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

Sign in

English

Search for a country or language

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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!

Flight Deals

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

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Recent round-trip flight deals from Midway to New Windsor

Thu, Dec 3 - Mon, Dec 7

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$416Multiple Airlines

Thu, Dec 3 - Mon, Dec 7

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$419Multiple Airlines

Thu, Dec 3 - Mon, Dec 7

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$420Multiple Airlines

Thu, Dec 10 - Mon, Dec 14

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$424Multiple Airlines

Thu, Dec 10 - Mon, Dec 14

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$425Multiple Airlines

Thu, Dec 10 - Mon, Dec 14

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$427Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

11:06 am - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

10h 36m1 stop Orlando

$433Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

11:06 am - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

10h 36m1 stop Orlando

$436Multiple Airlines

Thu, Dec 3 - Mon, Dec 7

6:10 pm - 8:52 amMDW Chicago Midway-SWF New Windsor Stewart

13h 42m1 stop Punta Gorda

12:16 pm - 8:42 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 26m2 stops Charleston Orlando

$437Multiple Airlines

Fri, Nov 20 - Mon, Nov 23

2:28 pm - 11:39 amMDW Chicago Midway-SWF New Windsor Stewart

20h 11m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham

6:32 pm - 8:42 amSWF New Windsor Stewart-MDW Chicago Midway

15h 10m1 stop Punta Gorda

$445Multiple Airlines

Useful Info

Cheapest flight	$128

One-way flight from Chicago Midway Airport to New Windsor

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.

Do I need a passport to fly from Chicago Midway Airport to New Windsor?
No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.
Have flight prices from Chicago Midway Airport to New Windsor changed much recently?
Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $416 to $1,740. That means the highest observed fare was about 4x higher than the lowest one.
What car rental options are available at New Windsor Stewart Airport (SWF)?
New Windsor Stewart Airport (SWF) hosts 5 major car rental companies, with daily rates starting from around $30 for economy cars. Top options include:

• Budget
• Avis
• Alamo
• Empire Rent A Car
• Enterprise Rent-A-Car
Which airports can I use when flying from Chicago Midway Airport to New Windsor?
Flights from Chicago Midway Airport to New Windsor usually depart from Chicago Midway (MDW) and arrive at New Windsor Stewart (SWF).
What is the time difference between Chicago Midway Airport and New Windsor?
New Windsor is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

If you're arriving late at night and need somewhere to stay, check out these hotels close to New Windsor Stewart Airport.

• Homewood Suites by Hilton Newburgh-Stewart Airport

More options for your flight from Midway to New Windsor

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Origins

Other destinations

Return flight

Complete your trip to New Windsor with a hotel stay or car rental

Car rentals in New Windsor

Hotels in New Windsor