HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 2, 2025.

Round-trip from

$204
(Mytrip)

One-way from

$100
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$191
From Illinois to New Windsor Stewart
Search Deals
One-way flight from Illinois to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 2, 2025.

This Mytrip deal was found by Cheapflights users on 6/30. 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.
Mon 7/285:05 amORD - SWF
1 stop13h 01mMultiple Airlines
Mon 8/47:56 pmSWF - ORD
1 stop13h 59mMultiple Airlines
Deal found 6/30$204
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Wed 8/610:24 amMLI - SWF
1 stop6h 46mAllegiant Air
Mon 8/1111:19 amSWF - MLI
1 stop7h 24mAllegiant Air
Deal found 7/1$240
This Mytrip deal was found by Cheapflights users on 7/1. 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 8/11:11 pmMDW - SWF
2 stops20h 02mAllegiant Air
Thu 8/78:03 pmSWF - MDW
2 stops18h 53mAllegiant Air
Deal found 7/1$341
This Mytrip deal was found by Cheapflights users on 7/1. 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 7/1710:47 amSTL - SWF
3 stops31h 19mMultiple Airlines
Mon 7/216:11 pmSWF - STL
2 stops23h 20mMultiple Airlines
Deal found 7/1$415
This Mytrip deal was found by Cheapflights users on 7/2. 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 7/2$425

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 July 2, 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

Mon 7/28

5:05 am-7:06 pm

1 stop13h 01m

New Windsor Stewart

Fri 8/1

7:56 pm-8:55 am

1 stop13h 59m

$214

MolineNew Windsor

MLI - SWF

MLISWF

Moline Quad-City

Wed 8/6

10:24 am-6:10 pm

1 stop6h 46m

New Windsor Stewart

Mon 8/11

11:19 am-5:43 pm

1 stop7h 24m

$240

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 8/1

1:11 pm-10:13 am

2 stops20h 02m

New Windsor Stewart

Thu 8/7

8:03 pm-1:56 pm

2 stops18h 53m

$341

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 7/17

10:47 am-7:06 pm

3 stops31h 19m

New Windsor Stewart

Mon 7/21

6:11 pm-4:31 pm

2 stops23h 20m

$415

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

$425

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

$100

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 8/1

2:46 pm-10:13 am

2 stops18h 27m

$147

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 7/31

10:47 am-7:06 pm

3 stops31h 19m

$172

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Wed 7/16

8:49 am-6:10 pm

1 stop8h 21m

$182

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 7/28

7:19 pm-11:56 am

1 stop15h 37m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 11 results
1
2

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 $222). 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 July 2, 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 July 2, 2025.
Read reviews from past customers who have flown Breeze Airways and Allegiant Air from Illinois to New Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Overall

8.1

Food

6.8

Boarding

8.4

Entertainment

6.6

Comfort

8.2

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
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Overall

8.1

Food

6.8

Boarding

8.4

Entertainment

6.6

Comfort

8.2

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
7.2
Good
709 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Overall

8.1

Food

6.8

Boarding

8.4

Entertainment

6.6

Comfort

8.2

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 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 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 $222). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to LaGuardia flights
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
Los Angeles to Newark flights
Atlanta to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
San Francisco to John F Kennedy Intl flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
San Francisco to Newark flights
Atlanta to LaGuardia flights
Dallas/Fort Worth to Newark flights
Hobby to LaGuardia flights
Atlanta to Newark flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
Hobby to Newark flights
Los Angeles to LaGuardia flights
Miami to Newark flights
Fort Lauderdale to Newark flights
Seattle to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Orlando to Newark flights
Hobby to John F Kennedy Intl flights
San Francisco to LaGuardia flights
Denver to John F Kennedy Intl flights
Seattle to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Denver to LaGuardia flights
Ontario to John F Kennedy Intl flights
George Bush Intcntl to Newark flights
Orlando to LaGuardia flights
San Diego to John F Kennedy Intl flights
Tampa to LaGuardia flights
George Bush Intcntl to LaGuardia flights
Tampa to John F Kennedy Intl flights
Denver to Newark flights
Tampa to Newark flights
Burbank to Newark flights
Sky Harbor Intl to John F Kennedy Intl flights
Charlotte to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
Austin to John F Kennedy Intl flights
West Palm Beach to John F Kennedy Intl flights
Seattle to LaGuardia flights
Austin to Newark flights
Midway to Newark flights
San Diego to Newark flights
Raleigh to LaGuardia flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.