Which airports can I use when flying from New Windsor to Chicago Midway Airport?

Flights from New Windsor to Chicago Midway Airport usually depart from New Windsor Stewart (SWF) and arrive at Chicago Midway (MDW).

What popular places can I visit in Chicago Midway Airport?

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Do I need a passport to fly from New Windsor to Chicago Midway Airport?

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 New Windsor to Chicago Midway Airport 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 $466 to $1,274. That means the highest observed fare was about 3x higher than the lowest one.

What is the time difference between New Windsor and Chicago Midway Airport?

Chicago Midway Airport is 1 hour behind New Windsor (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

What car rental options are available at Chicago Midway Airport (MDW)?

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include: • Hertz • Dollar • Budget • Alamo • Rent-A-Wreck

Cheap Flights from New Windsor to Chicago Midway | KAYAK

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 Chicago Midway Airport!

Flight Deals

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

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

Round-trip

One-way

Recent round-trip flight deals from New Windsor to Midway

Sun, Dec 6 - Wed, Dec 9

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

9:23 pm - 5:59 pmMDW Chicago Midway-SWF New Windsor Stewart

19h 36m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$466Multiple Airlines

Thu, Dec 17 - Sun, Dec 20

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

8:07 pm - 11:36 amMDW Chicago Midway-SWF New Windsor Stewart

14h 29m2 stops Orlando Charleston

$617Multiple Airlines

Mon, Dec 21 - Sat, Dec 26

5:46 pm - 8:52 amSWF New Windsor Stewart-MDW Chicago Midway

16h 06m1 stop Punta Gorda

8:07 pm - 10:26 amMDW Chicago Midway-SWF New Windsor Stewart

13h 19m1 stop Orlando

$633Multiple Airlines

Sun, Dec 6 - Sat, Dec 12

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

9:41 pm - 5:59 pmMDW Chicago Midway-SWF New Windsor Stewart

19h 18m2 stops Dallas/Fort Worth Fort Lauderdale

$635Multiple Airlines

Thu, Dec 17 - Sun, Dec 20

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

8:07 pm - 11:36 amMDW Chicago Midway-SWF New Windsor Stewart

14h 29m2 stops Orlando Charleston

$766Multiple Airlines

Thu, Dec 17 - Sun, Dec 20

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

8:07 pm - 11:36 amMDW Chicago Midway-SWF New Windsor Stewart

14h 29m2 stops Orlando Charleston

$771Multiple Airlines

Thu, Dec 24 - Tue, Dec 29

11:06 am - 7:02 pmSWF New Windsor Stewart-MDW Chicago Midway

8h 56m1 stop Orlando

9:23 pm - 11:39 amMDW Chicago Midway-SWF New Windsor Stewart

13h 16m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham

$788Multiple Airlines

Wed, Nov 25 - Sun, Nov 29

11:06 am - 7:47 pmSWF New Windsor Stewart-MDW Chicago Midway

9h 41m1 stop Orlando

8:42 pm - 11:36 amMDW Chicago Midway-SWF New Windsor Stewart

13h 54m2 stops Orlando Charleston

$823Multiple Airlines

Wed, Nov 25 - Sat, Nov 28

9:29 am - 7:47 pmSWF New Windsor Stewart-MDW Chicago Midway

11h 18m1 stop Orlando Sanford Intl

8:42 pm - 8:39 amMDW Chicago Midway-SWF New Windsor Stewart

10h 57m1 stop Orlando

$874Multiple Airlines

Useful Info

Cheapest flight	$141

Flight from New Windsor 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.

Which airports can I use when flying from New Windsor to Chicago Midway Airport?
Flights from New Windsor to Chicago Midway Airport usually depart from New Windsor Stewart (SWF) and arrive at Chicago Midway (MDW).
What popular places can I visit in Chicago Midway Airport?
Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.
Do I need a passport to fly from New Windsor to Chicago Midway Airport?
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 New Windsor to Chicago Midway Airport 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 $466 to $1,274. That means the highest observed fare was about 3x higher than the lowest one.
What is the time difference between New Windsor and Chicago Midway Airport?
Chicago Midway Airport is 1 hour behind New Windsor (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.
What car rental options are available at Chicago Midway Airport (MDW)?
Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
- DoubleTree by Hilton Chicago Midway Airport
- Holiday Inn Chicago - Midway Airport S by IHG
- Skylark Motel

More options for your flight from New Windsor to Midway

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago

Hotels in Chicago

Vacations in Chicago

SWF - MDW

$141 Find Cheap Flights from Stewart Intl. to Chicago Midway Airport - Compare and Save

Everything you should know

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

Recent round-trip flight deals from New Windsor to Midway

Recent one-way flight deals from New Windsor to Midway

Key details for New Windsor to Chicago Midway Airport flights

Cheapest flight

When to book flights from New Windsor to Midway

Your New Windsor to Chicago Midway Airport flight questions, answered

Your guide to booking New Windsor to Chicago Midway Airport flights

More options for your flight from New Windsor to Midway

Complete your trip to Chicago with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to Midway

Find direct flights to and from New Windsor and Midway

Flights from domestic origins to Midway

Choose which airport to fly into in New Windsor

Flights to other popular destinations

Find deals for your return flight