MDW - SWF

$149 Find Cheap Flights from Chicago Midway Airport to Stewart Intl. - Compare and Save

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1 adult, Economy, 0 bags

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Flight Deals

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

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

Recent round-trip flight deals from Midway to New Windsor

Sun, Dec 6 - Sun, Dec 13
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
6:49 pm - 11:33 amSWF  New Windsor Stewart-MDW Chicago Midway
41h 44m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$341Multiple Airlines
Sun, Dec 6 - Sun, Dec 13
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
6:49 pm - 11:33 amSWF  New Windsor Stewart-MDW Chicago Midway
41h 44m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$353Multiple Airlines
Sat, Feb 13 - Wed, Feb 17
Multiple Airlines Logo
8:47 pm - 10:16 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 29m1 stop Orlando
Multiple Airlines Logo
12:29 pm - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
32h 13m2 stops Raleigh-Durham Orlando
$416Multiple Airlines
Thu, Dec 3 - Sat, Dec 19
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:29 pm - 12:01 amSWF  New Windsor Stewart-MDW Chicago Midway
12h 32m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
$451Multiple Airlines
Sat, Dec 19 - Mon, Dec 21
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
Multiple Airlines Logo
5:46 pm - 8:52 amSWF  New Windsor Stewart-MDW Chicago Midway
16h 06m1 stop Punta Gorda
$510Multiple Airlines
Sat, Dec 19 - Mon, Dec 21
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
Multiple Airlines Logo
5:46 pm - 8:52 amSWF  New Windsor Stewart-MDW Chicago Midway
16h 06m1 stop Punta Gorda
$514Multiple Airlines
Sat, Dec 19 - Mon, Dec 21
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
Multiple Airlines Logo
5:46 pm - 8:52 amSWF  New Windsor Stewart-MDW Chicago Midway
16h 06m1 stop Punta Gorda
$515Multiple Airlines
Sat, Dec 19 - Mon, Dec 21
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
Multiple Airlines Logo
5:46 pm - 8:52 amSWF  New Windsor Stewart-MDW Chicago Midway
16h 06m1 stop Punta Gorda
$527Multiple Airlines
Thu, Feb 25 - Sun, Feb 28
Multiple Airlines Logo
8:47 pm - 10:57 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 10m2 stops Orlando Charleston
Multiple Airlines Logo
10:56 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 46m1 stop Orlando
$547Multiple Airlines
Sat, Dec 19 - Mon, Dec 21
Multiple Airlines Logo
8:35 pm - 10:26 amMDW  Chicago Midway-SWF New Windsor Stewart
12h 51m1 stop Orlando
Multiple Airlines Logo
5:46 pm - 8:52 amSWF  New Windsor Stewart-MDW Chicago Midway
16h 06m1 stop Punta Gorda
$549Multiple Airlines
Useful Info

Key details for Chicago Midway Airport to New Windsor flights

Cheapest flight

$149
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

Your Chicago Midway Airport to New Windsor 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 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 $341 to $1,562. That means the highest observed fare was about 5x 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 averaging $89 for economy cars. Top options include:

    • Budget
    • Avis
    • Alamo
    • Enterprise Rent-A-Car
    • Empire 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.

Your guide to booking Chicago Midway Airport to New Windsor flights

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

More options for your flight from Midway to New Windsor

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