SWF - MDW

$145 Find Cheap Flights from Stewart Intl. to Chicago Midway Airport - Compare and Save

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1 adult, Economy, 0 bags

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Flight Deals

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

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

Recent round-trip flight deals from New Windsor to Midway

Wed, Dec 9 - Sat, Dec 19
Multiple Airlines Logo
12:39 pm - 4:06 pmSWF  New Windsor Stewart-MDW Chicago Midway
28h 27m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
$413Multiple Airlines
Sun, Dec 13 - Sat, Dec 19
Multiple Airlines Logo
6:49 pm - 4:06 pmSWF  New Windsor Stewart-MDW Chicago Midway
22h 17m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
$439Multiple Airlines
Thu, Dec 10 - Tue, Dec 15
Multiple Airlines Logo
11:06 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 36m1 stop Orlando
Multiple Airlines Logo
12:28 pm - 11:39 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 11m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$468Multiple Airlines
Thu, Dec 17 - Tue, Dec 22
Multiple Airlines Logo
12:07 pm - 12:01 amSWF  New Windsor Stewart-MDW Chicago Midway
12h 54m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 6:56 pmMDW  Chicago Midway-SWF New Windsor Stewart
21h 21m1 stop Orlando
$478Multiple Airlines
Thu, Dec 17 - Sat, Dec 19
Multiple Airlines Logo
12:07 pm - 11:17 pmSWF  New Windsor Stewart-MDW Chicago Midway
12h 10m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
$490Multiple Airlines
Thu, Nov 19 - Sat, Nov 21
Multiple Airlines Logo
6:48 pm - 11:55 amSWF  New Windsor Stewart-MDW Chicago Midway
18h 07m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:42 pm - 10:16 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 34m1 stop Orlando
$491Multiple Airlines
Thu, Dec 10 - Wed, Dec 16
Multiple Airlines Logo
11:06 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 36m1 stop Orlando
Multiple Airlines Logo
12:28 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
20h 58m2 stops Atlanta Hartsfield-Jackson Orlando
$500Multiple Airlines
Sun, Dec 13 - Tue, Dec 15
Multiple Airlines Logo
11:06 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 36m1 stop Orlando
Multiple Airlines Logo
12:28 pm - 11:39 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 11m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$503Multiple Airlines
Thu, Dec 10 - Thu, Dec 17
Multiple Airlines Logo
11:06 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 36m1 stop Orlando
Multiple Airlines Logo
8:35 pm - 11:36 amMDW  Chicago Midway-SWF New Windsor Stewart
14h 01m2 stops Orlando Charleston
$506Multiple Airlines
Wed, Nov 25 - Wed, Dec 2
Multiple Airlines Logo
11:06 am - 7:47 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 41m1 stop Orlando
Multiple Airlines Logo
12:28 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
20h 58m2 stops Atlanta Hartsfield-Jackson Orlando
$516Multiple Airlines
Useful Info

Key details for New Windsor to Chicago Midway Airport flights

Cheapest flight

$145
One-way 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

Your New Windsor to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • 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 $413 to $1,285. That means the highest observed fare was about 3x higher than the lowest one.

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

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • 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 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 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 Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking New Windsor to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

More options for your flight from New Windsor to Midway

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