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Winchester

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Winchester Flights as Low as $90

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

Frontier Airlines
Sun, May 25 - Wed, May 28
MCO
Orlando Intl.
IND
Indianapolis Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, May 25 from Orlando Intl. to Indianapolis Intl., returning Wed, May 28, priced at $90 found 5 days ago
Spirit Airlines
Sat, May 17 - Sun, May 18
MCO
Orlando Intl.
IND
Indianapolis Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 17 from Orlando Intl. to Indianapolis Intl., returning Sun, May 18, priced at $92 found 5 days ago
American Airlines
Wed, Aug 27 - Sat, Aug 30
CLT
Charlotte-Douglas Intl.
IND
Indianapolis Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 27 from Charlotte-Douglas Intl. to Indianapolis Intl., returning Sat, Aug 30, priced at $139 found 2 days ago
Frontier Airlines
Sat, May 31 - Sat, May 31
ORD
O'Hare Intl.
IND
Indianapolis Intl.
$172 Roundtrip, found 20 hours ago
$172
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from O'Hare Intl. to Indianapolis Intl., returning Sat, May 31, priced at $172 found 20 hours ago
Spirit Airlines
Thu, May 22 - Sat, May 24
RIC
Richmond Intl.
IND
Indianapolis Intl.
$173 Roundtrip, found 18 hours ago
$173
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, May 22 from Richmond Intl. to Indianapolis Intl., returning Sat, May 24, priced at $173 found 18 hours ago
Delta
Tue, Aug 26 - Wed, Sep 3
CLT
Charlotte-Douglas Intl.
IND
Indianapolis Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 26 from Charlotte-Douglas Intl. to Indianapolis Intl., returning Wed, Sep 3, priced at $177 found 2 days ago
United
Thu, Jun 5 - Mon, Jun 9
ORD
O'Hare Intl.
IND
Indianapolis Intl.
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select United flight, departing Thu, Jun 5 from O'Hare Intl. to Indianapolis Intl., returning Mon, Jun 9, priced at $182 found 6 days ago
American Airlines
Tue, Jun 10 - Sat, Jun 14
MCI
Kansas City Intl.
IND
Indianapolis Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 10 from Kansas City Intl. to Indianapolis Intl., returning Sat, Jun 14, priced at $187 found 1 day ago
Frontier Airlines
Wed, May 14 - Fri, May 16
SFO
San Francisco Intl.
IND
Indianapolis Intl.
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 14 from San Francisco Intl. to Indianapolis Intl., returning Fri, May 16, priced at $202 found 3 days ago
Spirit Airlines
Thu, May 22 - Wed, May 28
IAH
George Bush Intercontinental
IND
Indianapolis Intl.
$204 Roundtrip, found 3 hours ago
$204
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, May 22 from George Bush Intercontinental to Indianapolis Intl., returning Wed, May 28, priced at $204 found 3 hours ago
Bargain Flight
Thu, Aug 21 - Sun, Aug 24
BOS
Logan Intl.
IND
Indianapolis Intl.
$235 Roundtrip, found 17 hours ago
$235
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Thu, Aug 21 from Logan Intl. to Indianapolis Intl., returning Sun, Aug 24, priced at $235 found 17 hours ago
Alaska Airlines
Sat, May 17 - Wed, May 21
SFO
San Francisco Intl.
IND
Indianapolis Intl.
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, May 17 from San Francisco Intl. to Indianapolis Intl., returning Wed, May 21, priced at $240 found 3 days ago
Bargain Flight
Sat, May 10 - Sun, May 11
SAV
Savannah - Hilton Head Intl.
IND
Indianapolis Intl.
$264 Roundtrip, found 21 hours ago
$264
Roundtrip
found 21 hours ago
Select Bargain Flight flight, departing Sat, May 10 from Savannah - Hilton Head Intl. to Indianapolis Intl., returning Sun, May 11, priced at $264 found 21 hours ago
Air Canada
Sat, Jun 7 - Sat, Jun 7
YUL
Pierre Elliott Trudeau Intl.
IND
Indianapolis Intl.
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Jun 7 from Pierre Elliott Trudeau Intl. to Indianapolis Intl., returning Sat, Jun 7, priced at $330 found 1 day ago
Air Canada
Fri, Jun 6 - Tue, Jun 10
YUL
Pierre Elliott Trudeau Intl.
IND
Indianapolis Intl.
$332 Roundtrip, found 1 day ago
$332
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Jun 6 from Pierre Elliott Trudeau Intl. to Indianapolis Intl., returning Tue, Jun 10, priced at $332 found 1 day ago
WestJet
Wed, Jun 4 - Wed, Jun 4
YUL
Pierre Elliott Trudeau Intl.
IND
Indianapolis Intl.
$386 Roundtrip, found 1 day ago
$386
Roundtrip
found 1 day ago
Select WestJet flight, departing Wed, Jun 4 from Pierre Elliott Trudeau Intl. to Indianapolis Intl., returning Wed, Jun 4, priced at $386 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 May, 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 $90, 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 $90 right now, why wait?

Winchester Flight Information
Destination airport
Indianapolis Intl.
Destination airport IATA code
IND
Roundtrip price
$89

Last Minute Hotel Deals in Winchester

Randolph Inn and Suites
Randolph Inn and Suites
2.5 out of 5
890 E Washington, Winchester, IN
The price is $121 per night from Apr 28 to Apr 29
$121
includes taxes & fees
Apr 28 - Apr 29
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions ...
8.8/10 Excellent! (215 reviews)
"When I booked our room I did not realize there was a motel section of rooms and then the Inn rooms. They were nice and got us a room at the Inn but it was much more expensive, not a pleasant surprise!"

Reviewed on Apr 11, 2025

Randolph Inn and 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
The price is $72 per night from May 4 to May 5
$72
includes taxes & fees
May 4 - May 5
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 (800 reviews)
"It was great!! The room was very comfortable! Perfect for mobility challenged people. Front desk very friendly!"

Reviewed on Apr 21, 2025

Days Inn by Wyndham Muncie -Ball State University
Baymont by Wyndham Richmond I-70
Baymont by Wyndham Richmond I-70
2.5 out of 5
912 Mendleson Dr, Richmond, IN
The price is $78 per night from May 11 to May 12
$78
includes taxes & fees
May 11 - May 12
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 ...
8/10 Very Good! (999 reviews)
"We liked the fact that the property was easy on and easy off of the main highway. Amiya, the young lady at the counter was very courteous and friendly when we called to confirm our reservation. When we arrived, Amiya was very kind in trying to help us park our 26-foot U-Haul and car transport. We ..."

Reviewed on Apr 21, 2025

Baymont by Wyndham Richmond I-70
Comfort Inn & Suites Muncie
Comfort Inn & Suites Muncie
2.5 out of 5
3400 N Marleon Dr, Muncie, IN
The price is $90 per night from Apr 29 to Apr 30
$90
includes taxes & fees
Apr 29 - Apr 30
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 property ...
8.4/10 Very Good! (651 reviews)
"Room was okay good for what we needed while we were there. Pool a little cloudy. Breakfast was great."

Reviewed on Apr 16, 2025

Comfort Inn & Suites Muncie
Holiday Inn Express Hotel & Suites Muncie by IHG
Holiday Inn Express Hotel & Suites Muncie by IHG
2.5 out of 5
4201 W Bethel Ave, Muncie, IN
The price is $143 per night from May 4 to May 5
$143
includes taxes & fees
May 4 - May 5
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! (563 reviews)
"Friendly front desk & helpful"

Reviewed on Apr 20, 2025

Holiday Inn Express Hotel & Suites Muncie by IHG
Fairfield Inn by Marriott Muncie
Fairfield Inn by Marriott Muncie
2.5 out of 5
4011 W Bethel Ave, Muncie, IN
The price is $104 per night from May 4 to May 5
$104
includes taxes & fees
May 4 - May 5
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 ...
8/10 Very Good! (697 reviews)
"Everything was just fine clean and the workers were very helpful and nice I will come again 🙂"

Reviewed on Apr 21, 2025

Fairfield Inn by Marriott Muncie
Comfort Suites
Comfort Suites
2.5 out of 5
421 Commerce Road, Richmond, IN
The price is $116 per night from May 11 to May 12
$116
includes taxes & fees
May 11 - May 12
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! (464 reviews)
"Indoor Pool was closed the whole time."

Reviewed on Apr 20, 2025

Comfort Suites
Quality Inn and Conference Center
Quality Inn and Conference Center
2.5 out of 5
5501 National Rd E, Richmond, IN
The price is $57 per night from May 4 to May 5
$57
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.8/10 (1,002 reviews)
"Outside looks nice and front desk, sheets on bed inside out. Need a cleaner Shower curtain."

Reviewed on Apr 12, 2025

Quality Inn and Conference Center
See all 108 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.