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Stewart

$101+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SWF
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
1 adult, Economy
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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 September 18, 2025.

Round-trip from

$214
(Mytrip)

One-way from

$101
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$219
From Indiana to New Windsor Stewart
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One-way flight from Indiana to New Windsor Stewart
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Highest demand for flights based on searches. 16% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 18, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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 11/65:59 pmORD - SWF
1 stop15h 42mMultiple Airlines
Mon 11/1012:01 pmSWF - ORD
1 stop9h 59mMultiple Airlines
Deal found 9/15$214
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Fri 10/36:30 amCVG - SWF
1 stop13h 01mAllegiant Air
Mon 10/611:01 amSWF - CVG
1 stop10h 36mAllegiant Air
Deal found 9/16$236
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/119:26 pmSDF - SWF
1 stop21h 14mAllegiant Air
Mon 12/155:20 pmSWF - SDF
1 stop23h 35mAllegiant Air
Deal found 9/17$242
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/1110:05 pmORD - SWF
2 stops19h 35mMultiple Airlines
Mon 12/1512:27 pmSWF - ORD
1 stop9h 33mMultiple Airlines
Deal found 9/16$250
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 12/126:00 amSDF - SWF
1 stop12h 40mMultiple Airlines
Sun 12/1411:43 amSWF - SDF
1 stop12h 02mMultiple Airlines
Deal found 9/15$253
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:58 pmSDF - SWF
1 stop15h 43mMultiple Airlines
Sun 11/26:16 pmSWF - SDF
2 stops16h 36mMultiple Airlines
Deal found 9/17$259
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:30 amCVG - SWF
1 stop13h 01mAllegiant Air
Fri 10/2411:31 amSWF - CVG
1 stop12h 08mAllegiant Air
Deal found 9/17$259
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 12/49:18 pmDAY - SWF
1 stop21h 22mAllegiant Air
Mon 12/85:44 pmSWF - DAY
1 stop17h 14mAllegiant Air
Deal found 9/15$260
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/36:30 amCVG - SWF
1 stop13h 01mMultiple Airlines
Mon 10/611:01 amSWF - CVG
2 stops31h 04mMultiple Airlines
Deal found 9/17$275
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/21:21 pmCVG - SWF
2 stops22h 00mMultiple Airlines
Mon 10/611:01 amSWF - CVG
1 stop10h 36mMultiple Airlines
Deal found 9/17$277
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Fri 10/176:30 amCVG - SWF
1 stop13h 01mAllegiant Air
Mon 10/2011:01 amSWF - CVG
1 stop10h 36mAllegiant Air
Deal found 9/15$279
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/32:38 pmSDF - SWF
1 stop19h 48mAllegiant Air
Sun 11/96:14 pmSWF - SDF
1 stop26h 29mAllegiant Air
Deal found 9/14$286

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 September 18, 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 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

Mon 11/10

12:01 pm-9:00 pm

1 stop9h 59m

$214

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 10/3

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

Mon 10/6

11:01 am-9:37 pm

1 stop10h 36m

$236

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 12/11

9:26 pm-6:40 pm

1 stop21h 14m

New Windsor Stewart

Mon 12/15

5:20 pm-4:55 pm

1 stop23h 35m

$242

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 12/12

6:00 am-6:40 pm

1 stop12h 40m

New Windsor Stewart

Sun 12/14

11:43 am-11:45 pm

1 stop12h 02m

$253

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 10/30

6:58 pm-10:41 am

1 stop15h 43m

New Windsor Stewart

Sun 11/2

6:16 pm-10:52 am

2 stops16h 36m

$259

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 10/17

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

Fri 10/24

11:31 am-11:39 pm

1 stop12h 08m

$259

DaytonNew Windsor

DAY - SWF

DAYSWF

Dayton

Thu 12/4

9:18 pm-6:40 pm

1 stop21h 22m

New Windsor Stewart

Mon 12/8

5:44 pm-10:58 am

1 stop17h 14m

$260

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 10/2

1:21 pm-11:21 am

2 stops22h 00m

New Windsor Stewart

Mon 10/6

11:01 am-9:37 pm

1 stop10h 36m

$277

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 10/17

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

Mon 10/20

11:01 am-9:37 pm

1 stop10h 36m

$279

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Mon 11/3

2:38 pm-10:26 am

1 stop19h 48m

New Windsor Stewart

Sun 11/9

6:14 pm-8:43 pm

1 stop26h 29m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, October is the cheapest month in which you can book a flight from Indiana to New Windsor (average of $109). Flying from Indiana to New Windsor in December is currently the most expensive (average of $202). 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 13h 01m. Your travel time can differ by up to . There are 581 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 Indianapolis - New Windsor Stewart or Chicago O'Hare Intl - 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, October is the cheapest month in which you can book a flight from Indiana to New Windsor (average of $109). Flying from Indiana to New Windsor in December is currently the most expensive (average of $202). 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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