$272 Find cheap flights from Stewart Intl. to Chicago Midway Airport
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 6/16. 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.
Round-trip
1 adult
Economy
0 bags
Sat 6/15
Sat 6/22
Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport
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
...and more
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
In the last 7 days travelers have searched 42,211,976 times on KAYAK, and here is why:
Save 21% or moreCompare multiple travel sites with one search.
Filter your dealsChoose cabin class, free Wi-Fi and more.
Bundle and saveSave money when you bundle your flight + hotel.
Cheap flight deals from New Windsor to Midway (SWF-MDW)
These are the cheapest deals for flights from New Windsor to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Recent round-trip flight deals from New Windsor to Midway
Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Windsor to Midway.
Recent one-way flight deals from New Windsor to Midway
Only flying one-way? Below are some of the best one-way flight deals from New Windsor to Midway found on KAYAK recently.
Recent last minute flight deals from New Windsor to Midway
Leaving soon but still want a bargain? Check out these latest deals for last minute flights from New Windsor to Midway.
Recent direct flight deals from New Windsor to Midway
The latest deals for direct flights from New Windsor to Midway so you can sit back and relax without the need for a layover.
Cheap bus & train deals from New Windsor to Midway
Find recent round-trip train or bus tickets from New Windsor to Midway.
All round-trip flight deals to Midway
The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Flights from New Windsor to Midway - Travel Insights & Trends
Get data-powered insights and trends into flights from New Windsor to Midway to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest month to fly from New Windsor to Chicago Midway Airport?
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New Windsor to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from New Windsor to Chicago Midway Airport is January, where tickets cost $235 on average. On the other hand, the most expensive months are June and August, where the average cost of tickets is $500 and $452 respectively.
How far in advance should I book a flight from New Windsor to Chicago Midway Airport?
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New Windsor to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from New Windsor to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 64 days before departure.
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 New Windsor to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight from New Windsor to Chicago Midway Airport was $272 for a one-way ticket.
Do I need a passport to fly between New Windsor and Chicago Midway Airport?
A passport is not required to fly from New Windsor to Chicago Midway Airport.
Which airports will I be using when flying from New Windsor to Chicago Midway Airport?
New Windsor airport is called New Windsor Stewart and the only airport in Chicago Midway Airport is Chicago Midway.
Which aircraft models fly most regularly from New Windsor 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 New Windsor 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 New Windsor to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New Windsor 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 New Windsor 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 New Windsor 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 New Windsor with another airline. Booking your flights between New Windsor 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 New Windsor 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 New Windsor up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.
See more FAQs
Book cheap flights from Stewart Intl. to Chicago
Recent one-way flight deals
Only flying one-way? Below are some of the best one-way flight deals from New Windsor to Chicago found on KAYAK in the last 72 hours.