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Winchester

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Winchester Flights as Low as $93

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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 February, 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 $93, 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 $93 right now, why wait?

Winchester Flight Information
Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Roundtrip price
$172

Last Minute Hotel Deals in Winchester

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 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 ...
9.2/10 Wonderful! (629 reviews)
Arrived late evening for a one-night stay and found the room to be clean and comfortable. Breakfast was good. Have stayed in several Sleep Inn & Suites in the past year and have always found them to be wonderful! Staff is always nice and facilities clean and comfortable. Best option I have found ...

Reviewed on Jan 20, 2026

Sleep Inn & Suites South 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! (502 reviews)
Clean room. Great friendly staff.

Reviewed on Jan 17, 2026

Hampton Inn Jacksonville
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! (619 reviews)
It was a fantastic stay!

Reviewed on Dec 31, 2025

Super 8 by Wyndham 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! (753 reviews)
Check-in was easy! No hassles! Room is clean and the TV works😊

Reviewed on Jan 7, 2026

Best Western Jacksonville Inn
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. ...
7.6/10 Good! (443 reviews)
The pool was warm!! The room was nice and clean .. The water pressure in the showers along with the soap that was free was amazing .. for a cheap rate you couldn’t beat this hotel

Reviewed on Jan 17, 2026

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 Museam ...
7.6/10 Good! (447 reviews)
Clean room and great breakfast.

Reviewed on Jan 19, 2026

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Villa DeWolf

Villa DeWolf

4 out of 5
876 W State St Jacksonville IL
Book a stay at this business-friendly B&B in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Governor Duncan Mansion and ...
9.8/10 Exceptional! (11 reviews)
nice room quiet

Reviewed on Nov 18, 2025

Villa DeWolf
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! (254 reviews)
Clean room, nice staff. Helpful when needing anything. The place had a nice rustic feel to it.

Reviewed on Dec 24, 2025

William Watson Hotel
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.