HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$100+ Cheap flights from Chicago (CHI) 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.
CHI — SWF
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago 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 Chicago to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 3, 2025.

Round-trip from

$214
(Mytrip)

One-way from

$100
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$191
From Chicago (CHI) to New Windsor Stewart
Search Deals
One-way flight from Chicago (CHI) 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 Chicago to Stewart

Cheapest flights from Chicago to Stewart
Explore the most affordable flight options available from Chicago to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 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
Fri 8/17:56 pmSWF - ORD
1 stop13h 59mMultiple Airlines
Deal found 6/30$214
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 7/2. 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 Chicago 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 3, 2025.
Use the filters below to find and compare flights from Chicago to New Windsor that are best for you.

Fly from

Chicago

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

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

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Best time to book a flight from Chicago to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $109). Flying from Chicago 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.

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 3, 2025.
Peruse reviews from past customers who have flown with Allegiant Air from Chicago to New Windsor to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.3
Good
708 reviews

Comfort

6.8

Food

5.9

Overall

7.3

Crew

8.1

Entertainment

5.5

Boarding

7.6

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
708 reviews
Allegiant Air
7.3
Good
708 reviews

Comfort

6.8

Food

5.9

Overall

7.3

Crew

8.1

Entertainment

5.5

Boarding

7.6

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 Chicago 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 Chicago?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to New Windsor from Chicago. Booking flights from Chicago to Stewart (SWF) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • What is the cheapest airline to fly from Chicago to New Windsor round-trip?

    Cheapflights users have booked flights from Chicago to New Windsor round-trip from $341.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $109). Flying from Chicago 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 Chicago?

Book flights to Chicago 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 Chicago to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
St. Louis to LaGuardia flights
St. Louis to Newark flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Albany flights
O'Hare Intl to Stewart flights
O'Hare Intl to Rochester flights
Midway to Buffalo flights
O'Hare Intl to White Plains flights
Moline to Newark flights
Moline to LaGuardia flights
Moline to John F Kennedy Intl flights
Midway to Syracuse flights
Midway to Albany flights
St. Louis to Syracuse flights
St. Louis to Buffalo flights
O'Hare Intl to Ithaca flights
O'Hare Intl to Islip flights
Midway to Rochester flights
Peoria to LaGuardia flights
Moline to Rochester flights
Evansville to John F Kennedy Intl flights
Midway to White Plains flights
St. Louis to Albany flights
Bloomington to LaGuardia flights
St. Louis to White Plains flights
St. Louis to Rochester flights
Peoria to Newark flights
Moline to White Plains flights
Evansville to Newark flights
O'Hare Intl to Rutland flights
Evansville to LaGuardia flights
Moline to Syracuse flights
Bloomington to John F Kennedy Intl flights
Peoria to John F Kennedy Intl flights
Peoria to Buffalo flights
Peoria to Rochester flights
O'Hare Intl to Elmira flights
Midway to Stewart flights
O'Hare Intl to Binghamton flights
Bloomington to Newark flights
Midway to Binghamton flights
Peoria to Albany 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.