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SWF - CHI

$141 Find cheap flights from New Windsor to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Chicago departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 6/21
Fri 6/28

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

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Cheap flight deals from New Windsor to Chicago (SWF-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:46 pm - 11:29 pmSWF-ORD
35h 43m2 stops
11:01 am - 9:45 amORD-SWF
21h 44m2 stops
$246
Find Deal
Mon, Jun 3 - Wed, Jun 12
6:43 pm - 8:24 pmSWF-ORD
26h 41m1 stop
11:01 am - 9:45 amORD-SWF
21h 44m2 stops
$252
Find Deal
Mon, Jun 3 - Wed, Jun 12
6:43 pm - 8:24 pmSWF-ORD
26h 41m1 stop
6:16 pm - 9:45 amORD-SWF
14h 29m1 stop
$402
Find Deal
Mon, Jun 3 - Wed, Jun 12
6:55 pm - 8:24 amSWF-ORD
38h 29m3 stops
7:18 am - 6:05 pmORD-SWF
9h 47m1 stop
$443
Find Deal
Fri, Jun 21 - Fri, Jun 28
11:36 am - 11:21 pmSWF-ORD
12h 45m1 stop
7:18 am - 5:31 pmORD-SWF
9h 13m1 stop
$481
Find Deal
Sat, Jun 15 - Sat, Jun 22
6:55 pm - 11:21 pmSWF-ORD
29h 26m3 stops
9:10 pm - 5:31 pmORD-SWF
19h 21m2 stops
$499
Find Deal
Fri, Jun 21 - Fri, Jun 28
6:55 pm - 8:24 amSWF-ORD
38h 29m3 stops
6:40 pm - 5:31 pmORD-SWF
21h 51m3 stops
$555
Find Deal
Fri, Jun 21 - Fri, Jun 28
11:36 am - 11:21 pmSWF-ORD
12h 45m1 stop
8:39 pm - 5:27 pmORD-SWF
19h 48m2 stops
$572
Find Deal
Sat, Jun 15 - Sat, Jun 22
11:36 am - 11:21 pmSWF-ORD
12h 45m1 stop
11:08 am - 5:27 pmORD-SWF
29h 19m3 stops
$659
Find Deal
Sat, Jun 15 - Sat, Jun 22
7:46 pm - 6:11 pmSWF-RFD
23h 25m1 stop
11:47 am - 9:58 amRFD-SWF
21h 11m1 stop
$686Allegiant Air
Find Deal
Sun, May 26 - Wed, May 29

Flights from New Windsor to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from New Windsor to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from New Windsor to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New Windsor to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from New Windsor to Chicago is February, where tickets cost $195 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $348 and $308 respectively.

How far in advance should I book a flight from New Windsor to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New Windsor to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from New Windsor to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 77 days before departure.

Good to know

Cheapest flight

$141
Flight from New Windsor to Chicago O'Hare Airport

When to book flights from New Windsor to Chicago

Are your dates flexible? Find out the best times to travel from New Windsor to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Stewart Intl. to Chicago

  • What is the cheapest flight from New Windsor to Chicago?

    In the last 3 days, the lowest price for a flight from New Windsor to Chicago was $141 for a one-way ticket and $246 for a round-trip.

  • Do I need a passport to fly between New Windsor and Chicago?

    No, a passport isn't needed to fly from New Windsor to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from New Windsor to Chicago?

    New Windsor is served by only 1 airport and there are 2 airports in Chicago. You will leave New Windsor from New Windsor Stewart and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Stewart Intl. to Chicago?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Stewart Intl. to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stewart Intl. to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Stewart Intl. is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stewart Intl. to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Stewart Intl. with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Stewart Intl. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Stewart Intl. to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New Windsor to Chicago found on KAYAK in the last 72 hours.
6/3Mon
1 stop
10h 07mSWF-ORD
$141
7/24Wed
2 stops
10h 55mSWF-ORD
$154
7/7Sun
1 stop
26h 05mSWF-ORD
$159
7/26Fri
1 stop
7h 15mSWF-ORD
$161
7/17Wed
1 stopAllegiant Air
8h 11mSWF-RFD
$164
5/31Fri
1 stop
13h 32mSWF-ORD
$167
7/5Fri
1 stop
7h 13mSWF-ORD
$168
7/19Fri
1 stop
7h 15mSWF-ORD
$169
7/5Fri
1 stop
7h 13mSWF-ORD
$170
6/9Sun
2 stopsAllegiant Air
18h 49mSWF-MDW
$205

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Last minute flights from New Windsor to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from New Windsor to Chicago that are departing in the next 10 days.
5/26Sun
multi-stopAllegiant Air
23h 25mSWF-RFD
5/29Wed
multi-stopAllegiant Air
21h 11mRFD-SWF
$686

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New Windsor - Chicago Flights

Departure:

Stewart Intl. (undefined)United States

Return flight deals:

Chicago - Stewart Intl.

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