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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 IND 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 , 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  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 Delaware County 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 , 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  right now, why wait?

Winchester Flight Information
Destination airport
Indianapolis Intl.
Destination airport IATA code
IND
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Number of airlines serving
4
Roundtrip price
$198
Popular airline
American Airlines

Last Minute Hotel Deals in Winchester

Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington Winchester IN
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Winchester Golf Club and Winchester Speedway are located ...
8.8/10 Excellent! (243 reviews)
Breakfast was good.the staff very friendly and the other hotel guest very friendly

Reviewed on Oct 28, 2025

Randolph Inn and Suites
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr Richmond IN
Stay at this inn in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,018 reviews)
Clean comfortable room, convenient location

Reviewed on Nov 30, 2025

Baymont by Wyndham Richmond I-70
Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University

2.5 out of 5
3400 North Chadam Lane Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
5.6/10 (1,000 reviews)
Very nice

Reviewed on Nov 21, 2025

Baymont by Wyndham Muncie Near Ball State University
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road Richmond IN
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (647 reviews)
Room was very clean. The staff was very friendly and helpful. Breakfast was hot and tasty.

Reviewed on Nov 29, 2025

Comfort Suites
Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
3509 N Everbrook Ln Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
6.6/10 (884 reviews)
Good price, clean. No elevator, but was on 1st floor, but still weird.

Reviewed on Nov 29, 2025

Days Inn by Wyndham Muncie -Ball State University
Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70

2.5 out of 5
533 W Eaton Pike Richmond IN
Stay at this hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,000 reviews)
We were very pleased with our stay. The place felt new and was so nicely decorated for the holiday! It felt cozy and comfortable. Breakfast was hot and tasty, my girls loved making their own waffles (bonus seasonal flavor!). I enjoyed the biscuits and gravy and fluffy scrambled eggs. We had a peaceful ...

Reviewed on Nov 29, 2025

Best Western Plus Richmond Indiana I-70
Muncie Place Hotel & Suites

Muncie Place Hotel & Suites

2.5 out of 5
4201 W Bethel Ave Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (598 reviews)
This hotel is nice. Location is close to university, shopping, restaurants. Has an outdoor patio area to sit at. Pool area and fitness room was nice. Hotel and parking lot was very clean. Staff was wonderful especially Ms Sonda and Ms Jama on the breakfast area. Not only were they both friendly, ...

Reviewed on Nov 30, 2025

Muncie Place Hotel & Suites
Hampton Inn & Suites Muncie

Hampton Inn & Suites Muncie

2.5 out of 5
4220 W Bethel Ave Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (878 reviews)
Clean room and bathroom. Bed was very comfortable. Vent fan in bathroom not operating but other than that, very pleased.

Reviewed on Nov 8, 2025

Hampton Inn & Suites Muncie
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.