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.

$97 Cheap Flights from Chicago to New Windsor in 2026

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0 bags

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Find the cheapest flights from Chicago to New York

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:43 pm - 10:19 am

ORD

SWF

12h 36m

1 stop

11:09 am - 11:22 am

SWF

ORD

25h 13m

1 stop

$204Multiple Airlines

Thu, Feb 5 - Mon, Feb 9

8:43 pm - 10:19 am

ORD

SWF

12h 36m

1 stop

11:09 am - 10:51 am

SWF

ORD

24h 42m

2 stops

$236Multiple Airlines

Thu, Feb 5 - Mon, Feb 9

5:32 pm - 9:38 am

ORD

SWF

15h 06m

1 stop

12:05 pm - 7:59 am

SWF

ORD

20h 54m

2 stops

$365Multiple Airlines

Wed, Jun 10 - Wed, Jun 17

12:41 pm - 8:58 am

ORD

SWF

19h 17m

1 stop

12:05 pm - 10:08 pm

SWF

ORD

11h 03m

2 stops

$432Multiple Airlines

Wed, Jul 1 - Sat, Jul 11

4:10 pm - 8:58 am

ORD

SWF

15h 48m

1 stop

12:05 pm - 10:08 pm

SWF

ORD

11h 03m

2 stops

$475Multiple Airlines

Sat, Jun 20 - Sat, Jun 27

10:17 am - 11:25 am

ORD

SWF

24h 08m

2 stops

8:00 pm - 7:59 am

SWF

ORD

12h 59m

1 stop

$529Multiple Airlines

Tue, Jun 23 - Sat, Jun 27

10:17 am - 11:25 am

ORD

SWF

24h 08m

2 stops

8:00 pm - 7:59 am

SWF

ORD

12h 59m

1 stop

$530Multiple Airlines

Tue, Jun 23 - Sat, Jun 27

5:05 am - 11:31 am

ORD

SWF

29h 26m

2 stops

11:48 am - 8:00 pm

SWF

ORD

9h 12m

1 stop

$783Multiple Airlines

Thu, Mar 26 - Sun, Mar 29

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 2/9

11:09 am-11:22 am

1 stop25h 13m

$204

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 2/9

11:09 am-10:51 am

2 stops24h 42m

$236

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/10

5:32 pm-9:38 am

1 stop15h 06m

New Windsor Stewart

Wed 6/17

12:05 pm-7:59 am

2 stops20h 54m

$365

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 7/1

12:41 pm-8:58 am

1 stop19h 17m

New Windsor Stewart

Sat 7/11

12:05 pm-10:08 pm

2 stops11h 03m

$432

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 6/20

4:10 pm-8:58 am

1 stop15h 48m

New Windsor Stewart

Sat 6/27

12:05 pm-10:08 pm

2 stops11h 03m

$475

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Tue 6/23

10:17 am-11:25 am

2 stops24h 08m

New Windsor Stewart

Sat 6/27

8:00 pm-7:59 am

1 stop12h 59m

$529

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Tue 6/23

10:17 am-11:25 am

2 stops24h 08m

New Windsor Stewart

Sat 6/27

8:00 pm-7:59 am

1 stop12h 59m

$530

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 3/26

5:05 am-11:31 am

2 stops29h 26m

New Windsor Stewart

Sun 3/29

11:48 am-8:00 pm

1 stop9h 12m

$783

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/4

8:16 pm-9:19 am

1 stop12h 03m

$97

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/14

4:43 pm-10:52 am

1 stop17h 09m

$102

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

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 38% 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	12h 36m
Direct flights	None

The fastest flight from Chicago to New Windsor takes 12h 36m

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 12h 36m 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.

Newburgh

Kingston

Woodstock

Saugerties

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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.