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.

$98 Cheap Flights from Chicago to New Windsor in 2026

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3:05 pm - 10:19 am

ORD

SWF

18h 14m

1 stop

11:09 am - 11:47 pm

SWF

ORD

13h 38m

1 stop

$269Multiple Airlines

Sun, Feb 1 - Fri, Feb 6

8:43 pm - 10:19 am

ORD

SWF

12h 36m

1 stop

12:11 pm - 4:40 pm

SWF

ORD

29h 29m

2 stops

$286Multiple Airlines

Sun, Feb 1 - Fri, Feb 6

8:10 am - 11:08 am

ORD

SWF

25h 58m

2 stops

11:48 am - 7:41 pm

SWF

ORD

8h 53m

1 stop

$329Multiple Airlines

Wed, Feb 4 - Sun, Feb 8

9:25 am - 11:08 am

ORD

SWF

24h 43m

1 stop

11:42 am - 11:24 pm

SWF

ORD

12h 42m

1 stop

$368Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

10:48 am - 11:08 am

ORD

SWF

23h 20m

1 stop

11:42 am - 11:24 pm

SWF

ORD

12h 42m

1 stop

$380Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

5:32 pm - 11:08 am

ORD

SWF

16h 36m

2 stops

11:42 am - 11:24 pm

SWF

ORD

12h 42m

1 stop

$383Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

5:32 pm - 11:08 am

ORD

SWF

16h 36m

2 stops

11:42 am - 11:24 pm

SWF

ORD

12h 42m

1 stop

$390Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

12:44 pm - 11:08 am

ORD

SWF

21h 24m

1 stop

11:48 am - 7:41 pm

SWF

ORD

8h 53m

1 stop

$411Multiple Airlines

Wed, Feb 4 - Sun, Feb 8

9:07 pm - 12:39 pm

ORD

SWF

14h 32m

1 stop

11:52 am - 7:54 am

SWF

ORD

21h 02m

2 stops

$492Multiple Airlines

Fri, Feb 20 - Sun, Feb 22

5:24 pm - 12:39 pm

ORD

SWF

18h 15m

2 stops

11:42 am - 11:47 pm

SWF

ORD

13h 05m

1 stop

$501Multiple Airlines

Fri, Feb 13 - Sun, Feb 15

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 2/1

3:05 pm-10:19 am

1 stop18h 14m

New Windsor Stewart

Fri 2/6

11:09 am-11:47 pm

1 stop13h 38m

$269

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 2/1

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Fri 2/6

12:11 pm-4:40 pm

2 stops29h 29m

$286

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 2/4

8:10 am-11:08 am

2 stops25h 58m

New Windsor Stewart

Sun 2/8

11:48 am-7:41 pm

1 stop8h 53m

$329

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/7

9:25 am-11:08 am

1 stop24h 43m

New Windsor Stewart

Thu 2/12

11:42 am-11:24 pm

1 stop12h 42m

$368

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/7

10:48 am-11:08 am

1 stop23h 20m

New Windsor Stewart

Thu 2/12

11:42 am-11:24 pm

1 stop12h 42m

$380

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/7

5:32 pm-11:08 am

2 stops16h 36m

New Windsor Stewart

Thu 2/12

11:42 am-11:24 pm

1 stop12h 42m

$383

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/7

5:32 pm-11:08 am

2 stops16h 36m

New Windsor Stewart

Thu 2/12

11:42 am-11:24 pm

1 stop12h 42m

$390

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 2/4

12:44 pm-11:08 am

1 stop21h 24m

New Windsor Stewart

Sun 2/8

11:48 am-7:41 pm

1 stop8h 53m

$411

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/20

9:07 pm-12:39 pm

1 stop14h 32m

New Windsor Stewart

Sun 2/22

11:52 am-7:54 am

2 stops21h 02m

$492

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/13

5:24 pm-12:39 pm

2 stops18h 15m

New Windsor Stewart

Sun 2/15

11:42 am-11:47 pm

1 stop13h 05m

$501

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	13h 40m
Direct flights	None

The fastest flight from Chicago to New Windsor takes 13h 40m

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 13h 40m 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.