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Cheap flights from Chicago to New York from $81

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
10:18 am - 12:26 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
15h 08m2 stops Fort Lauderdale Dallas/Fort Worth
$214Multiple Airlines
Wed, Sep 30 - Thu, Oct 15
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 - 3:36 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 58m1 stop Fort Lauderdale
$224Multiple Airlines
Sat, Oct 17 - Thu, Oct 22
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
10:18 am - 3:36 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
30h 18m1 stop Fort Lauderdale
$225Multiple Airlines
Wed, Sep 30 - Thu, Oct 15
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
Multiple Airlines Logo
7:01 pm - 6:31 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
24h 30m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
$229Multiple Airlines
Wed, Oct 14 - Mon, Oct 19
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
Multiple Airlines Logo
10:38 am - 3:36 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 58m1 stop Fort Lauderdale
$230Multiple Airlines
Wed, Oct 14 - 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
7:01 pm - 7:31 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
13h 30m1 stop Orlando Sanford Intl
$242Multiple Airlines
Sat, Oct 17 - Mon, Oct 19
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 - 12:26 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
14h 48m2 stops Fort Lauderdale Dallas/Fort Worth
$244Multiple Airlines
Sat, Oct 17 - Thu, Oct 22
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
Multiple Airlines Logo
7:01 pm - 7:31 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
13h 30m1 stop Orlando Sanford Intl
$248Multiple Airlines
Wed, Oct 14 - Mon, Oct 19
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
12:39 pm - 12:23 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
12h 44m2 stops Raleigh-Durham Denver Intl
$249Multiple Airlines
Wed, Sep 30 - Wed, Oct 7
Multiple Airlines Logo
8:04 am - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
24h 24m1 stop Fort Lauderdale
Multiple Airlines Logo
10:38 am - 12:26 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
14h 48m2 stops Fort Lauderdale Dallas/Fort Worth
$250Multiple Airlines
Wed, Oct 14 - Thu, Oct 22

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Use the filters below to find and compare flights from Chicago to New Windsor that are best for you.

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Price

Cheapest round-trip

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 9/30

7:11 am-9:38 am

1 stop25h 27m

New Windsor Stewart

Thu 10/15

10:18 am-12:26 am

2 stops15h 08m

$214

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Sat 10/17

8:04 am-11:03 am

1 stop25h 59m

New Windsor Stewart

Thu 10/22

10:38 am-3:36 pm

1 stop29h 58m

$224

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 9/30

7:11 am-9:38 am

1 stop25h 27m

New Windsor Stewart

Thu 10/15

10:18 am-3:36 pm

1 stop30h 18m

$225

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 10/14

8:04 am-9:28 am

1 stop24h 24m

New Windsor Stewart

Mon 10/19

7:01 pm-6:31 pm

2 stops24h 30m

$229

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 10/14

8:04 am-9:28 am

1 stop24h 24m

New Windsor Stewart

Thu 10/22

10:38 am-3:36 pm

1 stop29h 58m

$230

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Sat 10/17

8:04 am-11:03 am

1 stop25h 59m

New Windsor Stewart

Mon 10/19

7:01 pm-7:31 am

1 stop13h 30m

$242

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Sat 10/17

8:04 am-11:03 am

1 stop25h 59m

New Windsor Stewart

Thu 10/22

10:38 am-12:26 am

2 stops14h 48m

$244
Quickest round-trip

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 10/14

8:04 am-9:28 am

1 stop24h 24m

New Windsor Stewart

Mon 10/19

7:01 pm-7:31 am

1 stop13h 30m

$248

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 9/30

7:11 am-9:38 am

1 stop25h 27m

New Windsor Stewart

Wed 10/7

12:39 pm-12:23 am

2 stops12h 44m

$249

ChicagoNew Windsor

ORD Chicago O'Hare Intl - SWF New Windsor Stewart

ORDSWF

Chicago O'Hare Intl

Wed 10/14

8:04 am-9:28 am

1 stop24h 24m

New Windsor Stewart

Thu 10/22

10:38 am-12:26 am

2 stops14h 48m

$250

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to New York from

How to get the cheapest flight ticket from Chicago to New Windsor

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to New Windsor?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to New Windsor from Chicago according to our data. United Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 6 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to New Windsor according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to New Windsor (CHI to SWF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to New Windsor

Best Price Found

$81

Fastest flight time

11h 10m

Direct flights

None
The best one-way flight to New Windsor from Chicago in the past 72 hours is $81. The best round-trip flight deal from Chicago to New Windsor found on momondo in the last 72 hours is $214.
The fastest flight from Chicago to New Windsor takes 11h 10m
There are no direct flights from Chicago to New Windsor. There are no popular flight routes from Chicago to New Windsor.
Search flight deals

Frequently asked questions about flying from Chicago to New Windsor

  • How far is Chicago to New Windsor Stewart by plane?

    There are 701.4 mi between Chicago and New Windsor Stewart. Typically, this will take 11h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to New Windsor Stewart Airport?

    Prices for flights from Chicago to New Windsor Stewart Airport were last updated today.

  • How old do you have to be to fly from Chicago to New Windsor Stewart Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The travel and health documents required for your trip to New Windsor Stewart Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New Windsor Stewart Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to New Windsor?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to New Windsor for you.

Can I find flights from Chicago to New Windsor with flexible booking policies on momondo?

All flight searches from Chicago to New Windsor on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to New Windsor?

momondo provides multiple filters to help you find the best flight to New Windsor from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to New Windsor right now. Can momondo alert me if prices change?

Price alerts on flights to New Windsor from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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