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Stewart

$98+ Cheap flights from Illinois 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Illinois to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$261
(Mytrip)

One-way from

$106
(Mytrip)
From Illinois to New Windsor Stewart
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One-way flight from Illinois to New Windsor Stewart
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Find flight deals from Illinois to Stewart

Cheapest flights from Illinois to Stewart
Explore the most affordable flight options available from Illinois to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sat 1/255:35 amORD - SWF
1 stop10h 44mMultiple Airlines
Sat 2/15:59 pmSWF - ORD
1 stop16h 40mMultiple Airlines
Deal found 1/20$232
This Mytrip deal was found by Cheapflights users on 1/20. 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 1/234:28 pmSTL - SWF
2 stops17h 52mMultiple Airlines
Sun 1/266:44 pmSWF - STL
3 stops23h 01mMultiple Airlines
Deal found 1/20$515

Find flights from Illinois to Stewart within your budget

Customize your flight search to find flights from Illinois 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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 1/25

5:35 am-5:19 pm

1 stop10h 44m

New Windsor Stewart

Sat 2/1

5:59 pm-9:39 am

1 stop16h 40m

$232

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 1/25

5:35 am-5:19 pm

1 stop10h 44m

$98

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 2/6

4:28 pm-11:25 am

2 stops17h 57m

$173

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 6/27

2:53 pm-10:11 am

2 stops18h 18m

$220

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 6/19

8:50 am-12:18 pm

3 stops26h 28m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Best time to book a flight from Illinois to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Illinois 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.

Travel insights for flights from Illinois to Stewart

Get recent, data-driven insights about flights from Illinois to Stewart including ideal travel times, pricing trends, and more.

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

Currently, October is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $109). Flying from Illinois to New Windsor in August is currently the most expensive (average of $225). 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.

What is the cheapest time of day to fly from IL to SWF?

Find hourly flight availability from Illinois to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to New Windsor as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois?

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

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

    When deciding which route to take from Illinois to New Windsor consider Chicago O'Hare Intl - New Windsor Stewart, Chicago Midway - New Windsor Stewart or Greater Peoria - New Windsor Stewart as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $109). Flying from Illinois to New Windsor in August is currently the most expensive (average of $225). 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 Illinois?

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

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