MDW - SWF

$125 Find Cheap Flights from Chicago Midway Airport to Stewart Intl.

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to New Windsor departing on 11/9. 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

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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Flight Deals

Cheap Flights from Midway to New Windsor (MDW-SWF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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 Midway to New Windsor

Wed, Nov 26 - Sun, Nov 30
Multiple Airlines Logo
5:30 pm - 11:03 amMDW-SWF
16h 33m1 stop
Multiple Airlines Logo
8:41 pm - 4:52 pmSWF-MDW
21h 11m1 stop
$682Multiple Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
Multiple Airlines Logo
5:30 pm - 11:03 amMDW-SWF
16h 33m1 stop
Multiple Airlines Logo
8:41 pm - 2:31 pmSWF-MDW
18h 50m2 stops
$762Multiple Airlines
Find Deal
Fri, Nov 21 - Fri, Nov 28
Multiple Airlines Logo
8:41 pm - 11:03 amMDW-SWF
37h 22m2 stops
Multiple Airlines Logo
7:28 pm - 9:32 amSWF-MDW
15h 04m1 stop
$817Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$682
Multiple Airlines
Wed 11/26Sun 11/30
MDW - SWF • 1 stop
Cheapest one-way
$125
Allegiant Air
Sun 11/9
MDW - SWF • 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 New Windsor!
Booking Insights

Good to know

Cheapest flight$125
Flight from Chicago Midway Airport to Stewart Intl.

When to book flights from Midway to New Windsor

Are your dates flexible? Find out the best times to travel from Midway 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 Chicago Midway Airport to Stewart Intl. flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to New Windsor was $125 for a one-way ticket and $682 for a round-trip.

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

    No

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SWF can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway to New Windsor

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
New Windsor (SWF)

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