CHI - SWF

$87 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 2/8. 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
$219
Multiple Airlines
Wed 1/28Fri 1/30
ORD - SWF • 1 stop
Cheapest one-way
$87
Multiple Airlines
Sun 2/8
MDW - SWF • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

Wed, Jan 28 - Fri, Jan 30
Multiple Airlines Logo
6:05 am - 11:33 am
ORD
-
SWF
28h 28m1 stop
Multiple Airlines Logo
11:09 am - 7:38 pm
SWF
-
ORD
9h 29m1 stop
$219Multiple Airlines
Wed, Jan 28 - Fri, Jan 30
Multiple Airlines Logo
5:32 pm - 11:33 am
ORD
-
SWF
17h 01m2 stops
Multiple Airlines Logo
11:09 am - 7:38 pm
SWF
-
ORD
9h 29m1 stop
$248Multiple Airlines
Wed, Jan 14 - Sun, Jan 18
Multiple Airlines Logo
5:57 pm - 10:19 am
ORD
-
SWF
39h 22m2 stops
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
$285Multiple Airlines
Wed, Jan 28 - Fri, Jan 30
Multiple Airlines Logo
5:32 pm - 5:59 pm
ORD
-
SWF
23h 27m3 stops
Multiple Airlines Logo
11:09 am - 11:46 pm
SWF
-
ORD
13h 37m1 stop
$307Multiple Airlines
Wed, Jan 14 - Sun, Jan 18
Multiple Airlines Logo
6:05 am - 11:33 am
ORD
-
SWF
28h 28m1 stop
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
$311Multiple Airlines
Wed, Jan 28 - Fri, Jan 30
Multiple Airlines Logo
5:32 pm - 5:59 pm
ORD
-
SWF
23h 27m3 stops
Multiple Airlines Logo
11:09 am - 11:47 am
SWF
-
ORD
25h 38m2 stops
$362Multiple Airlines
Wed, Jun 10 - Wed, Jun 17
Multiple Airlines Logo
5:32 pm - 9:38 am
ORD
-
SWF
15h 06m1 stop
Multiple Airlines Logo
12:05 pm - 5:10 pm
SWF
-
ORD
30h 05m2 stops
$391Multiple Airlines
Sat, Mar 21 - Mon, Mar 23
Multiple Airlines Logo
7:41 pm - 9:39 am
ORD
-
SWF
12h 58m1 stop
Multiple Airlines Logo
12:11 pm - 11:38 pm
SWF
-
ORD
12h 27m2 stops
$470Multiple Airlines
Sat, Jan 10 - Thu, Jan 15
Multiple Airlines Logo
8:27 pm - 11:33 am
ORD
-
SWF
14h 06m1 stop
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
$528Multiple Airlines
Sat, Jun 13 - Thu, Jun 18
Multiple Airlines Logo
5:32 pm - 9:38 am
ORD
-
SWF
15h 06m1 stop
Multiple Airlines Logo
10:28 am - 7:48 pm
SWF
-
ORD
10h 20m1 stop
$672Multiple Airlines
Booking Insights

Good to know

Cheapest flight$87
Flight from Chicago Midway 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 $87 for a one-way ticket and $219 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 airports will I be using when flying from Chicago to Stewart Intl.?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. New Windsor Stewart is the only airport in Stewart Intl.. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.

  • 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)