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$90+ Cheap flights from New Windsor (SWF) to Indiana

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — IND
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Stewart to Indiana

Keep the following information in mind while searching for Stewart to Indiana flight deals. Data was last updated August 20, 2025.

Round-trip from

$209
(Mytrip)

One-way from

$90
(Mytrip)

Popular in

May

Cheapest in

February

Average price

$249
From New Windsor Stewart to Indiana
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One-way flight from New Windsor Stewart to Indiana
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Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Stewart to Indiana

Cheapest flights from Stewart to Indiana
Explore the most affordable flight options available from Stewart to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 10/3111:31 amSWF - ORD
1 stop7h 53mMultiple Airlines
Sun 11/27:29 pmORD - SWF
1 stop14h 42mMultiple Airlines
Deal found 8/19$209
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 10/312:11 pmSWF - CVG
1 stop11h 28mAllegiant Air
Sun 10/55:32 pmCVG - SWF
1 stop16h 39mAllegiant Air
Deal found 8/19$216
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 10/318:06 pmSWF - SDF
1 stop13h 08mAllegiant Air
Mon 11/32:38 pmSDF - SWF
1 stop19h 48mAllegiant Air
Deal found 8/18$219
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 10/312:11 pmSWF - ORD
1 stop11h 37mMultiple Airlines
Sun 10/54:45 pmORD - SWF
1 stop16h 26mMultiple Airlines
Deal found 8/19$224
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Fri 10/312:11 pmSWF - SDF
1 stop9h 53mMultiple Airlines
Sun 10/56:58 pmSDF - SWF
1 stop15h 13mMultiple Airlines
Deal found 8/19$228
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Mon 9/811:53 amSWF - IND
1 stop10h 19mAllegiant Air
Thu 9/118:30 amIND - SWF
1 stop9h 52mAllegiant Air
Deal found 8/19$231
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 10/1711:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Sun 10/197:29 pmORD - SWF
1 stop13h 42mMultiple Airlines
Deal found 8/19$232
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Fri 10/1711:31 amSWF - CVG
1 stop12h 08mAllegiant Air
Sun 10/195:32 pmCVG - SWF
1 stop16h 39mAllegiant Air
Deal found 8/18$236
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 9/1211:53 amSWF - IND
1 stop10h 19mAllegiant Air
Sun 9/148:30 amIND - SWF
1 stop9h 52mAllegiant Air
Deal found 8/19$237
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/306:16 pmSWF - SDF
1 stop26h 34mAllegiant Air
Mon 11/32:38 pmSDF - SWF
1 stop19h 48mAllegiant Air
Deal found 8/18$237
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 10/248:06 pmSWF - SDF
1 stop13h 08mAllegiant Air
Mon 10/272:38 pmSDF - SWF
1 stop19h 48mAllegiant Air
Deal found 8/17$238
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 10/248:06 pmSWF - CVG
1 stop22h 36mMultiple Airlines
Mon 10/276:00 amCVG - SWF
1 stop8h 11mMultiple Airlines
Deal found 8/18$243

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Indiana 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 August 20, 2025.
Use the filters below to find and compare flights from New Windsor to Indiana that are best for you.

Fly from

Stewart

Fly to

Indiana

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/31

11:31 am-1:03 am

1 stop14h 32m

Chicago O'Hare Intl

Sun 11/2

7:29 pm-11:11 am

1 stop14h 42m

$209

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 10/3

12:11 pm-11:39 pm

1 stop11h 28m

Cincinnati Cinci./N. Kentucky

Sun 10/5

5:32 pm-10:11 am

1 stop16h 39m

$216

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/31

8:06 pm-9:14 am

1 stop13h 08m

Louisville Intl

Mon 11/3

2:38 pm-10:26 am

1 stop19h 48m

$219

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/14

11:01 am-11:42 pm

1 stop13h 41m

Chicago O'Hare Intl

Sun 11/16

5:59 pm-11:11 am

1 stop16h 12m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/24

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Sun 10/26

7:29 pm-2:11 pm

1 stop17h 42m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/3

12:11 pm-10:48 pm

1 stop11h 37m

Chicago O'Hare Intl

Sun 10/5

4:45 pm-10:11 am

1 stop16h 26m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/6

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Thu 10/9

7:29 pm-10:51 am

1 stop14h 22m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/17

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Sun 10/19

7:29 pm-10:11 am

1 stop13h 42m

$224

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/3

12:11 pm-10:04 pm

1 stop9h 53m

Louisville Intl

Sun 10/5

6:58 pm-10:11 am

1 stop15h 13m

$228

New WindsorIndianapolis

SWF - IND

SWFIND

New Windsor Stewart

Mon 9/8

11:53 am-10:12 pm

1 stop10h 19m

Indianapolis

Thu 9/11

8:30 am-6:22 pm

1 stop9h 52m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

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

Have a flexible travel schedule? Discover the best time to fly to Indiana from Stewart 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 New Windsor to Indiana

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $295). Flying from New Windsor to Indiana in March is currently the most expensive (average of $360). 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 Stewart to Indiana. 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 from for flights from New Windsor to Indiana?

    For a flight from New Windsor to Indiana, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

    Airlines like Allegiant Air fly from New Windsor to Indiana in about 11h 28m. The time it takes to get you to your destination can typically vary by up to . The distance between New Windsor and Indiana is about 581 mi.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Indiana 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 New Windsor to Indiana?

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $295). Flying from New Windsor to Indiana in March is currently the most expensive (average of $360). 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

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