SWF - MDW

$159 Find Cheap Flights from Stewart Intl. to Chicago Midway Airport - Compare and Save

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 Midway departing on 10/15. 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

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Everything you should know

Cheapest round-trip
$351
Multiple Airlines
Sat 9/26Thu 10/1
SWF - MDW • 2 stops
Cheapest one-way
$165
Allegiant Air
Thu 10/15
SWF - MDW • 2 stops
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Flight Deals

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

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

Sat, Sep 26 - Thu, Oct 1
Multiple Airlines Logo
12:39 pm - 5:46 pm
SWF
-
MDW
30h 07m
2 stops
Multiple Airlines Logo
10:38 am - 10:29 am
MDW
-
SWF
22h 51m
1 stop
$351Multiple Airlines
Booking Insights

Good to know

Cheapest flight

$159
Flight from Stewart Intl. to Chicago Midway Airport

When to book flights from New Windsor to Midway

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

  • What is the cheapest flight from Stewart Intl. to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Stewart Intl. to Chicago Midway Airport was $159 for a one-way ticket and $351 for a round-trip.

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

    A passport is not required to fly from Stewart Intl. to Chicago Midway Airport.

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

    Stewart Intl. airport is called New Windsor Stewart and the only airport in Chicago Midway Airport is Chicago Midway.

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

    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 Midway Airport?

    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 Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

    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 Midway Airport with an airline and back to Stewart Intl. with another airline. Booking your flights between Stewart Intl. and MDW 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 Stewart Intl. to Chicago Midway Airport?

    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 Midway Airport 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 Midway

Information on your arrival and departure airports

Stewart Intl. (SWF)
Midway (MDW)