What is the cheapest flight from Chicago to New Windsor?

In the last 3 days, the lowest price for a flight from Chicago to New Windsor was $122 for a one-way ticket and $254 for a round-trip. Visit our flight page for the latest deals!>/a>

Do I need a passport to fly between Chicago and Stewart Intl.?

No, a passport isn't needed to fly from Chicago to Stewart Intl.. However, local authorities might ask for an official ID. Visit our flight page for the latest deals!>/a>

Which airports will I be using when flying from Chicago to Stewart Intl.?

Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. New Windsor Stewart is the only airport in Stewart Intl.. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport. Visit our flight page for the latest deals!>/a>

Which aircraft models fly most regularly from Chicago to Stewart Intl.?

We unfortunately don’t have that data for this specific route.

How does KAYAK find such low prices on flights from Chicago to Stewart Intl.?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Stewart Intl.. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Stewart Intl.?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Chicago is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Chicago to Stewart Intl.?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back to Chicago with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Stewart Intl.?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

$122 CHEAP FLIGHTS from Chicago to New Windsor (CHI - SWF)

CHI - SWF

KAYAK searches hundreds of travel sites at once for deals on flights to New Windsor

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Flights Deals

Cheap Flight Deals from Chicago to New Windsor (CHI-SWF)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to New Windsor that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Chicago to New Windsor

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to New Windsor.

Discover the best prices for you by selecting your travel dates on KAYAK.

9:55 am - 11:05 amORD-SWF

24h 10m1 stop

11:55 am - 8:50 amSWF-ORD

21h 55m1 stop

$254

Find Deal

Thu, May 22 - Mon, May 26

6:30 am - 11:05 amORD-SWF

27h 35m2 stops

7:18 pm - 12:05 amSWF-ORD

29h 47m1 stop

$255

Find Deal

Sun, Jun 1 - Fri, Jun 6

9:55 am - 11:05 amORD-SWF

24h 10m1 stop

7:18 pm - 8:50 amSWF-ORD

14h 32m1 stop

$256

Find Deal

Sun, Jun 1 - Fri, Jun 6

9:55 am - 11:05 amORD-SWF

24h 10m1 stop

11:55 am - 8:50 amSWF-ORD

21h 55m1 stop

$265

Find Deal

Thu, May 15 - Mon, May 19

5:05 am - 7:11 pmORD-SWF

13h 06m1 stop

8:01 pm - 8:50 amSWF-ORD

13h 49m1 stop

$282

Find Deal

Fri, Jun 20 - Mon, Jun 23

1:34 pm - 4:58 pmORD-SWF

26h 24m1 stop

8:01 pm - 8:50 amSWF-ORD

13h 49m1 stop

$285

Find Deal

Fri, Jun 13 - Fri, Jun 20

4:35 pm - 11:05 amORD-SWF

17h 30m2 stops

11:55 am - 8:50 amSWF-ORD

21h 55m1 stop

$289

Find Deal

Thu, May 22 - Mon, May 26

6:30 am - 11:05 amORD-SWF

27h 35m2 stops

7:18 pm - 11:29 pmSWF-ORD

29h 11m2 stops

$291

Find Deal

Sun, Jun 1 - Fri, Jun 6

10:00 am - 11:05 amORD-SWF

24h 05m2 stops

11:55 am - 8:50 amSWF-ORD

21h 55m1 stop

$295

Find Deal

Thu, May 15 - Mon, May 19

7:56 am - 4:58 pmORD-SWF

32h 02m2 stops

8:01 pm - 8:50 amSWF-ORD

13h 49m1 stop

$321

Find Deal

Fri, Jun 13 - Fri, Jun 20

Useful Info

Cheapest flight	$122

Flight from Chicago O'Hare Airport to Stewart Intl.

When to book flights from Chicago to New Windsor

Are your dates flexible? Find out the best times to travel from Chicago to New Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

What is the cheapest flight from Chicago to New Windsor?
In the last 3 days, the lowest price for a flight from Chicago to New Windsor was $122 for a one-way ticket and $254 for a round-trip.
Do I need a passport to fly between Chicago and Stewart Intl.?
No, a passport isn't needed to fly from Chicago to Stewart Intl.. However, local authorities might ask for an official ID.
Which airports will I be using when flying from Chicago to Stewart Intl.?
Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. New Windsor Stewart is the only airport in Stewart Intl.. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.
Which aircraft models fly most regularly from Chicago to Stewart Intl.?
We unfortunately don’t have that data for this specific route.
How does KAYAK find such low prices on flights from Chicago to Stewart Intl.?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Stewart Intl..
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Stewart Intl.?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Chicago to Stewart Intl.?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back to Chicago with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Stewart Intl.?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Chicago to New Windsor

Airports

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Information on your arrival and departure airports

New Windsor (SWF)

CHI - SWF

$122 Find Cheap Flights from Chicago to New Windsor

KAYAK searches hundreds of travel sites at once for deals on flights to New Windsor

Cheap Flight Deals from Chicago to New Windsor (CHI-SWF)

Recent round-trip flight deals from Chicago to New Windsor

Recent one-way flight deals from Chicago to New Windsor

Recent last minute flight deals from Chicago to New Windsor

Good to know

When to book flights from Chicago to New Windsor

FAQs for booking flights from Chicago to Stewart Intl.

What is the cheapest flight from Chicago to New Windsor?

In the last 3 days, the lowest price for a flight from Chicago to New Windsor was $122 for a one-way ticket and $254 for a round-trip.

Do I need a passport to fly between Chicago and Stewart Intl.?

No, a passport isn't needed to fly from Chicago to Stewart Intl.. However, local authorities might ask for an official ID.

Which airports will I be using when flying from Chicago to Stewart Intl.?

Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. New Windsor Stewart is the only airport in Stewart Intl.. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.

Which aircraft models fly most regularly from Chicago to Stewart Intl.?

We unfortunately don’t have that data for this specific route.

How does KAYAK find such low prices on flights from Chicago to Stewart Intl.?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Stewart Intl..

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Stewart Intl.?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Chicago to Stewart Intl.?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back to Chicago with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Stewart Intl.?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Chicago to New Windsor

Information on your arrival and departure airports

Cabin class types available on flights from Chicago to New Windsor

Complete your trip to New Windsor with a hotel stay or car rental

Find direct flights to and from Chicago and New Windsor

Flights to other popular destinations

Flights from domestic origins to New Windsor

Choose which airport to fly into in New Windsor

Find deals for your return flight