SWF - CHI

$99 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 3/8. 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 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
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Everything you should know

Cheapest round-trip
$234
Multiple Airlines
Thu 2/26Thu 3/5
SWF - ORD • 1 stop
Cheapest one-way
$99
Multiple Airlines
Sun 3/8
SWF - ORD • 1 stop
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Chicago

Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
11:52 am - 11:05 pm
SWF
-
ORD
12h 13m
1 stop
Multiple Airlines Logo
12:44 pm - 10:12 am
ORD
-
SWF
20h 28m
1 stop
$234Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
11:52 am - 9:13 pm
SWF
-
ORD
10h 21m
1 stop
Multiple Airlines Logo
7:00 am - 10:12 am
ORD
-
SWF
26h 12m
2 stops
$252Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
4:21 pm - 10:55 am
ORD
-
SWF
41h 34m
2 stops
$268Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
4:21 pm - 10:55 am
ORD
-
SWF
41h 34m
2 stops
$269Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
7:20 pm - 10:55 am
ORD
-
SWF
38h 35m
2 stops
$281Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
Multiple Airlines Logo
10:28 am - 7:48 pm
SWF
-
ORD
10h 20m
1 stop
Multiple Airlines Logo
12:41 pm - 8:49 am
ORD
-
SWF
19h 08m
1 stop
$414Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
12:22 pm - 9:13 pm
SWF
-
ORD
9h 51m
1 stop
Multiple Airlines Logo
12:44 pm - 11:31 am
ORD
-
SWF
21h 47m
2 stops
$422Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
Multiple Airlines Logo
10:28 am - 7:48 pm
SWF
-
ORD
10h 20m
1 stop
Multiple Airlines Logo
12:41 pm - 8:49 am
ORD
-
SWF
19h 08m
1 stop
$423Multiple Airlines
Wed, Feb 11 - Thu, Feb 12
Multiple Airlines Logo
5:46 pm - 10:46 am
SWF
-
ORD
18h 00m
1 stop
Multiple Airlines Logo
4:42 pm - 10:14 am
ORD
-
SWF
16h 32m
2 stops
$495Multiple Airlines
Thu, Jun 25 - Mon, Jun 29
Multiple Airlines Logo
8:04 pm - 7:45 am
SWF
-
RFD
12h 41m
1 stop
Multiple Airlines Logo
7:48 pm - 11:08 am
RFD
-
SWF
14h 20m
1 stop
$500Multiple Airlines
Booking Insights

Good to know

Cheapest flight$99
Flight from Stewart Intl. 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 $99 for a one-way ticket and $234 for a round-trip.

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

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

  • Which airports will I be using when flying from Stewart Intl. to Chicago?

    Stewart Intl. is served by only 1 airport and there are 2 airports in Chicago. You will leave Stewart Intl. 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.

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

Information on your arrival and departure airports

Stewart Intl. (SWF)