CHI - SWF

$81 Find Cheap Flights from Chicago to Stewart Intl. - Compare and Save

1 adult
1 adult, Economy, 0 bags

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.

Everything you should know

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
Useful Info
Flight Deals

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

Wed, Oct 21 - Thu, Oct 29
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
10:38 am - 3:37 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 59m1 stop Fort Lauderdale
$189Multiple Airlines
Wed, Oct 21 - Thu, Oct 29
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
10:38 am - 3:37 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 59m1 stop Fort Lauderdale
$190Multiple Airlines
Sat, Oct 17 - Thu, Oct 29
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 - 3:37 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 59m1 stop Fort Lauderdale
$195Multiple Airlines
Sat, Oct 24 - Thu, Oct 29
Multiple Airlines Logo
8:04 am - 11:08 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
26h 04m1 stop Fort Lauderdale
Multiple Airlines Logo
10:38 am - 3:37 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 59m1 stop Fort Lauderdale
$199Multiple Airlines
Sat, Oct 24 - Mon, Oct 26
Multiple Airlines Logo
8:04 am - 11:08 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
26h 04m1 stop Fort Lauderdale
Multiple Airlines Logo
7:01 pm - 5:03 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
23h 02m1 stop Orlando Sanford Intl
$212Multiple Airlines
Sat, Oct 24 - Mon, Oct 26
Multiple Airlines Logo
8:04 am - 11:08 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
26h 04m1 stop Fort Lauderdale
Multiple Airlines Logo
7:01 pm - 5:03 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
23h 02m1 stop Orlando Sanford Intl
$222Multiple 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 - 3:36 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
28h 38m1 stop Fort Lauderdale
$227Multiple Airlines
Sat, Oct 24 - Mon, Oct 26
Multiple Airlines Logo
8:04 am - 11:08 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
26h 04m1 stop Fort Lauderdale
Multiple Airlines Logo
7:01 pm - 5:03 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
23h 02m1 stop Orlando Sanford Intl
$229Multiple Airlines
Thu, Nov 19 - Sun, Nov 22
Multiple Airlines Logo
8:00 am - 5:58 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
8h 58m1 stop Fort Lauderdale
Multiple Airlines Logo
6:48 pm - 12:16 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
30h 28m1 stop Fort Lauderdale
$263Multiple Airlines
Sat, Oct 24 - Fri, Oct 30
Multiple Airlines Logo
8:04 am - 11:08 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
26h 04m1 stop Fort Lauderdale
Multiple Airlines Logo
5:39 pm - 8:46 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
16h 07m1 stop Orlando Sanford Intl
$276Multiple Airlines
Useful Info

Key details for Chicago to New Windsor flights

Cheapest flight

$81
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 $189 to $1,456. That means the highest observed fare was about 8x 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.

Everything you need to know for your flight from Chicago to New Windsor

Information on your arrival and departure airports

New Windsor (SWF)