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Stewart

$100+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
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 June 23, 2025.

Round-trip from

$209
(Mytrip)

One-way from

$100
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$240
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. 6% potential increase in price ($13 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 June 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 June 23, 2025.

This Mytrip deal was found by Cheapflights users on 6/21. 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 8/84:36 pmORD - SWF
1 stop16h 37mMultiple Airlines
Mon 8/117:56 pmSWF - ORD
1 stop13h 59mMultiple Airlines
Deal found 6/21$209
This Mytrip deal was found by Cheapflights users on 6/22. 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 7/252:54 pmMDW - SWF
2 stops18h 19mMultiple Airlines
Sun 7/277:52 pmSWF - MDW
2 stops19h 12mMultiple Airlines
Deal found 6/22$403
This Mytrip deal was found by Cheapflights users on 6/21. 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.
Mon 7/2110:47 amSTL - SWF
2 stops24h 09mMultiple Airlines
Mon 7/286:11 pmSWF - STL
2 stops23h 20mMultiple Airlines
Deal found 6/21$436

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 June 23, 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

Fri 8/8

4:36 pm-10:13 am

1 stop16h 37m

New Windsor Stewart

Mon 8/11

7:56 pm-8:55 am

1 stop13h 59m

$209

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 7/25

2:54 pm-10:13 am

2 stops18h 19m

New Windsor Stewart

Sun 7/27

7:52 pm-2:04 pm

2 stops19h 12m

$403

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Mon 7/21

10:47 am-11:56 am

2 stops24h 09m

New Windsor Stewart

Mon 7/28

6:11 pm-4:31 pm

2 stops23h 20m

$436

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/24

5:15 pm-10:12 am

1 stop15h 57m

$100

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 7/31

11:37 am-10:29 am

1 stop21h 52m

$120

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 7/10

10:47 am-7:06 pm

3 stops31h 19m

$160

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Fri 7/4

8:15 pm-12:18 pm

1 stop15h 03m

$162

MolineNew Windsor

MLI - SWF

MLISWF

Moline Quad-City

Sun 6/29

12:36 pm-7:11 pm

3 stops29h 35m

$331

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Sat 7/5

8:02 pm-7:12 pm

3 stops22h 10m

$667

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

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.

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 $218). 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 June 23, 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 June 23, 2025.
Allegiant Air
7.3
Good
715 reviews

Boarding

7.6

Entertainment

5.5

Overall

7.3

Crew

8.1

Comfort

6.8

Food

5.9

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
715 reviews
Allegiant Air
7.3
Good
715 reviews

Boarding

7.6

Entertainment

5.5

Overall

7.3

Crew

8.1

Comfort

6.8

Food

5.9

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 Chicago Midway - 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 $218). 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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