CHI - SWF

$88 Find Cheap Flights from Chicago to New Windsor

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to New Windsor departing on 5/13. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to New Windsor

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New Windsor, 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 Chicago to New Windsor, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$267
Multiple Airlines
Fri 5/15Mon 5/25
ORD - SWF • 1 stop
Cheapest one-way
$88
Multiple Airlines
Wed 5/13
ORD - SWF • 1 stop
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We hope you love your trip to New Windsor!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to New Windsor (CHI-SWF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to New Windsor 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to New Windsor

Fri, May 15 - Mon, May 25
Multiple Airlines Logo
1:12 pm - 11:25 am
ORD
-
SWF
21h 13m
1 stop
Multiple Airlines Logo
9:41 am - 8:03 am
SWF
-
ORD
23h 22m
1 stop
$267Multiple Airlines
Sat, May 16 - Mon, May 18
Multiple Airlines Logo
1:27 pm - 10:55 am
ORD
-
SWF
20h 28m
1 stop
Multiple Airlines Logo
12:15 pm - 11:10 pm
SWF
-
ORD
11h 55m
2 stops
$274Multiple Airlines
Fri, May 15 - Mon, May 25
Multiple Airlines Logo
1:12 pm - 11:25 am
ORD
-
SWF
21h 13m
1 stop
Multiple Airlines Logo
5:53 pm - 11:22 am
SWF
-
ORD
42h 29m
2 stops
$280Multiple Airlines
Sat, Mar 7 - Thu, Mar 12
Multiple Airlines Logo
8:16 pm - 8:19 am
ORD
-
SWF
11h 03m
1 stop
Multiple Airlines Logo
10:09 am - 7:51 pm
SWF
-
ORD
10h 42m
1 stop
$281Multiple Airlines
Sat, Mar 7 - Thu, Mar 12
Multiple Airlines Logo
4:44 pm - 8:19 am
ORD
-
SWF
14h 35m
2 stops
Multiple Airlines Logo
10:09 am - 11:17 pm
SWF
-
ORD
14h 08m
1 stop
$326Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
1:27 pm - 11:35 am
ORD
-
SWF
21h 08m
2 stops
Multiple Airlines Logo
11:45 am - 12:14 am
SWF
-
ORD
13h 29m
1 stop
$340Multiple Airlines
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
8:05 am - 11:31 am
ORD
-
SWF
26h 26m
2 stops
Multiple Airlines Logo
10:09 am - 7:51 pm
SWF
-
ORD
10h 42m
1 stop
$346Multiple Airlines
Fri, May 22 - Sun, May 24
Multiple Airlines Logo
7:00 am - 11:25 am
ORD
-
SWF
27h 25m
2 stops
Multiple Airlines Logo
10:28 am - 7:47 pm
SWF
-
ORD
10h 19m
1 stop
$391Multiple Airlines
Wed, Jun 3 - Thu, Jun 25
Multiple Airlines Logo
5:34 pm - 9:38 am
ORD
-
SWF
15h 04m
1 stop
Multiple Airlines Logo
8:04 pm - 2:19 pm
SWF
-
ORD
19h 15m
1 stop
$405Multiple Airlines
Tue, Jun 23 - Wed, Jul 15
Multiple Airlines Logo
5:14 pm - 11:25 am
ORD
-
SWF
17h 11m
2 stops
Multiple Airlines Logo
7:46 pm - 7:54 am
SWF
-
ORD
13h 08m
1 stop
$406Multiple Airlines
Booking Insights

Good to know

Cheapest flight$88
Flight from Chicago O'Hare Airport to Stewart Intl.

When to book flights from Chicago to New Windsor

Are your dates flexible? Find out the best times to travel from Chicago to New Windsor 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 Chicago to Stewart Intl.

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

    In the last 3 days, the lowest price for a flight from Chicago to New Windsor was $88 for a one-way ticket and $267 for a round-trip.

  • Do I need a passport to fly between Chicago and Stewart Intl.?

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

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

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

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

    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 Chicago to Stewart Intl..

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Chicago 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 Chicago to Stewart Intl.?

    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 Stewart Intl. with an airline and back to Chicago with another airline.

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

    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 Stewart Intl. from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Chicago to New Windsor

Information on your arrival and departure airports

New Windsor (SWF)