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Cheap flights from New Windsor to Chicago from $85

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Chicago departing on 4/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from New Windsor to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
7:15 pm - 10:55 am
ORD
-
SWF
14h 40m
1 stop
$221Multiple Airlines
Thu, Apr 30 - Sat, May 2
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
7:15 pm - 10:55 am
ORD
-
SWF
14h 40m
1 stop
$232Multiple Airlines
Thu, Apr 30 - Sat, May 2
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
7:15 pm - 10:55 am
ORD
-
SWF
14h 40m
1 stop
$240Multiple Airlines
Thu, Apr 30 - Sat, May 2
Multiple Airlines Logo
11:45 am - 9:17 pm
SWF
-
ORD
10h 32m
1 stop
Multiple Airlines Logo
9:16 am - 11:08 am
ORD
-
SWF
24h 52m
2 stops
$272Multiple Airlines
Thu, Apr 30 - Sat, May 2
Multiple Airlines Logo
12:05 pm - 11:19 pm
SWF
-
ORD
12h 14m
2 stops
Multiple Airlines Logo
7:55 am - 9:38 am
ORD
-
SWF
24h 43m
1 stop
$324Multiple Airlines
Sat, Jul 4 - Wed, Jul 15
Multiple Airlines Logo
9:41 am - 11:13 pm
SWF
-
ORD
14h 32m
1 stop
Multiple Airlines Logo
1:50 pm - 11:25 am
ORD
-
SWF
20h 35m
2 stops
$332Multiple Airlines
Fri, May 22 - Tue, May 26
Multiple Airlines Logo
7:46 pm - 9:05 am
SWF
-
ORD
14h 19m
2 stops
Multiple Airlines Logo
1:27 pm - 10:55 am
ORD
-
SWF
20h 28m
1 stop
$340Multiple Airlines
Fri, May 1 - Sat, May 2
Allegiant Air Logo
8:04 pm - 7:45 am
SWF
-
RFD
12h 41m
1 stop
Allegiant Air Logo
10:05 am - 5:54 pm
RFD
-
SWF
6h 49m
1 stop
$344Allegiant Air
Sun, Jun 21 - Sat, Jul 4
Multiple Airlines Logo
8:10 pm - 12:23 pm
SWF
-
ORD
17h 13m
1 stop
Multiple Airlines Logo
1:50 pm - 11:25 am
ORD
-
SWF
20h 35m
2 stops
$358Multiple Airlines
Thu, May 21 - Tue, May 26
Allegiant Air Logo
8:04 pm - 7:45 am
SWF
-
RFD
12h 41m
1 stop
Allegiant Air Logo
10:07 am - 7:10 pm
RFD
-
SWF
8h 03m
1 stop
$397Allegiant Air
Sun, Jun 21 - Sat, Jun 27

Allegiant Air flights from New Windsor to Chicago

Our best Allegiant Air deals on New Windsor to Chicago flight tickets
Allegiant Air
Jun 21
SWF8:04 pmNew Windsor Stewart
12h 41m
1 stop
RFD7:45 amChicago Greater Rockford
Jul 4
RFD10:05 amChicago Greater Rockford
6h 49m
1 stop
SWF5:54 pmNew Windsor Stewart
$344
Allegiant Air
Jun 21
SWF8:04 pmNew Windsor Stewart
12h 41m
1 stop
RFD7:45 amChicago Greater Rockford
Jun 27
RFD10:07 amChicago Greater Rockford
8h 03m
1 stop
SWF7:10 pmNew Windsor Stewart
$397
Allegiant Air
Jun 25
SWF8:04 pmNew Windsor Stewart
12h 41m
1 stop
RFD7:45 amChicago Greater Rockford
Jun 27
RFD10:07 amChicago Greater Rockford
8h 03m
1 stop
SWF7:10 pmNew Windsor Stewart
$496

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/30

11:45 am-9:17 pm

1 stop10h 32m

Chicago O'Hare Intl

Sat 5/2

7:15 pm-10:55 am

1 stop14h 40m

$221

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/30

11:45 am-9:17 pm

1 stop10h 32m

Chicago O'Hare Intl

Sat 5/2

7:15 pm-10:55 am

1 stop14h 40m

$232

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/30

11:45 am-9:17 pm

1 stop10h 32m

Chicago O'Hare Intl

Sat 5/2

7:15 pm-10:55 am

1 stop14h 40m

$240

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/30

11:45 am-9:17 pm

1 stop10h 32m

Chicago O'Hare Intl

Sat 5/2

9:16 am-11:08 am

2 stops24h 52m

$272

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sat 7/4

12:05 pm-11:19 pm

2 stops12h 14m

Chicago O'Hare Intl

Wed 7/15

7:55 am-9:38 am

1 stop24h 43m

$324

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/22

9:41 am-11:13 pm

1 stop14h 32m

Chicago O'Hare Intl

Tue 5/26

1:50 pm-11:25 am

2 stops20h 35m

$332

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/1

7:46 pm-9:05 am

2 stops14h 19m

Chicago O'Hare Intl

Sat 5/2

1:27 pm-10:55 am

1 stop20h 28m

$340
Quickest round-trip

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 6/21

8:04 pm-7:45 am

1 stop12h 41m

Chicago Greater Rockford

Sat 7/4

10:05 am-5:54 pm

1 stop6h 49m

$344

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/21

8:10 pm-12:23 pm

1 stop17h 13m

Chicago O'Hare Intl

Tue 5/26

1:50 pm-11:25 am

2 stops20h 35m

$358

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 6/21

8:04 pm-7:45 am

1 stop12h 41m

Chicago Greater Rockford

Sat 6/27

10:07 am-7:10 pm

1 stop8h 03m

$397

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

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 Saturday when prices can be found for as low as $290. 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 $366.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $360.

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

10h 32m

Direct flights

None
The fastest flight from New Windsor to Chicago takes 10h 32m
There are no direct flights from New Windsor to Chicago. There are no popular flight routes from New Windsor to Chicago.
Search flight deals

Frequently asked questions about flying from New Windsor to Chicago

  • 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 10h 32m, 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport