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Winchester

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Winchester Flights as Low as $68

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

Frontier Airlines
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $68 found 2 hours ago
Frontier Airlines
Mon, Sep 14 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$80 Roundtrip, found 2 hours ago
$80
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $80 found 2 hours ago
Frontier Airlines
Wed, Sep 16 - Fri, Oct 2
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$103 Roundtrip, found 2 hours ago
$103
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Fri, Oct 2, priced at $103 found 2 hours ago
Frontier Airlines
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$113 Roundtrip, found 2 hours ago
$113
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $113 found 2 hours ago
Frontier Airlines
Mon, Sep 14 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$115 Roundtrip, found 2 hours ago
$115
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $115 found 2 hours ago
Frontier Airlines
Fri, Sep 11 - Wed, Sep 16
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$123 Roundtrip, found 14 hours ago
$123
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Denver Intl. to Lambert-St. Louis Intl., returning Wed, Sep 16, priced at $123 found 14 hours ago
Frontier Airlines
Fri, Oct 30 - Fri, Nov 13
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$124 Roundtrip, found 4 days ago
$124
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Oct 30 from Denver Intl. to Lambert-St. Louis Intl., returning Fri, Nov 13, priced at $124 found 4 days ago
Frontier Airlines
Mon, Sep 14 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $125 found 2 hours ago
Frontier Airlines
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $128 found 2 hours ago
Southwest Airlines
Wed, Sep 16 - Mon, Sep 28
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Mon, Sep 28, priced at $177 found 2 hours ago
United
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $177 found 2 hours ago
Delta
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $197 found 2 hours ago
American Airlines
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Sep 26, priced at $197 found 2 hours ago
Frontier Airlines
Wed, Nov 11 - Thu, Nov 12
ONT
Ontario Intl. Airport
STL
Lambert-St. Louis Intl.
$278 Roundtrip, found 16 hours ago
$278
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Ontario Intl. Airport to Lambert-St. Louis Intl., returning Thu, Nov 12, priced at $278 found 16 hours ago
Alaska Airlines
Mon, Nov 16 - Tue, Nov 17
ONT
Ontario Intl. Airport
STL
Lambert-St. Louis Intl.
$357 Roundtrip, found 7 hours ago
$357
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Mon, Nov 16 from Ontario Intl. Airport to Lambert-St. Louis Intl., returning Tue, Nov 17, priced at $357 found 7 hours ago
United
Wed, Aug 26 - Wed, Sep 2
DEN
Denver Intl.
PIA
Greater Peoria Regional
$359 Roundtrip, found 2 days ago
$359
Roundtrip
found 2 days ago
Select United flight, departing Wed, Aug 26 from Denver Intl. to Greater Peoria Regional, returning Wed, Sep 2, priced at $359 found 2 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 September, 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 $68, 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 $68 right now, why wait?

Winchester Flight Information
Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Roundtrip price
$68

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! (736 reviews)
"Hotel was very clean and staff were pleasant. Hot breakfast a plus. Bike machine in the fitness room was broken and the bed was very firm. It was a nice stay overall."

Reviewed on Aug 16, 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 ...
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Best Western Jacksonville Inn
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 parking, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very Good! (662 reviews)
"Toxic A/C fumes! Avoid rm 114! I smelled it as soon as I entered but was too much to ask to change rooms. I might have gotten somewhat used to it until waking up at 3:00 am to the same severity of smell as when we first entered. Figured out every time the a/c kicked on we were getting a new shot ..."

Reviewed on Aug 17, 2026

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Super 8 by Wyndham 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 Museum ...
7.8/10 Good! (492 reviews)
"The hotel room had chipped and peeling paint. The carpet was stained. The shampoo and hand soap wasn’t filled up. The furniture was peeling on the edges and the television volume wasn’t clear."

Reviewed on Aug 17, 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 Museum ...
7.8/10 Good! (41 reviews)
"Clean and great staff! I love this place!"

Reviewed on Aug 21, 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! (500 reviews)
"room 306: toilet not bolted down. bathroom floor tiles loose. TP dispenser broken on one side, other side dispensed single sheets of the flimsiest paper I have seen yet. Bring your own. One ice machine was working in building the evening we arrived. It broke next day; none worked rest of the week. ..."

Reviewed on Aug 22, 2026

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Quality Inn Jacksonville near I-72
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! (536 reviews)
"Wonderful stay and the staff was so kind. Great breakfast too!"

Reviewed on Aug 16, 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! (368 reviews)
"Our room was not well maintained. The carpet was dirty and frayed. The bathroom tile needs maintenance"

Reviewed on Aug 6, 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.