Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $68

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

Frontier Airlines
Frontier Airlines
Spirit Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Spirit Airlines
Spirit Airlines
Frontier Airlines
Frontier Airlines
United
Frontier Airlines
American Airlines
Delta
United
Alaska Airlines

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 $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

Sleep Inn & Suites

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! (606 reviews)
Very clean

Reviewed on Oct 24, 2025

Sleep Inn & Suites
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! (730 reviews)
Na

Reviewed on Oct 29, 2025

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! (414 reviews)
Easy check in and out very personable and friendly staff

Reviewed on Oct 15, 2025

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! (431 reviews)
Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw.

Reviewed on Oct 11, 2025

Holiday Inn Express Hotel & Suites Jacksonville by IHG
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! (485 reviews)
My stay was great! Relaxing after a full day of work. But the best part of the trip was how wonderful your staff treated me! Madison was awesome and so kind! She offered great advice on local sites, restaurants and answered my queries with great enthusiasm. I missed her on her days off! So glad she ...

Reviewed on Oct 19, 2025

Hampton Inn Jacksonville
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 out of 5
1914 Southbrooke Road, 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 ...
7/10 Good! (846 reviews)
Great location. Newly remodeled room. Friendly staff.

Reviewed on Oct 9, 2025

Baymont by Wyndham 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! (609 reviews)
Good service

Reviewed on Oct 19, 2025

Super 8 by Wyndham Jacksonville
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid ...
8.6/10 Excellent! (139 reviews)
Room climate was fine, haven't had the breakfast yet.

Reviewed on Sep 27, 2025

Green Acres 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.