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Winchester

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Winchester Flights as Low as $237

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

Delta
Mon, Nov 2 - Mon, Nov 9
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 2 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Mon, Nov 9, priced at $237 found 1 day ago
Frontier Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $258 found 1 day ago
Frontier Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $261 found 1 day ago
Delta
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $262 found 1 day ago
United
Thu, Aug 20 - Tue, Aug 25
MCI
Kansas City Intl.
PIA
Greater Peoria Regional
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 20 from Kansas City Intl. to Greater Peoria Regional, returning Tue, Aug 25, priced at $285 found 1 day ago
Delta
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $287 found 1 day ago
Frontier Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $291 found 1 day ago
United
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select United flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $292 found 1 day ago
Frontier Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $294 found 1 day ago
Delta
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $302 found 1 day ago
United
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$316 Roundtrip, found 1 day ago
$316
Roundtrip
found 1 day ago
Select United flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $316 found 1 day ago
United
Thu, Aug 6 - Mon, Aug 10
IAH
George Bush Intercontinental
PIA
Greater Peoria Regional
$329 Roundtrip, found 2 hours ago
$329
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Aug 6 from George Bush Intercontinental to Greater Peoria Regional, returning Mon, Aug 10, priced at $329 found 2 hours ago
United
Sat, Aug 22 - Mon, Aug 24
MCI
Kansas City Intl.
STL
Lambert-St. Louis Intl.
$334 Roundtrip, found 3 days ago
$334
Roundtrip
found 3 days ago
Select United flight, departing Sat, Aug 22 from Kansas City Intl. to Lambert-St. Louis Intl., returning Mon, Aug 24, priced at $334 found 3 days ago
American Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
STL
Lambert-St. Louis Intl.
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Lambert-St. Louis Intl., returning Sun, Nov 8, priced at $356 found 1 day ago
United
Tue, Sep 15 - Sun, Sep 27
IAH
George Bush Intercontinental
DEC
Decatur
$384 Roundtrip, found 15 hours ago
$384
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Sep 15 from George Bush Intercontinental to Decatur, returning Sun, Sep 27, priced at $384 found 15 hours ago
American Airlines
Thu, Aug 13 - Mon, Aug 17
IAH
George Bush Intercontinental
BRL
Southeast Iowa Regional
$386 Roundtrip, found 5 days ago
$386
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Aug 13 from George Bush Intercontinental to Southeast Iowa Regional, returning Mon, Aug 17, priced at $386 found 5 days ago

Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester 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 Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Winchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester 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 IJX airport.

What is the cheapest month to fly to Winchester?

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 Winchester are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

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

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $237, 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 Winchester?

The trick to saving a stack of cash on your flight to Winchester? 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 $237 right now, why wait?

Winchester Flight Information
Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Roundtrip price
$56

Last Minute Hotel Deals in Winchester

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (817 reviews)
"Great, helpful staff. Was clean but had large stain on carpet in our room."

Reviewed on Jul 8, 2026

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Best Western Jacksonville Inn
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (710 reviews)
"Very nice welcoming front desk staff. Pool and pool table, plus some casino style gaming (I think. We didn't do this). Typical chain hotel but nothing broken or worn out! Hot breakfast."

Reviewed on Jul 6, 2026

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Sleep Inn & Suites South Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museum ...
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Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (486 reviews)
"No"

Reviewed on Jul 14, 2026

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Quality Inn Jacksonville near I-72
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 out of 5
2501 Holliday Lane Jacksonville IL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museum ...
7.8/10 Good! (482 reviews)
"The room was disgusting. Dirty floors and furniture, broken tiles and dirty bathroom, dirty walls, odor of bleach and chlorine so strong I couldn’t sleep. Laid on a small piece of the bed the first night, came back the next day at 5 and cancelled the next two nights. Room 209"

Reviewed on Jul 15, 2026

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Holiday Inn Express Hotel & Suites Jacksonville by IHG
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave Jacksonville IL
Book a stay at this business-friendly motel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (654 reviews)
"Property was dated."

Reviewed on Jul 8, 2026

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Super 8 by Wyndham Jacksonville
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (529 reviews)
"Clean rooms and friendly staff."

Reviewed on Jun 26, 2026

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Hampton Inn Jacksonville
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
Stay at this hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County ...
9.2/10 Wonderful! (365 reviews)
"A must stop for any history lover. Beautiful building! AC was sufficient, parking was easy even though the hotel is on a main road. Our room was in the middle of the building so we didn’t hear much road noise. And yes it’s on a main road, but this is a small town so the traffic isn’t anything major. ..."

Reviewed on Jul 7, 2026

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William Watson Hotel
See all 72 properties in Winchester
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.