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Cheap flights from Chicago to New York from $88

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to New York departing on 5/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:12 pm - 11:25 am
ORD
-
SWF
21h 13m
1 stop
Multiple Airlines Logo
9:41 am - 8:03 am
SWF
-
ORD
23h 22m
1 stop
$267Multiple Airlines
Fri, May 15 - Mon, May 25
Multiple Airlines Logo
1:12 pm - 11:25 am
ORD
-
SWF
21h 13m
1 stop
Multiple Airlines Logo
5:53 pm - 11:22 am
SWF
-
ORD
42h 29m
2 stops
$280Multiple Airlines
Fri, May 15 - Mon, May 25
Multiple Airlines Logo
8:16 pm - 8:19 am
ORD
-
SWF
11h 03m
1 stop
Multiple Airlines Logo
10:09 am - 7:51 pm
SWF
-
ORD
10h 42m
1 stop
$281Multiple Airlines
Sat, Mar 7 - Thu, Mar 12
Multiple Airlines Logo
4:44 pm - 8:19 am
ORD
-
SWF
14h 35m
2 stops
Multiple Airlines Logo
10:09 am - 11:17 pm
SWF
-
ORD
14h 08m
1 stop
$326Multiple Airlines
Sat, Mar 7 - Thu, Mar 12
Multiple Airlines Logo
7:00 am - 11:25 am
ORD
-
SWF
27h 25m
2 stops
Multiple Airlines Logo
10:28 am - 7:47 pm
SWF
-
ORD
10h 19m
1 stop
$391Multiple Airlines
Fri, May 22 - Sun, May 24
Multiple Airlines Logo
6:10 pm - 9:39 am
ORD
-
SWF
14h 29m
1 stop
Multiple Airlines Logo
12:11 pm - 11:38 pm
SWF
-
ORD
12h 27m
2 stops
$433Multiple Airlines
Sat, Mar 21 - Mon, Mar 23
Multiple Airlines Logo
4:36 pm - 9:39 am
ORD
-
SWF
16h 03m
1 stop
Multiple Airlines Logo
6:25 pm - 10:36 am
SWF
-
ORD
41h 11m
2 stops
$518Multiple Airlines
Wed, Mar 25 - Sun, Mar 29
Multiple Airlines Logo
4:36 pm - 9:39 am
ORD
-
SWF
16h 03m
1 stop
Multiple Airlines Logo
11:48 am - 8:03 pm
SWF
-
ORD
9h 15m
1 stop
$524Multiple Airlines
Wed, Mar 25 - Thu, Mar 26
Multiple Airlines Logo
11:55 am - 11:31 am
ORD
-
SWF
22h 36m
2 stops
Multiple Airlines Logo
11:52 am - 11:22 am
SWF
-
ORD
24h 30m
1 stop
$526Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
8:05 am - 11:31 am
ORD
-
SWF
26h 26m
2 stops
Multiple Airlines Logo
11:48 am - 11:38 pm
SWF
-
ORD
12h 50m
1 stop
$551Multiple Airlines
Thu, Mar 19 - Thu, Mar 26

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to New Windsor that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 21, 2026.
Use the filters below to find and compare flights from Chicago to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 5/15

1:12 pm-11:25 am

1 stop21h 13m

New Windsor Stewart

Mon 5/25

9:41 am-8:03 am

1 stop23h 22m

$267

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 5/15

1:12 pm-11:25 am

1 stop21h 13m

New Windsor Stewart

Mon 5/25

5:53 pm-11:22 am

2 stops42h 29m

$280

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/7

8:16 pm-8:19 am

1 stop11h 03m

New Windsor Stewart

Thu 3/12

10:09 am-7:51 pm

1 stop10h 42m

$281

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/7

4:44 pm-8:19 am

2 stops14h 35m

New Windsor Stewart

Thu 3/12

10:09 am-11:17 pm

1 stop14h 08m

$326

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 5/22

7:00 am-11:25 am

2 stops27h 25m

New Windsor Stewart

Sun 5/24

10:28 am-7:47 pm

1 stop10h 19m

$391

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/21

6:10 pm-9:39 am

1 stop14h 29m

New Windsor Stewart

Mon 3/23

12:11 pm-11:38 pm

2 stops12h 27m

$433

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/25

4:36 pm-9:39 am

1 stop16h 03m

New Windsor Stewart

Sun 3/29

6:25 pm-10:36 am

2 stops41h 11m

$518

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/25

4:36 pm-9:39 am

1 stop16h 03m

New Windsor Stewart

Thu 3/26

11:48 am-8:03 pm

1 stop9h 15m

$524

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/26

11:55 am-11:31 am

2 stops22h 36m

New Windsor Stewart

Sun 3/1

11:52 am-11:22 am

1 stop24h 30m

$526

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 3/19

8:05 am-11:31 am

2 stops26h 26m

New Windsor Stewart

Thu 3/26

11:48 am-11:38 pm

1 stop12h 50m

$551

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 Spirit Airlines 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 41% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 7 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

Fastest flight time

11h 03m

Direct flights

None
The fastest flight from Chicago to New Windsor takes 11h 03m
There are no direct flights from Chicago to New Windsor. There are no popular flight routes from Chicago to New Windsor.
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  • 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 03m 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.

An easier way to manage your New Windsor trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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