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Stewart

$105+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Illinois to Stewart

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(Mytrip)

One-way from

$105
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$185
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Illinois to New Windsor Stewart
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One-way flight from Illinois to New Windsor Stewart
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Highest demand for flights based on searches. 9% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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 5/86:34 pmORD - SWF
1 stop15h 26mMultiple Airlines
Mon 5/1211:50 amSWF - ORD
1 stop9h 50mMultiple Airlines
Deal found 2/20$229
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 3/69:20 amSTL - SWF
3 stops23h 00mMultiple Airlines
Mon 3/1012:00 pmSWF - STL
3 stops29h 42mMultiple Airlines
Deal found 2/19$467

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 February 20, 2025.

Fly from

Illinois

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 5/8

6:34 pm-11:00 am

1 stop15h 26m

New Windsor Stewart

Mon 5/12

11:50 am-8:40 pm

1 stop9h 50m

$229

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 3/6

9:20 am-9:20 am

3 stops23h 00m

New Windsor Stewart

Mon 3/10

12:00 pm-4:42 pm

3 stops29h 42m

$467

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 3/3

7:13 pm-11:49 am

1 stop15h 36m

$105

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Tue 4/1

6:36 pm-10:01 am

1 stop14h 25m

$118

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Sun 4/13

6:11 pm-11:00 am

1 stop15h 49m

$118

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 $226). 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 February 20, 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.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated February 20, 2025.
Allegiant Air
7.3
Good
765 reviews

Boarding

7.6

Entertainment

5.5

Comfort

6.8

Crew

8.1

Food

5.9

Overall

7.3

Reviews

1 / 20

10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Allegiant Air
7.3
Good
765 reviews
Allegiant Air
7.3
Good
765 reviews

Boarding

7.6

Entertainment

5.5

Comfort

6.8

Crew

8.1

Food

5.9

Overall

7.3

Reviews

1 / 20

10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

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 $226). 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?

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