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Winchester

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Winchester Flights as Low as $127

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

Frontier Airlines
Mon, Apr 20 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $127 found 1 hour ago
Frontier Airlines
Thu, Apr 16 - Mon, May 4
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$129 Roundtrip, found 4 days ago
$129
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Denver Intl. to Lambert-St. Louis Intl., returning Mon, May 4, priced at $129 found 4 days ago
Frontier Airlines
Sat, Apr 18 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$131 Roundtrip, found 3 hours ago
$131
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $131 found 3 hours ago
Frontier Airlines
Thu, Apr 16 - Mon, Apr 27
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$134 Roundtrip, found 5 days ago
$134
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Denver Intl. to Lambert-St. Louis Intl., returning Mon, Apr 27, priced at $134 found 5 days ago
Frontier Airlines
Thu, Apr 16 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $136 found 2 days ago
Frontier Airlines
Sun, Apr 26 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Apr 26 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $138 found 1 hour ago
Frontier Airlines
Sat, Apr 18 - Tue, May 5
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Denver Intl. to Lambert-St. Louis Intl., returning Tue, May 5, priced at $139 found 1 day ago
Frontier Airlines
Thu, Apr 9 - Fri, Apr 24
TTN
Mercer
STL
Lambert-St. Louis Intl.
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Mercer to Lambert-St. Louis Intl., returning Fri, Apr 24, priced at $163 found 1 hour ago
Frontier Airlines
Tue, Apr 7 - Mon, Apr 13
PHL
Philadelphia Intl.
STL
Lambert-St. Louis Intl.
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 7 from Philadelphia Intl. to Lambert-St. Louis Intl., returning Mon, Apr 13, priced at $163 found 1 hour ago
Frontier Airlines
Thu, Apr 23 - Mon, May 11
SMF
Sacramento Intl.
STL
Lambert-St. Louis Intl.
$229 Roundtrip, found 22 hours ago
$229
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Sacramento Intl. to Lambert-St. Louis Intl., returning Mon, May 11, priced at $229 found 22 hours ago
United
Sat, Apr 18 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$247 Roundtrip, found 3 hours ago
$247
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Apr 18 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $247 found 3 hours ago
Delta
Mon, Apr 20 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$267 Roundtrip, found 1 hour ago
$267
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Apr 20 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $267 found 1 hour ago
American Airlines
Mon, Apr 20 - Sat, May 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$267 Roundtrip, found 1 hour ago
$267
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Apr 20 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, May 2, priced at $267 found 1 hour ago
United
Tue, Apr 7 - Thu, Apr 16
DEN
Denver Intl.
PIA
Greater Peoria Regional
$297 Roundtrip, found 4 days ago
$297
Roundtrip
found 4 days ago
Select United flight, departing Tue, Apr 7 from Denver Intl. to Greater Peoria Regional, returning Thu, Apr 16, priced at $297 found 4 days ago
Alaska Airlines
Thu, Apr 16 - Mon, May 4
SMF
Sacramento Intl.
STL
Lambert-St. Louis Intl.
$441 Roundtrip, found 1 hour ago
$441
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Thu, Apr 16 from Sacramento Intl. to Lambert-St. Louis Intl., returning Mon, May 4, priced at $441 found 1 hour ago
American Airlines
Fri, Apr 24 - Sun, Apr 26
PHL
Philadelphia Intl.
SPI
Abraham Lincoln Capital
$567 Roundtrip, found 3 days ago
$567
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Apr 24 from Philadelphia Intl. to Abraham Lincoln Capital, returning Sun, Apr 26, priced at $567 found 3 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 April, 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 $127, 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 $127 right now, why wait?

Winchester Flight Information
Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Roundtrip price
$144

Last Minute Hotel Deals in Winchester

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! (651 reviews)
Property well maintained. Staff is friendly. The fridge in our room was broken. Told staff and tyler had it fixed and our drinks were cold by the time we got off work. Great place to stay

Reviewed on Mar 21, 2026

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Sleep Inn & Suites South Jacksonville
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! (762 reviews)
Inexpensive, clean friendly place to sleep.

Reviewed on Mar 8, 2026

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Best Western Jacksonville Inn
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! (510 reviews)
The staff was great. We were worried staying at a pet-friendly hotel, but the property and our room looked and smelled fresh and clean. My only complaint is that the beds were too firm for my taste.

Reviewed on Mar 11, 2026

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Hampton Inn Jacksonville
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 Museam ...
7.8/10 Good! (453 reviews)
Everything was great except the pool was closed the night we stayed. Fortunately, the hotel arranged for guests to use the pool next door, which was a nice alternative. It was a pretty cold night, but the kids still had a good time—and that’s what mattered most.

Reviewed on Mar 21, 2026

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Holiday Inn Express Hotel & Suites Jacksonville by IHG
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 Museam ...
6/10 (4 reviews)
Room was great other than the mini fridge did not work.

Reviewed on Mar 14, 2026

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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! (448 reviews)
I will not be staying at this property again and I will 100% be back in this area. My room smelt of animal urine. My comforter had a large yellow stain on it that had a remnant urine smell. I switched it out for a different blanket. Luckily running the air conditioning a little helped to cycle the ...

Reviewed on Mar 9, 2026

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Quality Inn Jacksonville near I-72
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! (625 reviews)
Upon arrival girl at front desk we were first given a 2nd floor room. Asked where the elevator was and was told that they didn't have one Asked for main level which they had. I then asked where they kept the luggage cart. She wheeled out laundry basket on wheels. Then getting into bed and hear a ...

Reviewed on Feb 22, 2026

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Super 8 by Wyndham 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! (348 reviews)
Clean room, nice staff. Helpful when needing anything. The place had a nice rustic feel to it.

Reviewed on Dec 24, 2025

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William Watson Hotel
See all 43 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.