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.

$91 Cheap Flights from Chicago to New Windsor in 2026

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8:43 pm - 10:19 am

ORD

SWF

12h 36m1 stop

11:09 am - 9:03 pm

SWF

ORD

10h 54m1 stop

$249Multiple Airlines

Thu, Jan 22 - Mon, Jan 26

8:43 pm - 10:19 am

ORD

SWF

12h 36m1 stop

11:42 am - 9:13 pm

SWF

ORD

10h 31m1 stop

$293Multiple Airlines

Thu, Feb 5 - Thu, Feb 12

7:00 am - 11:31 am

ORD

SWF

27h 31m2 stops

11:48 am - 3:28 pm

SWF

ORD

28h 40m1 stop

$355Multiple Airlines

Sun, Mar 1 - Sun, Mar 8

4:43 pm - 10:52 am

ORD

SWF

17h 09m1 stop

11:04 am - 3:52 pm

SWF

ORD

29h 48m1 stop

$389Multiple Airlines

Sat, Feb 14 - Mon, Feb 16

12:44 pm - 11:08 am

ORD

SWF

21h 24m1 stop

11:04 am - 11:22 am

SWF

ORD

25h 18m2 stops

$419Multiple Airlines

Sat, Feb 14 - Mon, Feb 16

12:44 pm - 12:39 pm

ORD

SWF

22h 55m1 stop

12:11 pm - 11:22 am

SWF

ORD

24h 11m2 stops

$466Multiple Airlines

Fri, Feb 13 - Mon, Feb 16

5:38 pm - 9:39 am

ORD

SWF

15h 01m1 stop

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

$720Multiple Airlines

Sat, Mar 28 - Sun, Apr 5

7:30 am - 12:39 pm

MDW

SWF

28h 09m1 stop

12:11 pm - 8:27 pm

SWF

MDW

9h 16m2 stops

$907Multiple Airlines

Fri, Feb 13 - Mon, Feb 16

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/22

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 1/26

11:09 am-9:03 pm

1 stop10h 54m

$249

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Thu 2/12

11:42 am-9:13 pm

1 stop10h 31m

$293

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 3/1

7:00 am-11:31 am

2 stops27h 31m

New Windsor Stewart

Sun 3/8

11:48 am-3:28 pm

1 stop28h 40m

$355

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/14

4:43 pm-10:52 am

1 stop17h 09m

New Windsor Stewart

Mon 2/16

11:04 am-3:52 pm

1 stop29h 48m

$389

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/14

12:44 pm-11:08 am

1 stop21h 24m

New Windsor Stewart

Mon 2/16

11:04 am-11:22 am

2 stops25h 18m

$419

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/13

12:44 pm-12:39 pm

1 stop22h 55m

New Windsor Stewart

Mon 2/16

12:11 pm-11:22 am

2 stops24h 11m

$466

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/28

5:38 pm-9:39 am

1 stop15h 01m

New Windsor Stewart

Sun 4/5

10:29 am-11:41 pm

1 stop14h 12m

$720

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 2/13

7:30 am-12:39 pm

1 stop28h 09m

New Windsor Stewart

Mon 2/16

12:11 pm-8:27 pm

2 stops9h 16m

$907

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/29

8:43 pm-10:19 am

1 stop12h 36m

$91

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 2/8

1:00 pm-6:43 pm

1 stop28h 43m

$92

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.