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Winchester

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Winchester Flights as Low as $177

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

Frontier Airlines
Fri, Sep 11 - Mon, Sep 14
BWI
Baltimore Washington Intl. Thurgood Marshall
IND
Indianapolis Intl.
$177 Roundtrip, found 16 hours ago
$177
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Baltimore Washington Intl. Thurgood Marshall to Indianapolis Intl., returning Mon, Sep 14, priced at $177 found 16 hours ago
Bargain Flight
Fri, Sep 18 - Sat, Sep 19
MSP
Minneapolis - St. Paul Intl.
IND
Indianapolis Intl.
$206 Roundtrip, found 2 days ago
$206
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Sep 18 from Minneapolis - St. Paul Intl. to Indianapolis Intl., returning Sat, Sep 19, priced at $206 found 2 days ago
Bargain Flight
Wed, Aug 12 - Wed, Aug 19
DCA
Ronald Reagan Washington National
IND
Indianapolis Intl.
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Aug 12 from Ronald Reagan Washington National to Indianapolis Intl., returning Wed, Aug 19, priced at $207 found 2 days ago
Frontier Airlines
Sat, Sep 12 - Wed, Sep 30
RDU
Raleigh - Durham Intl.
IND
Indianapolis Intl.
$210 Roundtrip, found 16 hours ago
$210
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Raleigh - Durham Intl. to Indianapolis Intl., returning Wed, Sep 30, priced at $210 found 16 hours ago
Frontier Airlines
Tue, Nov 3 - Mon, Nov 16
MIA
Miami Intl.
IND
Indianapolis Intl.
$232 Roundtrip, found 23 hours ago
$232
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Nov 3 from Miami Intl. to Indianapolis Intl., returning Mon, Nov 16, priced at $232 found 23 hours ago
Frontier Airlines
Tue, Aug 25 - Wed, Sep 9
IAH
George Bush Intercontinental
IND
Indianapolis Intl.
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from George Bush Intercontinental to Indianapolis Intl., returning Wed, Sep 9, priced at $244 found 3 days ago
Delta
Wed, Sep 2 - Tue, Sep 22
BWI
Baltimore Washington Intl. Thurgood Marshall
IND
Indianapolis Intl.
$267 Roundtrip, found 1 day ago
$267
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 2 from Baltimore Washington Intl. Thurgood Marshall to Indianapolis Intl., returning Tue, Sep 22, priced at $267 found 1 day ago
American Airlines
Tue, Sep 29 - Wed, Oct 14
BWI
Baltimore Washington Intl. Thurgood Marshall
IND
Indianapolis Intl.
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 29 from Baltimore Washington Intl. Thurgood Marshall to Indianapolis Intl., returning Wed, Oct 14, priced at $267 found 6 days ago
American Airlines
Wed, Aug 12 - Wed, Aug 19
DCA
Ronald Reagan Washington National
IND
Indianapolis Intl.
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 12 from Ronald Reagan Washington National to Indianapolis Intl., returning Wed, Aug 19, priced at $277 found 2 days ago
Sun Country Airlines
Wed, Aug 5 - Thu, Aug 6
MSP
Minneapolis - St. Paul Intl.
IND
Indianapolis Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Wed, Aug 5 from Minneapolis - St. Paul Intl. to Indianapolis Intl., returning Thu, Aug 6, priced at $291 found 1 day ago
Delta
Sat, Sep 19 - Tue, Sep 22
DAL
Love Field
IND
Indianapolis Intl.
$301 Roundtrip, found 20 hours ago
$301
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Sep 19 from Love Field to Indianapolis Intl., returning Tue, Sep 22, priced at $301 found 20 hours ago
Southwest Airlines
Mon, Sep 21 - Fri, Sep 25
DAL
Love Field
IND
Indianapolis Intl.
$312 Roundtrip, found 20 hours ago
$312
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Love Field to Indianapolis Intl., returning Fri, Sep 25, priced at $312 found 20 hours ago
United
Thu, Sep 24 - Sun, Oct 4
SJO
Juan Santamaría Intl.
IND
Indianapolis Intl.
$333 Roundtrip, found 21 hours ago
$333
Roundtrip
found 21 hours ago
Select United flight, departing Thu, Sep 24 from Juan Santamaría Intl. to Indianapolis Intl., returning Sun, Oct 4, priced at $333 found 21 hours ago
Accessrail
Tue, Nov 3 - Sat, Nov 21
EKW
Miami Central Brightline Train Station
IND
Indianapolis Intl.
$469 Roundtrip, found 23 hours ago
$469
Roundtrip
found 23 hours ago
Select Accessrail flight, departing Tue, Nov 3 from Miami Central Brightline Train Station to Indianapolis Intl., returning Sat, Nov 21, priced at $469 found 23 hours ago
United
Wed, Aug 5 - Sun, Aug 30
LIR
Daniel Oduber Intl.
IND
Indianapolis Intl.
$477 Roundtrip, found 21 hours ago
$477
Roundtrip
found 21 hours ago
Select United flight, departing Wed, Aug 5 from Daniel Oduber Intl. to Indianapolis Intl., returning Sun, Aug 30, priced at $477 found 21 hours ago
Accessrail
Fri, Nov 20 - Sun, Nov 29
AVT
Aventura Brightline Train Station
IND
Indianapolis Intl.
$614 Roundtrip, found 23 hours ago
$614
Roundtrip
found 23 hours ago
Select Accessrail flight, departing Fri, Nov 20 from Aventura Brightline Train Station to Indianapolis Intl., returning Sun, Nov 29, priced at $614 found 23 hours 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 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 14 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 $177, 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 $177 right now, why wait?

Winchester Flight Information
Destination airport
Indianapolis Intl.
Destination airport IATA code
IND
Roundtrip price
$176

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! (269 reviews)
"My first stay at Randolph Suites. Service was absolutely excellent. Only disappointment was dirty floor in corner around lamp stand. No ceiling fan in bathroom. Water in shower never got hot. Again, great service provided by Cathy at the front desk."

Reviewed on Jul 27, 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 hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,000 reviews)
"I most likely will not stay here again. The reason behind this being my room was not upkept by housekeeping staff like it was promoted to be. My trash was not emptied once by a staff member, I had to take it out to the back myself, my linens were not changed and had dust/crumbs on them, my room was ..."

Reviewed on Jul 30, 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! (806 reviews)
"No"

Reviewed on Jul 27, 2026

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Comfort Suites Richmond East
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 ...
6.8/10 (948 reviews)
"Quick resolution to a mishap"

Reviewed on Jul 30, 2026

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Days Inn by Wyndham Muncie -Ball State University
Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center

3 out of 5
601 S High St Muncie IN
Book a stay at this business-friendly hotel in Muncie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (908 reviews)
"Stay"

Reviewed on Jul 26, 2026

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Courtyard Muncie at Horizon Convention Center
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 fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,001 reviews)
"Hotel needs to be updated. Kind of old."

Reviewed on Jul 30, 2026

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Motel 6 Richmond, IN
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 ...
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Baymont by Wyndham Muncie Near Ball State University
Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area

2 out of 5
3601 W Fox Ridge 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 helpful staff and the clean rooms ...
8/10 Very Good! (1,001 reviews)
"So disappointing. We have stayed at super 8 hotels in different areas.And they've been clean.The grounds well maintain. This hotel was so sad."

Reviewed on Jul 30, 2026

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Super 8 by Wyndham Muncie/Ball St. College Area
See all 139 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.