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.

$89 Cheap Flights from Chicago to New Windsor in 2026

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11:19 am - 11:08 am

MDW

SWF

22h 49m

1 stop

9:52 am - 11:51 pm

SWF

MDW

14h 59m

1 stop

$281Multiple Airlines

Wed, Mar 11 - Fri, Mar 13

12:44 pm - 11:31 am

ORD

SWF

21h 47m

2 stops

10:09 am - 11:05 pm

SWF

ORD

13h 56m

1 stop

$282Multiple Airlines

Sun, Mar 1 - Thu, Mar 5

6:36 pm - 9:19 am

ORD

SWF

13h 43m

1 stop

9:52 am - 11:38 pm

SWF

ORD

14h 46m

1 stop

$292Multiple Airlines

Wed, Mar 11 - Fri, Mar 13

6:36 pm - 9:19 am

ORD

SWF

13h 43m

1 stop

12:11 pm - 11:38 pm

SWF

ORD

12h 27m

2 stops

$307Multiple Airlines

Wed, Mar 11 - Fri, Mar 13

8:16 pm - 8:19 am

ORD

SWF

11h 03m

1 stop

7:27 pm - 3:35 pm

SWF

ORD

21h 08m

1 stop

$334Multiple Airlines

Sat, Mar 7 - Sun, Mar 8

5:05 am - 11:39 am

ORD

SWF

29h 34m

1 stop

10:29 am - 7:51 pm

SWF

ORD

10h 22m

1 stop

$386Multiple Airlines

Sat, Mar 14 - Thu, Mar 19

6:10 pm - 11:39 am

ORD

SWF

16h 29m

1 stop

10:29 am - 12:13 am

SWF

ORD

14h 44m

2 stops

$417Multiple Airlines

Sat, Mar 14 - Thu, Mar 19

7:06 am - 9:38 am

ORD

SWF

25h 32m

1 stop

12:05 pm - 7:54 am

SWF

ORD

20h 49m

2 stops

$438Multiple Airlines

Wed, Jun 17 - Sat, Jun 20

9:15 am - 11:31 am

ORD

SWF

25h 16m

2 stops

10:29 am - 5:17 pm

SWF

ORD

31h 48m

1 stop

$469Multiple Airlines

Sun, Mar 15 - Sun, Mar 22

12:25 pm - 10:55 am

ORD

SWF

21h 30m

1 stop

11:40 am - 11:36 pm

SWF

ORD

12h 56m

1 stop

$497Multiple Airlines

Sat, Apr 11 - Mon, Apr 13

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 3/11

11:19 am-11:08 am

1 stop22h 49m

New Windsor Stewart

Fri 3/13

9:52 am-11:51 pm

1 stop14h 59m

$281

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 3/1

12:44 pm-11:31 am

2 stops21h 47m

New Windsor Stewart

Thu 3/5

10:09 am-11:05 pm

1 stop13h 56m

$282

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/11

6:36 pm-9:19 am

1 stop13h 43m

New Windsor Stewart

Fri 3/13

9:52 am-11:38 pm

1 stop14h 46m

$292

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/11

6:36 pm-9:19 am

1 stop13h 43m

New Windsor Stewart

Fri 3/13

12:11 pm-11:38 pm

2 stops12h 27m

$307

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/7

8:16 pm-8:19 am

1 stop11h 03m

New Windsor Stewart

Sun 3/8

7:27 pm-3:35 pm

1 stop21h 08m

$334

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/14

5:05 am-11:39 am

1 stop29h 34m

New Windsor Stewart

Thu 3/19

10:29 am-7:51 pm

1 stop10h 22m

$386

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/14

6:10 pm-11:39 am

1 stop16h 29m

New Windsor Stewart

Thu 3/19

10:29 am-12:13 am

2 stops14h 44m

$417

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/17

7:06 am-9:38 am

1 stop25h 32m

New Windsor Stewart

Sat 6/20

12:05 pm-7:54 am

2 stops20h 49m

$438

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 3/15

9:15 am-11:31 am

2 stops25h 16m

New Windsor Stewart

Sun 3/22

10:29 am-5:17 pm

1 stop31h 48m

$469

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 4/11

12:25 pm-10:55 am

1 stop21h 30m

New Windsor Stewart

Mon 4/13

11:40 am-11:36 pm

1 stop12h 56m

$497

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 40% 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

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Fastest flight time	13h 43m
Direct flights	None

The fastest flight from Chicago to New Windsor takes 13h 43m

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 43m 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.

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Cheap flights from Chicago to New York from $89

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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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to New Windsor?

Can I find flights from Chicago to New Windsor with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to New Windsor?

I’m not ready to book a flight from Chicago to New Windsor right now. Can momondo alert me if prices change?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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