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$91+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Apr 21 — Apr 281
Mon 4/21
Mon 4/28
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 April 16, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$237
(Mytrip)

One-way from

$91
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$230
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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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. 3% potential increase in price ($6 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 April 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 April 16, 2025.

This Mytrip deal was found by Cheapflights users on 4/15. 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 5/911:50 amSWF - STL
1 stop22h 25mMultiple Airlines
Sun 5/1110:10 amSTL - SWF
1 stop23h 50mMultiple Airlines
Deal found 4/15$192
This Mytrip deal was found by Cheapflights users on 4/15. 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 5/18:04 pmSWF - RFD
1 stop13h 04mAllegiant Air
Sun 5/410:26 amRFD - SWF
1 stop21h 45mAllegiant Air
Deal found 4/15$241
This Mytrip deal was found by Cheapflights users on 4/15. 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 6/67:18 pmSWF - ORD
1 stop14h 32mMultiple Airlines
Mon 6/95:05 amORD - SWF
1 stop12h 23mMultiple Airlines
Deal found 4/15$248
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/2911:23 amSWF - MDW
2 stops32h 51mAllegiant Air
Sun 6/111:03 amMDW - SWF
1 stop24h 22mAllegiant Air
Deal found 4/16$355
This Mytrip deal was found by Cheapflights users on 4/15. 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 5/28:39 pmSWF - MLI
1 stop12h 04mMultiple Airlines
Sun 5/412:42 pmMLI - SWF
2 stops21h 18mMultiple Airlines
Deal found 4/15$365
This Mytrip deal was found by Cheapflights users on 4/15. 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 4/189:51 amSWF - PIA
1 stop24h 17mAllegiant Air
Tue 4/229:11 amPIA - SWF
1 stop23h 50mAllegiant Air
Deal found 4/15$623

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 April 16, 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 WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Fri 5/9

11:50 am-9:15 am

1 stop22h 25m

Lambert-St Louis

Sun 5/11

10:10 am-11:00 am

1 stop23h 50m

$192

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 5/1

8:04 pm-8:08 am

1 stop13h 04m

Chicago Greater Rockford

Sun 5/4

10:26 am-9:11 am

1 stop21h 45m

$241

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 6/6

7:18 pm-8:50 am

1 stop14h 32m

Chicago O'Hare Intl

Mon 6/9

5:05 am-6:28 pm

1 stop12h 23m

$248

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 5/29

11:23 am-7:14 pm

2 stops32h 51m

Chicago Midway

Sun 6/1

11:03 am-12:25 pm

1 stop24h 22m

$355

New WindsorMoline

SWF - MLI

SWFMLI

New Windsor Stewart

Fri 5/2

8:39 pm-7:43 am

1 stop12h 04m

Moline Quad-City

Sun 5/4

12:42 pm-11:00 am

2 stops21h 18m

$365

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 5/19

11:55 am-8:50 am

1 stop21h 55m

$91

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Fri 5/16

11:55 am-9:15 am

1 stop22h 20m

$93

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 5/1

8:04 pm-8:08 am

1 stop13h 04m

$107

New WindsorPeoria

SWF - PIA

SWFPIA

New Windsor Stewart

Fri 5/16

2:45 pm-6:18 pm

1 stop28h 33m

$138

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Wed 7/2

10:29 am-10:47 am

1 stop25h 18m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 April 16, 2025.
Allegiant Air
7.3
Good
734 reviews

Boarding

7.6

Comfort

6.8

Crew

8.1

Food

5.9

Entertainment

5.5

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
734 reviews
Allegiant Air
7.3
Good
734 reviews

Boarding

7.6

Comfort

6.8

Crew

8.1

Food

5.9

Entertainment

5.5

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 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 Greater Rockford 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.

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