CHI - SWF

$109 Find Cheap Flights from Chicago to Stewart Intl. - Compare and Save

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Cheap Flights from Chicago to New Windsor (CHI-SWF)

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

Recent round-trip flight deals from Chicago to New Windsor

Thu, Dec 3 - Sun, Dec 6
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
Multiple Airlines Logo
6:49 pm - 12:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 01m1 stop Fort Lauderdale
$238Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
Multiple Airlines Logo
6:49 pm - 12:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 01m1 stop Fort Lauderdale
$243Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:04 am - 9:48 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 44m1 stop Fort Lauderdale
Multiple Airlines Logo
11:58 am - 3:30 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
28h 32m1 stop Fort Lauderdale
$247Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
Multiple Airlines Logo
6:49 pm - 12:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 01m1 stop Fort Lauderdale
$264Multiple Airlines
Sat, Oct 17 - Thu, Oct 22
Multiple Airlines Logo
8:04 am - 11:03 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
25h 59m1 stop Fort Lauderdale
Multiple Airlines Logo
10:38 am - 3:30 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 52m1 stop Fort Lauderdale
$275Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:04 am - 9:48 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 44m1 stop Fort Lauderdale
Multiple Airlines Logo
11:58 am - 9:21 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
22h 23m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$282Multiple Airlines
Wed, Sep 30 - Mon, Oct 5
Multiple Airlines Logo
7:11 am - 9:38 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
25h 27m1 stop Fort Lauderdale
Multiple Airlines Logo
7:13 pm - 6:23 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
24h 10m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
$284Multiple Airlines
Wed, Sep 30 - Sun, Oct 4
Multiple Airlines Logo
7:11 am - 9:38 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
25h 27m1 stop Fort Lauderdale
Multiple Airlines Logo
11:48 am - 2:45 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
27h 57m1 stop Fort Lauderdale
$286Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:04 am - 9:48 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 44m1 stop Fort Lauderdale
Multiple Airlines Logo
11:58 am - 9:21 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
22h 23m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$286Multiple Airlines
Sat, Oct 17 - Sun, Oct 25
Multiple Airlines Logo
8:04 am - 11:03 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
25h 59m1 stop Fort Lauderdale
Multiple Airlines Logo
11:58 am - 3:30 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
28h 32m1 stop Fort Lauderdale
$286Multiple Airlines
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Key details for Chicago to New Windsor flights

Cheapest flight

$109
Flight from Chicago O'Hare Intl Airport to New Windsor

When to book flights from Chicago to New Windsor

Are your dates flexible? Find out the best times to travel from Chicago 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 to New Windsor flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

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

    Flights from Chicago to New Windsor may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at New Windsor Stewart (SWF).

  • Do I need a passport to fly from Chicago 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 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 $238 to $1,522. That means the highest observed fare was about 6x higher than the lowest one.

  • What is the time difference between Chicago and New Windsor?

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

  • 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

Your guide to booking Chicago 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 Chicago to New Windsor

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