SWF - CHI

$100 Find Cheap Flights from Stewart Intl. 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 9/4. 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 Stewart Intl. 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 Stewart Intl. to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$344
Allegiant Air
Sun 6/21Fri 6/26
SWF - RFD • 1 stop
Cheapest one-way
$100
Multiple Airlines
Fri 9/4
SWF - ORD • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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

Sun, Jun 21 - Fri, Jun 26
Allegiant Air Logo
8:04 pm - 7:45 am
SWF
-
RFD
12h 41m
1 stop
Allegiant Air Logo
7:48 pm - 7:10 pm
RFD
-
SWF
22h 22m
1 stop
$344Allegiant Air
Sun, Jun 14 - Sat, Jun 20
Multiple Airlines Logo
9:38 am - 10:14 pm
SWF
-
ORD
13h 36m
1 stop
Multiple Airlines Logo
7:07 pm - 9:38 am
ORD
-
SWF
13h 31m
1 stop
$359Multiple Airlines
Wed, Jul 29 - Sat, Aug 1
Multiple Airlines Logo
12:05 pm - 7:39 pm
SWF
-
ORD
8h 34m
2 stops
Multiple Airlines Logo
7:07 pm - 9:38 am
ORD
-
SWF
13h 31m
1 stop
$363Multiple Airlines
Wed, Jul 22 - Sat, Jul 25
Multiple Airlines Logo
12:05 pm - 11:05 pm
SWF
-
ORD
12h 00m
2 stops
Multiple Airlines Logo
7:07 pm - 9:38 am
ORD
-
SWF
13h 31m
1 stop
$373Multiple Airlines
Wed, Jul 22 - Sat, Jul 25
Multiple Airlines Logo
12:05 pm - 11:05 pm
SWF
-
ORD
12h 00m
2 stops
Multiple Airlines Logo
7:07 pm - 9:38 am
ORD
-
SWF
13h 31m
1 stop
$379Multiple Airlines
Thu, Oct 8 - Fri, Oct 16
Multiple Airlines Logo
10:08 am - 11:58 pm
SWF
-
ORD
14h 50m
1 stop
Multiple Airlines Logo
8:45 pm - 11:39 am
ORD
-
SWF
13h 54m
2 stops
$381Multiple Airlines
Fri, May 22 - Sun, May 24
Multiple Airlines Logo
9:41 am - 11:13 pm
SWF
-
ORD
14h 32m
1 stop
Multiple Airlines Logo
5:11 pm - 8:51 am
ORD
-
SWF
14h 40m
1 stop
$382Multiple Airlines
Wed, Jul 15 - Sat, Jul 18
Multiple Airlines Logo
12:05 pm - 7:39 pm
SWF
-
ORD
8h 34m
2 stops
Multiple Airlines Logo
8:05 am - 9:38 am
ORD
-
SWF
24h 33m
1 stop
$385Multiple Airlines
Thu, Oct 8 - Mon, Oct 12
Multiple Airlines Logo
10:08 am - 11:58 pm
SWF
-
ORD
14h 50m
1 stop
Multiple Airlines Logo
8:45 pm - 11:48 am
ORD
-
SWF
14h 03m
1 stop
$389Multiple Airlines
Thu, Oct 8 - Mon, Oct 12
Allegiant Air Logo
6:15 pm - 7:12 pm
SWF
-
RFD
25h 57m
1 stop
Allegiant Air Logo
10:39 am - 6:11 pm
RFD
-
SWF
6h 32m
1 stop
$427Allegiant Air
Booking Insights

Good to know

Cheapest flight$100
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 Stewart Intl. to Chicago?

    In the last 3 days, the lowest price for a flight from Stewart Intl. to Chicago was $100 for a one-way ticket and $344 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)