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Winchester

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Winchester Flights as Low as $115

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

Frontier Airlines
Thu, Apr 16 - Mon, Apr 20
DFW
Dallas-Fort Worth Intl.
IND
Indianapolis Intl.
$115 Roundtrip, found 13 hours ago
$115
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Dallas-Fort Worth Intl. to Indianapolis Intl., returning Mon, Apr 20, priced at $115 found 13 hours ago
Spirit Airlines
Tue, May 12 - Tue, May 19
EWR
Newark Liberty Intl. Airport
IND
Indianapolis Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, May 12 from Newark Liberty Intl. Airport to Indianapolis Intl., returning Tue, May 19, priced at $121 found 1 day ago
Spirit Airlines
Wed, May 13 - Tue, May 19
EWR
Newark Liberty Intl. Airport
IND
Indianapolis Intl.
$129 Roundtrip, found 3 hours ago
$129
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, May 13 from Newark Liberty Intl. Airport to Indianapolis Intl., returning Tue, May 19, priced at $129 found 3 hours ago
Frontier Airlines
Thu, Apr 16 - Mon, Apr 20
DFW
Dallas-Fort Worth Intl.
IND
Indianapolis Intl.
$133 Roundtrip, found 13 hours ago
$133
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Dallas-Fort Worth Intl. to Indianapolis Intl., returning Mon, Apr 20, priced at $133 found 13 hours ago
Spirit Airlines
Sat, May 2 - Tue, May 5
IAH
George Bush Intercontinental
IND
Indianapolis Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 2 from George Bush Intercontinental to Indianapolis Intl., returning Tue, May 5, priced at $138 found 1 day ago
Frontier Airlines
Sat, May 2 - Sat, May 16
PHL
Philadelphia Intl.
IND
Indianapolis Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from Philadelphia Intl. to Indianapolis Intl., returning Sat, May 16, priced at $144 found 1 day ago
Frontier Airlines
Sat, May 2 - Sat, May 16
TTN
Mercer
IND
Indianapolis Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from Mercer to Indianapolis Intl., returning Sat, May 16, priced at $144 found 1 day ago
Frontier Airlines
Sun, Apr 19 - Wed, May 6
SAN
San Diego Intl.
IND
Indianapolis Intl.
$190 Roundtrip, found 21 hours ago
$190
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sun, Apr 19 from San Diego Intl. to Indianapolis Intl., returning Wed, May 6, priced at $190 found 21 hours ago
Bargain Flight
Sat, Jul 4 - Tue, Jul 7
DCA
Ronald Reagan Washington National
IND
Indianapolis Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Sat, Jul 4 from Ronald Reagan Washington National to Indianapolis Intl., returning Tue, Jul 7, priced at $197 found 1 hour ago
American Airlines
Thu, Jun 4 - Sat, Jun 6
DCA
Ronald Reagan Washington National
IND
Indianapolis Intl.
$254 Roundtrip, found 5 hours ago
$254
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Jun 4 from Ronald Reagan Washington National to Indianapolis Intl., returning Sat, Jun 6, priced at $254 found 5 hours ago
Delta
Sat, May 2 - Mon, May 4
IAH
George Bush Intercontinental
IND
Indianapolis Intl.
$267 Roundtrip, found 3 hours ago
$267
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, May 2 from George Bush Intercontinental to Indianapolis Intl., returning Mon, May 4, priced at $267 found 3 hours ago
Delta
Sat, Apr 18 - Sat, Apr 18
DAL
Love Field
IND
Indianapolis Intl.
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 18 from Love Field to Indianapolis Intl., returning Sat, Apr 18, priced at $303 found 2 days ago
Delta
Sat, Apr 25 - Sat, May 9
PSP
Palm Springs Intl.
IND
Indianapolis Intl.
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Apr 25 from Palm Springs Intl. to Indianapolis Intl., returning Sat, May 9, priced at $334 found 1 day ago
Alaska Airlines
Thu, Apr 23 - Tue, May 12
PSP
Palm Springs Intl.
IND
Indianapolis Intl.
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Apr 23 from Palm Springs Intl. to Indianapolis Intl., returning Tue, May 12, priced at $349 found 1 day ago
American Airlines
Sat, May 2 - Sat, May 16
CLD
McClellan-Palomar
IND
Indianapolis Intl.
$351 Roundtrip, found 21 hours ago
$351
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, May 2 from McClellan-Palomar to Indianapolis Intl., returning Sat, May 16, priced at $351 found 21 hours ago
Hawaiian Airlines
Mon, Apr 6 - Tue, Apr 14
PSP
Palm Springs Intl.
IND
Indianapolis Intl.
$709 Roundtrip, found 1 day ago
$709
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, Apr 6 from Palm Springs Intl. to Indianapolis Intl., returning Tue, Apr 14, priced at $709 found 1 day 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 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 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 15 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 $115, 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 $115 right now, why wait?

Winchester Flight Information
Destination airport
Indianapolis Intl.
Destination airport IATA code
IND
Roundtrip price
$115

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 ...
9/10 Wonderful! (253 reviews)
There are 2 properties, a motel and a hotel. This is NOT clear when you are making a reservation thru Expedia. The motel is older. The beds are super low. The shower is small. You have to drive to the hotel to eat breakfast and check in/out. The breakfast was good with hot items. The pool was closed ...

Reviewed on Mar 30, 2026

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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 ...
8.4/10 Very Good! (1,005 reviews)
Looking from the outside, I was not impressed but my room was clean, the air conditioner kept the room cool and the breakfast was excellent, especially for the price I paid. I would definitely stay here again.

Reviewed on Mar 31, 2026

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Baymont by Wyndham Richmond I-70
Comfort Suites Richmond East

Comfort Suites Richmond East

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 ...
9.4/10 Exceptional! (700 reviews)
Fabulous hotel! The room was large & very clean. The queen Size bed was nice & comfortable.

Reviewed on Mar 30, 2026

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Comfort Suites Richmond East
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! (1,002 reviews)
The pool was indoor and warm. The breakfast was fresh and clean. Modern

Reviewed on Mar 21, 2026

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Best Western Plus Richmond Indiana I-70
Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University

2.5 out of 5
3400 N Marleon Dr 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. ...
8.4/10 Very Good! (773 reviews)
i did not eat breakfast there but i did get a chance to check it out and it looked good clean room parking was easy and safe

Reviewed on Mar 29, 2026

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Comfort Inn & Suites Muncie Near University
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! (612 reviews)
The staff members were amazing and professional. The place was clean and cozy. Breakfast was good 👍 A great place to visit while passing through.

Reviewed on Mar 23, 2026

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Muncie Place Hotel & Suites
Motel 6 Richmond, IN

Motel 6 Richmond, IN

2 out of 5
6030 National Road East Richmond IN
Stay at this motel in Richmond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,001 reviews)
Excellent staff. Right off of I70 and US40. Close to restaurants, grocery stores, and retail stores. Rooms have hard back/seat chairs. VERY uncomfortable. Need easy chairs in rooms. Bath tub floor slick when showering, needs anti slip strips to prevent possible guest slip/fall accident. My extended ...

Reviewed on Mar 30, 2026

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Motel 6 Richmond, IN
Fairfield Inn by Marriott Muncie

Fairfield Inn by Marriott Muncie

3 out of 5
4011 W Bethel Ave Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in ...
8.2/10 Very Good! (768 reviews)
Very clean everyone was very nice and helpful!

Reviewed on Mar 29, 2026

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Fairfield Inn by Marriott Muncie
See all 136 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.