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.

$95 Cheap Flights from Chicago to New Windsor in 2026

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Cheap round-trip flights

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8:43 pm - 10:19 am

ORD

SWF

12h 36m

1 stop

11:09 am - 11:47 am

SWF

ORD

25h 38m

2 stops

$211Multiple Airlines

週四, 1月 29 - 週一, 2月 2

8:43 pm - 10:19 am

ORD

SWF

12h 36m

1 stop

11:09 am - 11:22 am

SWF

ORD

25h 13m

1 stop

$216Multiple Airlines

週四, 1月 29 - 週一, 2月 2

6:05 am - 11:33 am

ORD

SWF

28h 28m

1 stop

11:09 am - 11:47 am

SWF

ORD

25h 38m

2 stops

$245Multiple Airlines

週三, 1月 28 - 週一, 2月 2

6:05 am - 11:33 am

ORD

SWF

28h 28m

1 stop

11:09 am - 11:47 pm

SWF

ORD

13h 38m

1 stop

$263Multiple Airlines

週三, 1月 28 - 週一, 2月 2

2:52 pm - 10:19 am

ORD

SWF

18h 27m

1 stop

11:48 am - 10:41 am

SWF

ORD

23h 53m

1 stop

$273Multiple Airlines

週四, 2月 5 - 週日, 2月 8

2:52 pm - 10:19 am

ORD

SWF

18h 27m

1 stop

11:48 am - 11:47 pm

SWF

ORD

12h 59m

2 stops

$336Multiple Airlines

週四, 2月 5 - 週日, 2月 8

8:16 pm - 8:19 am

ORD

SWF

11h 03m

1 stop

11:48 am - 11:38 pm

SWF

ORD

12h 50m

1 stop

$386Multiple Airlines

週六, 3月 7 - 週日, 3月 8

4:44 pm - 8:19 am

ORD

SWF

14h 35m

2 stops

11:48 am - 11:38 pm

SWF

ORD

12h 50m

1 stop

$443Multiple Airlines

週六, 3月 7 - 週日, 3月 8

12:06 pm - 10:52 am

ORD

SWF

21h 46m

1 stop

12:11 pm - 11:22 am

SWF

ORD

24h 11m

2 stops

$450Multiple Airlines

週六, 2月 14 - 週一, 2月 16

4:43 pm - 10:52 am

ORD

SWF

17h 09m

1 stop

11:04 am - 3:52 pm

SWF

ORD

29h 48m

1 stop

$459Multiple Airlines

週六, 2月 14 - 週一, 2月 16

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週四 1/29

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

週一 2/2

11:09 am-11:47 am

2 stops25h 38m

$211

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週四 1/29

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

週一 2/2

11:09 am-11:22 am

1 stop25h 13m

$216

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週三 1/28

6:05 am-11:33 am

1 stop28h 28m

New Windsor Stewart

週一 2/2

11:09 am-11:47 am

2 stops25h 38m

$245

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週三 1/28

6:05 am-11:33 am

1 stop28h 28m

New Windsor Stewart

週一 2/2

11:09 am-11:47 pm

1 stop13h 38m

$263

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週四 2/5

2:52 pm-10:19 am

1 stop18h 27m

New Windsor Stewart

週日 2/8

11:48 am-10:41 am

1 stop23h 53m

$273

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週四 2/5

2:52 pm-10:19 am

1 stop18h 27m

New Windsor Stewart

週日 2/8

11:48 am-11:47 pm

2 stops12h 59m

$336

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週六 3/7

8:16 pm-8:19 am

1 stop11h 03m

New Windsor Stewart

週日 3/8

11:48 am-11:38 pm

1 stop12h 50m

$386

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週六 3/7

4:44 pm-8:19 am

2 stops14h 35m

New Windsor Stewart

週日 3/8

11:48 am-11:38 pm

1 stop12h 50m

$443

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週六 2/14

12:06 pm-10:52 am

1 stop21h 46m

New Windsor Stewart

週一 2/16

12:11 pm-11:22 am

2 stops24h 11m

$450

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

週六 2/14

4:43 pm-10:52 am

1 stop17h 09m

New Windsor Stewart

週一 2/16

11:04 am-3:52 pm

1 stop29h 48m

$459

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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	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.

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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.