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Stewart

$86+ Cheap flights from Indiana to New Windsor (SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SWF
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
1 adult, Economy
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Find flight deals from Indiana to Stewart

Cheapest flights from Indiana to Stewart
Explore the most affordable flight options available from Indiana to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Mon 12/1512:27 pmSWF - CVG
1 stop8h 59mMultiple Airlines
Deal found 11/16$247
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Sun 12/711:09 amSWF - CVG
1 stop13h 48mMultiple Airlines
Deal found 11/17$249
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:55 amSDF - SWF
1 stop23h 42mMultiple Airlines
Mon 12/85:44 pmSWF - SDF
1 stop23h 11mMultiple Airlines
Deal found 11/17$250
This Kiwi.com deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:18 pmDAY - SWF
1 stop21h 22mAllegiant Air
Mon 12/155:20 pmSWF - DAY
1 stop17h 38mAllegiant Air
Deal found 11/16$254
This Mytrip deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/712:50 pmCVG - SWF
2 stops22h 47mMultiple Airlines
Fri 12/1212:27 pmSWF - CVG
1 stop8h 59mMultiple Airlines
Deal found 11/16$257
This Kiwi.com deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:26 pmSDF - SWF
1 stop21h 14mAllegiant Air
Mon 12/155:20 pmSWF - SDF
1 stop23h 35mAllegiant Air
Deal found 11/16$260
This Mytrip deal was found by Cheapflights users on 11/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:29 pmFWA - SWF
1 stop16h 08mAllegiant Air
Fri 12/125:44 pmSWF - FWA
1 stop17h 30mAllegiant Air
Deal found 11/15$279
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Sun 12/1411:43 amSWF - CVG
1 stop11h 13mMultiple Airlines
Deal found 11/17$280
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:15 pmORD - SWF
1 stop13h 38mMultiple Airlines
Tue 12/2311:43 amSWF - ORD
1 stop23h 35mMultiple Airlines
Deal found 11/17$314
This Mytrip deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:30 amIND - SWF
2 stops30h 07mMultiple Airlines
Fri 12/196:56 pmSWF - IND
1 stop16h 37mMultiple Airlines
Deal found 11/16$319
This Kiwi.com deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:07 pmIND - SWF
1 stop21h 12mAllegiant Air
Fri 12/198:11 pmSWF - IND
1 stop27h 28mAllegiant Air
Deal found 11/16$322
This Kiwi.com deal was found by Cheapflights users on 11/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:07 pmIND - SWF
1 stop21h 12mAllegiant Air
Sat 12/209:45 amSWF - IND
1 stop13h 54mAllegiant Air
Deal found 11/15$334

Cheap flight deals from Indiana to Stewart

Keep the following information in mind while searching for Indiana to Stewart flight deals. Data was last updated November 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$212
(Mytrip)

One-way from

$86
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$323
Provider with most accurate pricing for Indianapolis-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Indianapolis-New York (NYC) flights.
Search Deals
From Indiana to New Windsor Stewart
Search Deals
One-way flight from Indiana to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 17, 2025.
Use the filters below to find and compare flights from Indiana to New Windsor that are best for you.

Fly from

Indiana

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/29

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 2/2

11:09 am-7:17 pm

1 stop9h 08m

$212

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/22

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/26

11:09 am-7:17 pm

1 stop9h 08m

$212

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 2/9

11:09 am-7:17 pm

1 stop9h 08m

$212

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 1/29

8:27 pm-5:12 pm

1 stop20h 45m

New Windsor Stewart

Mon 2/2

6:02 pm-5:32 pm

1 stop23h 30m

$215

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/8

12:48 pm-10:19 am

1 stop20h 31m

New Windsor Stewart

Sun 1/11

12:13 pm-5:52 pm

1 stop30h 39m

$219

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 1/8

3:28 pm-10:19 am

1 stop18h 51m

New Windsor Stewart

Mon 1/12

6:02 pm-5:32 pm

1 stop23h 30m

$228

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/11

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Mon 12/15

12:27 pm-9:26 pm

1 stop8h 59m

$241

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/4

12:50 pm-11:37 am

2 stops22h 47m

New Windsor Stewart

Fri 12/12

12:27 pm-9:26 pm

1 stop8h 59m

$246

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/4

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Sun 12/7

11:09 am-12:57 am

1 stop13h 48m

$249

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Sun 12/7

11:55 am-11:37 am

1 stop23h 42m

New Windsor Stewart

Mon 12/8

5:44 pm-4:55 pm

1 stop23h 11m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 60 results
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Best time to book a flight from Indiana to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Indiana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Indiana to New Windsor

What is the cheapest month to book a flight from Indiana to New Windsor?

Currently, March is the cheapest month in which you can book a flight from Indiana to New Windsor (average of $46). Flying from Indiana to New Windsor in January is currently the most expensive (average of $95). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Indiana to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Indiana?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Indiana.

  • How long is the flight from Indiana to New Windsor?

    Allegiant Air can get you from Indiana to New Windsor in just under 20h 45m. Your travel time can differ by up to . There are 658 mi between Indiana and New Windsor.

  • What are the most popular routes from Indiana to New Windsor?

    The most popular route from Indiana to New Windsor is Cincinnati Cinci./N. Kentucky - New Windsor Stewart. You may also consider Chicago O'Hare Intl - New Windsor Stewart or Indianapolis - New Windsor Stewart.

  • Can I find deals for flights from Indiana to Stewart that include hotel bookings?

    Yes. In addition to deals on Indiana to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indiana to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indiana to Stewart.

  • Can I find deals for business class flights from Indiana to Stewart?

    Yes. Cheapflights offers flight deals from Indiana to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Indiana to New Windsor?

    Currently, March is the cheapest month in which you can book a flight from Indiana to New Windsor (average of $46). Flying from Indiana to New Windsor in January is currently the most expensive (average of $95). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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