SWF - CHI

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

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$269
Typical prices: $270-$555
Multiple Airlines
Thu 11/22Mon 12/3
SWF - ORD • 1 stop
Cheapest one-way
$109
Typical prices: $191-$191
Multiple Airlines
Thu 12/6
SWF - ORD • 1 stop
Top routes
SWF - ORD
Cheapest • 35% average savings
SWF - RFD
Most popular
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Cheap Flights from New Windsor to Chicago (SWF-CHI)

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

Recent round-trip flight deals from New Windsor to Chicago

Sun, Nov 22 - Thu, Dec 3
Multiple Airlines Logo
6:48 pm - 12:38 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 50m1 stop Fort Lauderdale
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
$269Multiple Airlines
Sun, Nov 22 - Thu, Dec 3
Multiple Airlines Logo
6:48 pm - 12:38 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 50m1 stop Fort Lauderdale
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
$277Multiple Airlines
Thu, Dec 10 - Sun, Dec 13
Multiple Airlines Logo
6:49 pm - 12:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 01m1 stop Fort Lauderdale
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
$291Multiple Airlines
Sun, Nov 22 - Tue, Dec 1
Multiple Airlines Logo
6:48 pm - 12:38 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 50m1 stop Fort Lauderdale
Multiple Airlines Logo
9:21 pm - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
43h 38m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$296Multiple Airlines
Sun, Oct 25 - Sat, Oct 31
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
Multiple Airlines Logo
8:00 am - 12:08 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
27h 08m1 stop Fort Lauderdale
$297Multiple Airlines
Thu, Dec 10 - Sun, Dec 13
Multiple Airlines Logo
6:49 pm - 12:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 01m1 stop Fort Lauderdale
Multiple Airlines Logo
5:00 am - 5:59 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
11h 59m1 stop Fort Lauderdale
$298Multiple Airlines
Sun, Oct 25 - Sat, Oct 31
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
Multiple Airlines Logo
8:00 am - 12:08 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
27h 08m1 stop Fort Lauderdale
$299Multiple Airlines
Mon, Oct 19 - Wed, Oct 21
Multiple Airlines Logo
7:01 pm - 7:51 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
13h 50m1 stop Orlando Sanford Intl
Multiple Airlines Logo
8:04 am - 9:48 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 44m1 stop Fort Lauderdale
$301Multiple Airlines
Thu, Oct 8 - Wed, Oct 14
Multiple Airlines Logo
10:18 am - 3:30 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
30h 12m1 stop Fort Lauderdale
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
$302Multiple Airlines
Wed, Oct 7 - Wed, Oct 14
Multiple Airlines Logo
12:39 pm - 7:31 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
19h 52m2 stops Raleigh-Durham Orlando
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
$307Multiple Airlines
Booking Insights

Price, demand and travel trends for New Windsor to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from New Windsor to Chicago with more confidence.

What is the cheapest New Windsor to Chicago flight route?

New Windsor (SWF) to Chicago O'Hare Intl Airport (ORD) is the cheapest New Windsor to Chicago route, averaging $270 round-trip. Other New Windsor to Chicago routes average $555, based on KAYAK data over the past 12 months.

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Key details for New Windsor to Chicago flights

Cheapest flight

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

When to book flights from New Windsor to Chicago

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

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

  • Can I save money by using flexible dates for flights from New Windsor to Chicago?

    Yes. Being flexible with your travel dates can save you up to 52% on the New Windsor to Chicago route. Tuesday is the cheapest departure day at $270 round-trip on average, while Sunday is the most expensive at $555, a difference of $285. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago?

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

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

    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 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 $269 to $1,200. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from New Windsor to Chicago looking right now?

    One-way fares from New Windsor to Chicago are currently lower than usual. Average one-way flight prices are about $131, which is 32% below the typical average for this route.

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

    Chicago 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 in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

Your guide to booking New Windsor to Chicago 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 Chicago

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