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Cheap flights from New Windsor to Chicago from $88

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
10:28 am - 3:14 pm
SWF
-
ORD
29h 46m
1 stop
Multiple Airlines Logo
8:52 pm - 11:25 am
ORD
-
SWF
13h 33m
2 stops
$296Multiple Airlines
Thu, May 21 - Tue, May 26
Multiple Airlines Logo
12:29 pm - 5:14 pm
SWF
-
ORD
29h 45m
1 stop
Multiple Airlines Logo
9:30 am - 11:31 am
ORD
-
SWF
25h 01m
2 stops
$350Multiple Airlines
Sun, Mar 15 - Thu, Mar 19
Multiple Airlines Logo
10:28 am - 3:14 pm
SWF
-
ORD
29h 46m
1 stop
Multiple Airlines Logo
5:14 pm - 8:51 am
ORD
-
SWF
14h 37m
1 stop
$356Multiple Airlines
Thu, May 21 - Sun, May 24
Multiple Airlines Logo
11:45 am - 11:07 pm
SWF
-
ORD
12h 22m
1 stop
Multiple Airlines Logo
10:31 am - 10:55 am
ORD
-
SWF
23h 24m
1 stop
$383Multiple Airlines
Fri, May 8 - Sun, May 10
Allegiant Air Logo
11:45 am - 7:49 am
SWF
-
RFD
21h 04m
1 stop
Allegiant Air Logo
10:05 am - 5:54 pm
RFD
-
SWF
6h 49m
1 stop
$386Allegiant Air
Thu, Jul 2 - Sat, Jul 4
Multiple Airlines Logo
11:45 am - 7:49 am
SWF
-
RFD
21h 04m
1 stop
Multiple Airlines Logo
7:50 pm - 11:08 am
RFD
-
SWF
14h 18m
1 stop
$393Multiple Airlines
Thu, Jul 2 - Mon, Jul 6
Multiple Airlines Logo
11:45 am - 11:07 pm
SWF
-
ORD
12h 22m
1 stop
Multiple Airlines Logo
11:28 am - 10:55 am
ORD
-
SWF
22h 27m
2 stops
$398Multiple Airlines
Fri, May 8 - Sun, May 10
Multiple Airlines Logo
9:38 am - 6:36 pm
SWF
-
MDW
9h 58m
1 stop
Multiple Airlines Logo
7:41 pm - 8:49 am
MDW
-
SWF
12h 08m
1 stop
$446Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
Multiple Airlines Logo
9:38 am - 6:36 pm
SWF
-
MDW
9h 58m
1 stop
Multiple Airlines Logo
7:41 pm - 11:08 am
MDW
-
SWF
14h 27m
1 stop
$462Multiple Airlines
Thu, Jun 25 - Mon, Jun 29
Allegiant Air Logo
8:40 pm - 6:33 pm
SWF
-
RFD
22h 53m
1 stop
Allegiant Air Logo
7:42 pm - 7:01 pm
RFD
-
SWF
22h 19m
1 stop
$656Allegiant Air
Sun, Mar 15 - Thu, Mar 19

Allegiant Air flights from New Windsor to Chicago

Our best Allegiant Air deals on New Windsor to Chicago flight tickets
Allegiant Air
Mar 15
SWF8:40 pmNew Windsor Stewart
22h 53m
1 stop
RFD6:33 pmChicago Greater Rockford
Mar 19
RFD7:42 pmChicago Greater Rockford
22h 19m
1 stop
SWF7:01 pmNew Windsor Stewart
$656
Allegiant Air
Mar 27
SWF7:51 pmNew Windsor Stewart
13h 13m
1 stop
RFD8:04 amChicago Greater Rockford
Mar 30
RFD7:18 pmChicago Greater Rockford
15h 34m
1 stop
SWF11:52 amNew Windsor Stewart
$679

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 March 1, 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

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/21

10:28 am-3:14 pm

1 stop29h 46m

Chicago O'Hare Intl

Tue 5/26

8:52 pm-11:25 am

2 stops13h 33m

$296

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 3/15

12:29 pm-5:14 pm

1 stop29h 45m

Chicago O'Hare Intl

Thu 3/19

9:30 am-11:31 am

2 stops25h 01m

$350

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/21

10:28 am-3:14 pm

1 stop29h 46m

Chicago O'Hare Intl

Sun 5/24

5:14 pm-8:51 am

1 stop14h 37m

$356

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/8

11:45 am-11:07 pm

1 stop12h 22m

Chicago O'Hare Intl

Sun 5/10

10:31 am-10:55 am

1 stop23h 24m

$383

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 7/2

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Sat 7/4

10:05 am-5:54 pm

1 stop6h 49m

$386

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 7/2

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Mon 7/6

7:50 pm-11:08 am

1 stop14h 18m

$393

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/8

11:45 am-11:07 pm

1 stop12h 22m

Chicago O'Hare Intl

Sun 5/10

11:28 am-10:55 am

2 stops22h 27m

$398

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 6/18

9:38 am-6:36 pm

1 stop9h 58m

Chicago Midway

Sun 6/21

7:41 pm-8:49 am

1 stop12h 08m

$446

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 6/25

9:38 am-6:36 pm

1 stop9h 58m

Chicago Midway

Mon 6/29

7:41 pm-11:08 am

1 stop14h 27m

$462

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 3/15

8:40 pm-6:33 pm

1 stop22h 53m

Chicago Greater Rockford

Thu 3/19

7:42 pm-7:01 pm

1 stop22h 19m

$656

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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 Wednesday when prices can be found for as low as $289. 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 $364.

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 $269. 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

9h 58m

Direct flights

None
The fastest flight from New Windsor to Chicago takes 9h 58m
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 58m, 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
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Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
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