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$103+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — IND
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/2611:52 am
SWF
-
ORD
1 stop12h 13m
Multiple Airlines
Sat 2/2812:06 pm
ORD
-
SWF
1 stop21h 56m
Multiple Airlines
Deal found 1/26$223
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 4/3011:45 am
SWF
-
SBN
1 stop22h 14m
Allegiant Air
Sun 5/37:35 pm
SBN
-
SWF
1 stop15h 15m
Allegiant Air
Deal found 1/25$296
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/611:09 am
SWF
-
ORD
1 stop25h 13m
Multiple Airlines
Tue 2/106:07 pm
ORD
-
SWF
2 stops39h 45m
Multiple Airlines
Deal found 1/24$325
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/511:48 am
SWF
-
CVG
1 stop11h 38m
Multiple Airlines
Mon 2/99:00 am
CVG
-
SWF
1 stop9h 43m
Multiple Airlines
Deal found 1/26$330
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/511:48 am
SWF
-
MDW
1 stop9h 04m
Multiple Airlines
Sun 2/81:00 pm
MDW
-
SWF
1 stop28h 43m
Multiple Airlines
Deal found 1/25$335
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/1612:11 pm
SWF
-
MDW
2 stops9h 42m
Multiple Airlines
Wed 3/1811:19 am
MDW
-
SWF
1 stop22h 49m
Multiple Airlines
Deal found 1/24$337
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/2611:48 am
SWF
-
SBN
1 stop8h 25m
Multiple Airlines
Sun 3/18:53 pm
SBN
-
SWF
1 stop13h 20m
Multiple Airlines
Deal found 1/26$340
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/510:48 am
SWF
-
CVG
1 stop8h 02m
Multiple Airlines
Sun 2/85:07 pm
CVG
-
SWF
1 stop17h 12m
Multiple Airlines
Deal found 1/26$343
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/211:29 pm
SWF
-
SDF
2 stops25h 09m
Multiple Airlines
Sat 2/2812:00 pm
SDF
-
SWF
1 stop23h 02m
Multiple Airlines
Deal found 1/24$344
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/611:09 am
SWF
-
ORD
1 stop10h 54m
Multiple Airlines
Sun 2/83:00 pm
ORD
-
SWF
1 stop18h 19m
Multiple Airlines
Deal found 1/26$360
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 6/55:55 pm
SWF
-
CVG
1 stop5h 29m
Multiple Airlines
Sun 6/73:50 pm
CVG
-
SWF
1 stop19h 45m
Multiple Airlines
Deal found 1/25$366
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 6/1712:05 pm
SWF
-
ORD
2 stops20h 54m
Multiple Airlines
Wed 6/244:10 pm
ORD
-
SWF
1 stop15h 48m
Multiple Airlines
Deal found 1/24$380

Find flight deals from Stewart to Indiana

Keep the following information in mind while searching for Stewart to Indiana flight deals. Data was last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$269
Provider with most accurate pricing for New York (NYC)-Indianapolis flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Indianapolis flights.
Search Deals
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. 3% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Thu 2/26

11:52 am-11:05 pm

1 stop12h 13m

Chicago O'Hare Intl

Sat 2/28

12:06 pm-11:02 am

1 stop21h 56m

$223

New WindsorSouth Bend

SWF - SBN

SWFSBN

New Windsor Stewart

Thu 4/30

11:45 am-9:59 am

1 stop22h 14m

South Bend/Michiana

Sun 5/3

7:35 pm-10:50 am

1 stop15h 15m

$296

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 2/6

11:09 am-11:22 am

1 stop25h 13m

Chicago O'Hare Intl

Tue 2/10

6:07 pm-10:52 am

2 stops39h 45m

$325

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Thu 2/5

11:48 am-11:26 pm

1 stop11h 38m

Cincinnati Cinci./N. Kentucky

Mon 2/9

9:00 am-6:43 pm

1 stop9h 43m

$330

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 2/5

11:48 am-7:52 pm

1 stop9h 04m

Chicago Midway

Sun 2/8

1:00 pm-6:43 pm

1 stop28h 43m

$335

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Mon 3/16

12:11 pm-8:53 pm

2 stops9h 42m

Chicago Midway

Wed 3/18

11:19 am-11:08 am

1 stop22h 49m

$337

New WindsorSouth Bend

SWF - SBN

SWFSBN

New Windsor Stewart

Thu 2/26

11:48 am-8:13 pm

1 stop8h 25m

South Bend/Michiana

Sun 3/1

8:53 pm-10:13 am

1 stop13h 20m

$340

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Thu 2/5

10:48 am-6:50 pm

1 stop8h 02m

Cincinnati Cinci./N. Kentucky

Sun 2/8

5:07 pm-10:19 am

1 stop17h 12m

$343

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Sat 2/21

1:29 pm-2:38 pm

2 stops25h 09m

Louisville Intl

Sat 2/28

12:00 pm-11:02 am

1 stop23h 02m

$344

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 2/6

11:09 am-9:03 pm

1 stop10h 54m

Chicago O'Hare Intl

Sun 2/8

3:00 pm-10:19 am

1 stop18h 19m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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, February is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $54). 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 and Breeze Airways fly from New Windsor to Indiana in about 8h 25m. The time it takes to get you to your destination can typically vary by up to 13h 49m. The distance between New Windsor and Indiana is about 630 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The most popular route from New Windsor to Indiana is New Windsor Stewart - Indianapolis. You may also consider New Windsor Stewart - Cincinnati Cinci./N. Kentucky or New Windsor Stewart - Chicago O'Hare 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, February is the cheapest month in which you can book a flight from New Windsor to Indiana (average of $54). 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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