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$89+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — IND
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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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 October 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Mon 11/1012:01 pmSWF - ORD
1 stop22h 46mMultiple Airlines
Sun 11/1610:52 amORD - SWF
1 stop23h 19mMultiple Airlines
Deal found 10/18$189
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/1411:01 amSWF - ORD
1 stop14h 26mMultiple Airlines
Sun 11/1610:52 amORD - SWF
1 stop23h 19mMultiple Airlines
Deal found 10/18$201
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Mon 11/1012:01 pmSWF - ORD
1 stop22h 46mMultiple Airlines
Thu 11/1310:52 amORD - SWF
1 stop22h 19mMultiple Airlines
Deal found 10/18$212
This Mytrip deal was found by Cheapflights users on 10/19. 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 11/147:05 pmSWF - SDF
1 stop14h 49mAllegiant Air
Mon 11/179:33 pmSDF - SWF
1 stop12h 53mAllegiant Air
Deal found 10/19$223
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/1311:43 amSWF - ORD
1 stop25h 43mMultiple Airlines
Sun 11/1610:52 amORD - SWF
1 stop23h 19mMultiple Airlines
Deal found 10/18$227
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/711:31 amSWF - ORD
1 stop24h 41mMultiple Airlines
Sun 11/1610:52 amORD - SWF
1 stop23h 19mMultiple Airlines
Deal found 10/18$231
This Mytrip deal was found by Cheapflights users on 10/19. 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 11/147:05 pmSWF - SDF
1 stop14h 49mMultiple Airlines
Sun 11/167:11 pmSDF - SWF
1 stop16h 00mMultiple Airlines
Deal found 10/19$232
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Mon 11/1012:01 pmSWF - ORD
1 stop22h 46mMultiple Airlines
Wed 11/126:48 amORD - SWF
1 stop27h 15mMultiple Airlines
Deal found 10/18$241
This Mytrip deal was found by Cheapflights users on 10/19. 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 10/318:06 pmSWF - SDF
1 stop13h 08mMultiple Airlines
Sun 11/27:11 pmSDF - SWF
1 stop16h 00mMultiple Airlines
Deal found 10/19$246
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/711:31 amSWF - ORD
1 stop24h 41mMultiple Airlines
Thu 11/1310:52 amORD - SWF
1 stop22h 19mMultiple Airlines
Deal found 10/18$254
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Mon 11/1012:01 pmSWF - ORD
1 stop22h 46mMultiple Airlines
Sat 11/153:26 pmORD - SWF
2 stops20h 16mMultiple Airlines
Deal found 10/18$259
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 12/1512:27 pmSWF - IND
1 stop23h 06mMultiple Airlines
Wed 12/172:13 pmIND - SWF
1 stop20h 06mMultiple Airlines
Deal found 10/19$295

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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$89
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$303
Provider with most accurate pricing for New York (NYC)-Indianapolis flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Indianapolis flights.
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From New Windsor Stewart to Indiana
Search Deals
One-way flight from New Windsor Stewart to Indiana
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 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

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Sun 11/16

10:52 am-11:11 am

1 stop23h 19m

$189

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Thu 11/13

10:52 am-10:11 am

1 stop22h 19m

$212

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 11/14

7:05 pm-9:54 am

1 stop14h 49m

Louisville Intl

Mon 11/17

9:33 pm-10:26 am

1 stop12h 53m

$223

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 11/14

7:05 pm-9:54 am

1 stop14h 49m

Louisville Intl

Sun 11/16

7:11 pm-11:11 am

1 stop16h 00m

$232

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/14

11:01 am-11:30 am

2 stops25h 29m

Chicago O'Hare Intl

Sun 11/16

3:26 pm-11:11 am

1 stop18h 45m

$238

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/31

8:06 pm-9:14 am

1 stop13h 08m

Louisville Intl

Sun 11/2

7:11 pm-11:11 am

1 stop16h 00m

$246

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/7

11:31 am-11:12 am

1 stop24h 41m

Chicago O'Hare Intl

Thu 11/13

10:52 am-10:11 am

1 stop22h 19m

$254

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Sat 11/15

3:26 pm-12:42 pm

2 stops20h 16m

$259

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 11/13

11:43 am-10:37 pm

2 stops11h 54m

Chicago O'Hare Intl

Sun 11/16

10:52 am-11:11 am

1 stop23h 19m

$272

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 1/22

11:48 am-9:23 pm

1 stop10h 35m

Chicago O'Hare Intl

Tue 1/27

5:59 pm-11:08 am

2 stops40h 09m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

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, March is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $53). Flying from New Windsor to Indiana in August is currently the most expensive (average of $97). 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 14h 49m. 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 658 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 - Louisville Intl.

  • 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, March is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $53). Flying from New Windsor to Indiana in August is currently the most expensive (average of $97). 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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