SWF - CHI

$88 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 1/9. 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
$172
Multiple Airlines
Fri 1/23Sun 1/25
SWF - ORD • 1 stop
Cheapest one-way
$88
Multiple Airlines
Fri 1/9
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

Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
11:09 am - 7:38 pm
SWF
-
ORD
9h 29m1 stop
Multiple Airlines Logo
5:32 pm - 10:19 am
ORD
-
SWF
15h 47m1 stop
$172Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
Multiple Airlines Logo
8:43 pm - 10:19 am
ORD
-
SWF
12h 36m1 stop
$325Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
Multiple Airlines Logo
8:43 pm - 10:19 am
ORD
-
SWF
12h 36m1 stop
$326Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
Multiple Airlines Logo
8:43 pm - 10:19 am
ORD
-
SWF
12h 36m1 stop
$334Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
12:13 pm - 7:41 pm
SWF
-
ORD
8h 28m1 stop
Multiple Airlines Logo
8:43 pm - 10:19 am
ORD
-
SWF
12h 36m1 stop
$346Multiple Airlines
Mon, Dec 22 - Sun, Jan 4
Multiple Airlines Logo
8:25 pm - 3:42 pm
SWF
-
ORD
20h 17m1 stop
Multiple Airlines Logo
8:09 pm - 11:44 am
ORD
-
SWF
14h 35m2 stops
$432Multiple Airlines
Sat, Dec 20 - Wed, Dec 24
Multiple Airlines Logo
7:50 pm - 9:23 am
SWF
-
MDW
14h 33m1 stop
Multiple Airlines Logo
3:10 pm - 11:03 am
MDW
-
SWF
18h 53m1 stop
$446Multiple Airlines
Mon, Dec 22 - Sun, Jan 4
Multiple Airlines Logo
8:25 pm - 3:42 pm
SWF
-
ORD
20h 17m1 stop
Multiple Airlines Logo
4:44 pm - 10:47 am
ORD
-
SWF
17h 03m1 stop
$449Multiple Airlines
Mon, Dec 22 - Tue, Dec 30
Allegiant Air Logo
7:10 pm - 7:04 pm
SWF
-
RFD
24h 54m1 stop
Allegiant Air Logo
7:54 pm - 4:44 pm
RFD
-
SWF
19h 50m1 stop
$508Allegiant Air
Wed, Dec 24 - Sun, Dec 28
Allegiant Air Logo
10:40 am - 5:56 pm
SWF
-
RFD
8h 16m1 stop
Allegiant Air Logo
7:24 pm - 9:30 am
RFD
-
SWF
13h 06m1 stop
$779Allegiant Air
Booking Insights

Good to know

Cheapest flight$88
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 $85 for a one-way ticket and $172 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)