines
Thu, Aug 28 - Thu, Sep 4
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Dallas-Fort Worth Intl. to Lambert-St. Louis Intl., returning Thu, Sep 4, priced at $126 found 2 days ago
Frontier Airlines
Fri, Oct 3 - Mon, Oct 6
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 3 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Mon, Oct 6, priced at $163 found 1 day ago
Delta
Thu, Sep 11 - Fri, Sep 12
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 11 from O'Hare Intl. to Lambert-St. Louis Intl., returning Fri, Sep 12, priced at $177 found 1 day ago
American Airlines
Wed, Sep 10 - Tue, Sep 16
OKC
Will Rogers World
STL
Lambert-St. Louis Intl.
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 10 from Will Rogers World to Lambert-St. Louis Intl., returning Tue, Sep 16, priced at $178 found 5 days ago
Southern Airways Express
Thu, Sep 11 - Thu, Sep 18
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Southern Airways Express flight, departing Thu, Sep 11 from O'Hare Intl. to Lambert-St. Louis Intl., returning Thu, Sep 18, priced at $185 found 1 day ago
Bargain Flight
Tue, Sep 30 - Fri, Oct 3
IND
Indianapolis Intl.
STL
Lambert-St. Louis Intl.
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Sep 30 from Indianapolis Intl. to Lambert-St. Louis Intl., returning Fri, Oct 3, priced at $212 found 1 day ago
Spirit Airlines
Sun, Aug 31 - Mon, Sep 1
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$213 Roundtrip, found 6 days ago
$213
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sun, Aug 31 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Mon, Sep 1, priced at $213 found 6 days ago
American Airlines
Wed, Sep 10 - Sun, Sep 21
FSD
Sioux Falls Regional
STL
Lambert-St. Louis Intl.
$233 Roundtrip, found 14 hours ago
$233
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Sep 10 from Sioux Falls Regional to Lambert-St. Louis Intl., returning Sun, Sep 21, priced at $233 found 14 hours ago
Delta
Thu, Aug 28 - Thu, Sep 4
DAL
Love Field
STL
Lambert-St. Louis Intl.
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 28 from Love Field to Lambert-St. Louis Intl., returning Thu, Sep 4, priced at $301 found 2 days ago
American Airlines
Fri, Sep 19 - Mon, Sep 22
FLO
Florence Regional
STL
Lambert-St. Louis Intl.
$391 Roundtrip, found 1 day ago
$391
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 19 from Florence Regional to Lambert-St. Louis Intl., returning Mon, Sep 22, priced at $391 found 1 day ago
American Airlines
Wed, Aug 20 - Sat, Aug 23
DSM
Des Moines Intl.
STL
Lambert-St. Louis Intl.
$484 Roundtrip, found 17 hours ago
$484
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Aug 20 from Des Moines Intl. to Lambert-St. Louis Intl., returning Sat, Aug 23, priced at $484 found 17 hours ago

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the MDH airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Williamson County Regional Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $99, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $99 right now, why wait?

Chester Flight Information
Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Roundtrip price
$98

Last Minute Hotel Deals in Chester

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street, Chester, IL
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
8.4/10 Very Good! (328 reviews)
"just a nice clean place to stay, not very far from shooting complex at Sparta"

Reviewed on Aug 4, 2025

Get rates
Baymont by Wyndham Chester IL
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
Stay at this 3-star business-friendly hotel in Festus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (828 reviews)
"Truly amazed by the speed of check-in. The clerk on duty had her paperwork all ready, spread out on a desk. She seemed to guess which guest I was and just handed over the document to initial. Perfect efficiency! Also, she was pleasant. The lobby, stairs and hallways had been recently upgraded. Room ..."

Reviewed on Jul 21, 2025

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La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Postcard Cabins St. Francois

Postcard Cabins St. Francois

2 out of 5
7555 State Hwy Y, French Village, MO
Stay at this cabin in French Village. Enjoy free parking, patios, and climate control.
9.8/10 Exceptional! (25 reviews)
"Sweet cabin"

Reviewed on Aug 12, 2025

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Postcard Cabins St. Francois
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St, Perryville, MO
Book a stay at this business-friendly hotel in Perryville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (495 reviews)
"I thought that this property had just been constructed as everything was brilliant. Staff was super nice and knowledgeable about the area. 100% would recommend to anyone needing to visit the area or passing through."

Reviewed on Aug 11, 2025

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Holiday Inn Express & Suites Perryville by IHG
Super 8 by Wyndham Perryville

Super 8 by Wyndham Perryville

2 out of 5
1119 Vincent Dr, Perryville, MO
Book a stay at this business-friendly motel in Perryville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (894 reviews)
"Great"

Reviewed on Aug 14, 2025

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Super 8 by Wyndham Perryville
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
Book a stay at this business-friendly hotel in Ste Genevieve. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (588 reviews)
Trip to Ste Genevieve
"The beds were firm, which I like and very clean. Plenty of towels from day one. Internet was great and tv options were great too. Front desk associates did a great job."

Reviewed on Aug 12, 2025

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Microtel Inn & Suites by Wyndham Sainte Genevieve
Festus Inn

Festus Inn

2 out of 5
1200 W Gannon Dr, Festus, MO
Stay at this hotel in Festus. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jorkerst Memorial Park and Sunset Park are located ...
5.4/10 (28 reviews)
"Very nice"

Reviewed on Aug 8, 2025

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Festus Inn
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
Book a stay at this business-friendly hotel in Sparta. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (345 reviews)
"Great staff, great facility."

Reviewed on Jul 21, 2025

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Holiday Inn Express Hotel & Suites Sparta by IHG
See all 145 properties in Chester
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.