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$102+ Cheap flights from New Windsor (SWF) to Illinois

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheap flight deals from Stewart to Illinois

Keep the following information in mind while searching for Stewart to Illinois flight deals. Data was last updated junio 12, 2025.

Round-trip from

$234
(Mytrip)

One-way from

$102
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$268
From New Windsor Stewart to Illinois
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One-way flight from New Windsor Stewart to Illinois
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Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% 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 Stewart to Illinois

Cheapest flights from Stewart to Illinois
Explore the most affordable flight options available from Stewart to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 7/257:56 pmSWF - ORD
1 stop28h 57mMultiple Airlines
lun. 7/285:05 amORD - SWF
1 stop13h 01mMultiple Airlines
Deal found 6/11$234
This Mytrip deal was found by Cheapflights users on 6/10. 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.
vie. 7/257:56 pmSWF - STL
1 stop19h 43mMultiple Airlines
dom. 7/2710:47 amSTL - SWF
2 stops31h 19mMultiple Airlines
Deal found 6/10$241
This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 10/108:21 pmSWF - RFD
1 stop21h 41mAllegiant Air
lun. 10/1310:44 amRFD - SWF
1 stop22h 42mAllegiant Air
Deal found 6/11$268
This Mytrip deal was found by Cheapflights users on 6/12. 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.
mié. 7/211:50 amSWF - RFD
2 stops21h 41mMultiple Airlines
vie. 7/48:04 pmRFD - SWF
1 stop15h 14mMultiple Airlines
Deal found 6/12$293
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/2411:13 amSWF - MDW
2 stops27h 51mAllegiant Air
dom. 7/2711:37 amMDW - SWF
1 stop21h 52mAllegiant Air
Deal found 6/10$401
This Mytrip deal was found by Cheapflights users on 6/9. 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.
mar. 7/112:36 pmSWF - MLI
1 stop22h 03mMultiple Airlines
sáb. 7/51:34 pmMLI - SWF
1 stop19h 49mMultiple Airlines
Deal found 6/9$522
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 7/37:52 pmSWF - MDW
2 stops19h 12mMultiple Airlines
dom. 7/611:37 amMDW - SWF
1 stop21h 52mMultiple Airlines
Deal found 6/11$574
This Mytrip deal was found by Cheapflights users on 6/11. 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.
lun. 6/3011:21 amSWF - MLI
1 stop7h 22mAllegiant Air
mié. 7/210:29 amMLI - SWF
1 stop6h 41mAllegiant Air
Deal found 6/11$624

Cheapflights Fare Finder

Customize your flight search to find flights from Stewart to Illinois 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 junio 12, 2025.
Use the filters below to find and compare flights from New Windsor to Illinois that are best for you.

Fly from

Stewart

Fly to

Illinois

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

vie. 7/25

7:56 pm-11:53 pm

1 stop28h 57m

Chicago O'Hare Intl

lun. 7/28

5:05 am-7:06 pm

1 stop13h 01m

$234

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

vie. 7/25

7:56 pm-2:39 pm

1 stop19h 43m

Lambert-St Louis

dom. 7/27

10:47 am-7:06 pm

2 stops31h 19m

$241

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

vie. 10/10

8:21 pm-5:02 pm

1 stop21h 41m

Chicago Greater Rockford

lun. 10/13

10:44 am-10:26 am

1 stop22h 42m

$268

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

mié. 7/2

11:50 am-8:31 am

2 stops21h 41m

Chicago Greater Rockford

vie. 7/4

8:04 pm-12:18 pm

1 stop15h 14m

$293

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

jue. 7/24

11:13 am-2:04 pm

2 stops27h 51m

Chicago Midway

dom. 7/27

11:37 am-10:29 am

1 stop21h 52m

$401

New WindsorMoline

SWF - MLI

SWFMLI

New Windsor Stewart

mar. 7/1

12:36 pm-9:39 am

1 stop22h 03m

Moline Quad-City

sáb. 7/5

1:34 pm-10:23 am

1 stop19h 49m

$522

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

jue. 7/3

7:52 pm-2:04 pm

2 stops19h 12m

Chicago Midway

dom. 7/6

11:37 am-10:29 am

1 stop21h 52m

$574

New WindsorMoline

SWF - MLI

SWFMLI

New Windsor Stewart

lun. 6/30

11:21 am-5:43 pm

1 stop7h 22m

Moline Quad-City

mié. 7/2

10:29 am-6:10 pm

1 stop6h 41m

$624

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

jue. 9/11

7:12 pm-8:00 am

1 stop13h 48m

$102

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

lun. 8/11

7:56 pm-4:31 pm

1 stop21h 35m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 19 results
1
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Best time to book a flight from Stewart to Illinois

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

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $245). Flying from New Windsor to Illinois in March is currently the most expensive (average of $321). 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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated junio 12, 2025.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
725 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Stewart to Illinois. 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 from for flights from New Windsor to Illinois?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Illinois. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

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

    While some choose either New Windsor Stewart - Chicago Midway or New Windsor Stewart - Lambert-St Louis, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Illinois.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $245). Flying from New Windsor to Illinois in March is currently the most expensive (average of $321). 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

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