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Stewart

$104+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(Mytrip)

One-way from

$104
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$248
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. 8% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This Mytrip deal was found by Cheapflights users on 3/30. 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 4/247:33 pmORD - SWF
1 stop14h 27mMultiple Airlines
Mon 4/2811:50 amSWF - ORD
1 stop22h 34mMultiple Airlines
Deal found 3/30$261

Cheapflights Fare Finder

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 March 31, 2025.
Use the filters below to find and compare flights from Illinois to New Windsor that are best for you.

Fly from

Illinois

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 4/24

7:33 pm-11:00 am

1 stop14h 27m

New Windsor Stewart

Mon 4/28

11:50 am-9:24 am

1 stop22h 34m

$261

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 5/5

8:45 am-7:49 pm

1 stop10h 04m

$104

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 5/8

10:10 am-11:00 am

1 stop23h 50m

$108

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 5/8

10:58 am-9:11 am

1 stop21h 13m

$117

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 4/21

3:22 pm-9:02 am

1 stop16h 40m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to New Windsor

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 $224). 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 March 31, 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 March 31, 2025.
Allegiant Air
7.3
Good
731 reviews

Food

5.9

Entertainment

5.5

Overall

7.3

Boarding

7.6

Crew

8.1

Comfort

6.8

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
731 reviews
Allegiant Air
7.3
Good
731 reviews

Food

5.9

Entertainment

5.5

Overall

7.3

Boarding

7.6

Crew

8.1

Comfort

6.8

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, Lambert-St Louis - New Windsor Stewart or Evansville Dress Regional - 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 $224). 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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