What airlines fly to Chicago?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from New Windsor according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from New Windsor Stewart to Chicago?

Allegiant Air is the most popular carrier operating from New Windsor Stewart to Chicago

When did momondo last update prices for flights from New Windsor Stewart Airport to Chicago?

Prices for flights from New Windsor Stewart Airport to Chicago are updated daily.

How old do you have to be to fly from New Windsor Stewart Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New Windsor Stewart Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$80 Cheap Flights from New Windsor to Chicago in 2025/26

1 adult

0 bags

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Find the cheapest flights from New Windsor to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

5:38 pm - 9:39 am

ORD

SWF

15h 01m1 stop

$407Multiple Airlines

Thu, Apr 2 - Sat, Apr 4

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

4:00 pm - 11:49 am

ORD

SWF

18h 49m1 stop

$546Multiple Airlines

Thu, Apr 2 - Mon, Apr 6

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

11:39 am - 11:49 am

ORD

SWF

23h 10m2 stops

$580Multiple Airlines

Thu, Apr 2 - Mon, Apr 6

7:50 pm - 9:23 am

SWF

MDW

14h 33m1 stop

10:50 pm - 11:03 am

MDW

SWF

35h 13m2 stops

$618Multiple Airlines

Sat, Dec 20 - Sun, Dec 21

8:12 pm - 5:27 pm

SWF

RFD

22h 15m1 stop

6:17 pm - 11:49 am

RFD

SWF

16h 32m1 stop

$699Allegiant Air

Thu, Apr 2 - Mon, Apr 6

5:28 pm - 8:53 am

SWF

MDW

16h 25m1 stop

6:12 am - 10:47 am

MDW

SWF

51h 35m2 stops

$699Multiple Airlines

Mon, Dec 22 - Sat, Dec 27

11:57 am - 12:30 am

SWF

ORD

13h 33m1 stop

5:29 pm - 5:59 pm

ORD

SWF

47h 30m2 stops

$716Multiple Airlines

Fri, Jan 2 - Tue, Jan 6

5:28 pm - 8:53 am

SWF

MDW

16h 25m1 stop

2:16 pm - 11:03 am

MDW

SWF

19h 47m1 stop

$752Multiple Airlines

Mon, Dec 22 - Sat, Dec 27

8:45 pm - 7:51 am

SWF

RFD

12h 06m1 stop

7:24 pm - 9:30 am

RFD

SWF

13h 06m1 stop

$783Allegiant Air

Sat, Jan 3 - Sun, Jan 4

11:57 am - 6:39 pm

SWF

ORD

7h 42m1 stop

7:20 am - 10:47 am

ORD

SWF

26h 27m2 stops

$835Multiple Airlines

Fri, Jan 2 - Sun, Jan 4

Allegiant Air flights from New Windsor to Chicago

Our best Allegiant Air deals on New Windsor to Chicago flight tickets

Allegiant Air

Dec 27

SWF8:45 pmNew Windsor Stewart

12h 06m

1 stop

RFD7:51 amChicago Greater Rockford

Dec 30

RFD7:54 pmChicago Greater Rockford

19h 50m

1 stop

SWF4:44 pmNew Windsor Stewart

$642

Find similar

Allegiant Air

Dec 27

SWF8:45 pmNew Windsor Stewart

12h 06m

1 stop

RFD7:51 amChicago Greater Rockford

Dec 30

RFD7:54 pmChicago Greater Rockford

19h 50m

1 stop

SWF4:44 pmNew Windsor Stewart

$676

Find similar

Allegiant Air

Dec 27

SWF8:45 pmNew Windsor Stewart

12h 06m

1 stop

RFD7:51 amChicago Greater Rockford

Dec 30

RFD7:54 pmChicago Greater Rockford

19h 50m

1 stop

SWF4:44 pmNew Windsor Stewart

$716

Find similar

Fly from

Fly to

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/2

10:29 am-11:41 pm

1 stop14h 12m

Chicago O'Hare Intl

Sat 4/4

5:38 pm-9:39 am

1 stop15h 01m

$407

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/2

10:29 am-11:41 pm

1 stop14h 12m

Chicago O'Hare Intl

Mon 4/6

4:00 pm-11:49 am

1 stop18h 49m

$546

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/2

10:29 am-11:41 pm

1 stop14h 12m

Chicago O'Hare Intl

Mon 4/6

11:39 am-11:49 am

2 stops23h 10m

$580

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sat 12/20

7:50 pm-9:23 am

1 stop14h 33m

Chicago Midway

Sun 12/21

10:50 pm-11:03 am

2 stops35h 13m

$618

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 4/2

8:12 pm-5:27 pm

1 stop22h 15m

Chicago Greater Rockford

Mon 4/6

6:17 pm-11:49 am

1 stop16h 32m

$699

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Mon 12/22

5:28 pm-8:53 am

1 stop16h 25m

Chicago Midway

Sat 12/27

6:12 am-10:47 am

2 stops51h 35m

$699

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/2

11:57 am-12:30 am

1 stop13h 33m

Chicago O'Hare Intl

Tue 1/6

5:29 pm-5:59 pm

2 stops47h 30m

$716

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Mon 12/22

5:28 pm-8:53 am

1 stop16h 25m

Chicago Midway

Sat 12/27

2:16 pm-11:03 am

1 stop19h 47m

$752

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sat 1/3

8:45 pm-7:51 am

1 stop12h 06m

Chicago Greater Rockford

Sun 1/4

7:24 pm-9:30 am

1 stop13h 06m

$783

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/2

11:57 am-6:39 pm

1 stop7h 42m

Chicago O'Hare Intl

Sun 1/4

7:20 am-10:47 am

2 stops26h 27m

$835

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 New Windsor to Chicago

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

Prices

Airlines

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from New Windsor to Chicago for around $372.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New Windsor to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

When to book flights from New Windsor to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from New Windsor to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap New Windsor to Chicago (SWF to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Chicago

Fastest flight time	9h 04m
Direct flights	None

The fastest flight from New Windsor to Chicago takes 9h 04m

There are no direct flights from New Windsor to Chicago. There are no popular flight routes from New Windsor to Chicago.

Search flight deals

How far is New Windsor Stewart to Chicago by plane?
There are 701.4 mi between New Windsor Stewart and Chicago. Flights usually cover this in 9h 04m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from New Windsor Stewart Airport to Chicago?
Prices for flights from New Windsor Stewart Airport to Chicago are updated daily.
How old do you have to be to fly from New Windsor Stewart Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New Windsor Stewart Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for New Windsor to Chicago flights to just show those with flexible booking policies.

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

Once all potential New Windsor to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of New Windsor to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.