What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from New Windsor according to our data. American Airlines is the first choice among our users, with 37% 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

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Find the cheapest flights from New Windsor to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:09 am - 11:42 pmSWF-ORD

13h 33m1 stop

5:59 pm - 10:19 amORD-SWF

15h 20m1 stop

$231Multiple Airlines

Find Deal

Fri, Jan 23 - Sun, Jan 25

11:09 am - 11:42 pmSWF-ORD

13h 33m1 stop

5:59 pm - 10:19 amORD-SWF

15h 20m1 stop

$232Multiple Airlines

Find Deal

Fri, Jan 9 - Sun, Jan 11

12:01 pm - 9:47 amSWF-ORD

22h 46m1 stop

8:26 am - 10:11 amORD-SWF

24h 45m2 stops

$234Multiple Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

12:01 pm - 9:47 amSWF-ORD

22h 46m1 stop

10:52 am - 10:11 amORD-SWF

22h 19m1 stop

$238Multiple Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

11:12 am - 9:17 amSWF-ORD

23h 05m1 stop

11:48 am - 10:07 amORD-SWF

21h 19m1 stop

$245Multiple Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

11:12 am - 9:17 amSWF-ORD

23h 05m1 stop

12:55 pm - 10:07 amORD-SWF

20h 12m2 stops

$273Multiple Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

12:17 pm - 4:25 pmSWF-ORD

29h 08m1 stop

4:01 pm - 11:37 amORD-SWF

42h 36m2 stops

$276Multiple Airlines

Find Deal

Wed, Nov 26 - Wed, Dec 3

11:01 am - 12:27 amSWF-ORD

14h 26m1 stop

3:26 pm - 11:11 amORD-SWF

18h 45m1 stop

$282Multiple Airlines

Find Deal

Fri, Nov 14 - Sun, Nov 16

7:05 pm - 8:53 amSWF-RFD

14h 48m1 stop

9:00 am - 10:26 amRFD-SWF

24h 26m1 stop

$382Allegiant Air

Find Deal

Fri, Nov 14 - Mon, Nov 17

6:02 pm - 9:36 amSWF-RFD

16h 34m1 stop

10:42 am - 6:43 pmRFD-SWF

7h 01m1 stop

$391Allegiant Air

Find Deal

Mon, Jan 26 - Mon, Feb 2

Allegiant Air flights from New Windsor to Chicago

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

Allegiant Air

Nov 14

SWF7:05 pmNew Windsor Stewart

14h 48m

1 stop

RFD8:53 amChicago Greater Rockford

Nov 17

RFD9:00 amChicago Greater Rockford

24h 26m

1 stop

SWF10:26 amNew Windsor Stewart

$382

Find similar

Allegiant Air

Jan 26

SWF6:02 pmNew Windsor Stewart

16h 34m

1 stop

RFD9:36 amChicago Greater Rockford

Feb 2

RFD10:42 amChicago Greater Rockford

7h 01m

1 stop

SWF6:43 pmNew Windsor Stewart

$391

Find similar

Allegiant Air

Jan 3

SWF8:45 pmNew Windsor Stewart

12h 06m

1 stop

RFD7:51 amChicago Greater Rockford

Jan 4

RFD7:24 pmChicago Greater Rockford

13h 06m

1 stop

SWF9:30 amNew Windsor Stewart

$569

Find similar

Fly from

Fly to

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-11:42 pm

1 stop13h 33m

Chicago O'Hare Intl

Sun 1/25

5:59 pm-10:19 am

1 stop15h 20m

$231

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/9

11:09 am-11:42 pm

1 stop13h 33m

Chicago O'Hare Intl

Sun 1/11

5:59 pm-10:19 am

1 stop15h 20m

$232

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Thu 11/13

8:26 am-10:11 am

2 stops24h 45m

$234

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Thu 11/13

10:52 am-10:11 am

1 stop22h 19m

$238

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/21

11:12 am-9:17 am

1 stop23h 05m

Chicago O'Hare Intl

Sun 11/23

11:48 am-10:07 am

1 stop21h 19m

$245

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/21

11:12 am-9:17 am

1 stop23h 05m

Chicago O'Hare Intl

Sun 11/23

12:55 pm-10:07 am

2 stops20h 12m

$273

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 11/26

12:17 pm-4:25 pm

1 stop29h 08m

Chicago O'Hare Intl

Wed 12/3

4:01 pm-11:37 am

2 stops42h 36m

$276

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/14

11:01 am-12:27 am

1 stop14h 26m

Chicago O'Hare Intl

Sun 11/16

3:26 pm-11:11 am

1 stop18h 45m

$282

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 11/14

7:05 pm-8:53 am

1 stop14h 48m

Chicago Greater Rockford

Mon 11/17

9:00 am-10:26 am

1 stop24h 26m

$382

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 1/26

6:02 pm-9:36 am

1 stop16h 34m

Chicago Greater Rockford

Mon 2/2

10:42 am-6:43 pm

1 stop7h 01m

$391

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 $293. 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 $386.

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 $367.

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

Direct flights	None

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

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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 7h 42m, 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.