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Cheap flights from New Windsor to Chicago from $70

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 10/29. 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
1 adult, Economy, 0 bags

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
10:38 am - 3:24 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
4:44 pm - 11:16 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
17h 32m1 stop Orlando
$206Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
10:38 am - 3:24 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
4:44 pm - 11:16 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
17h 32m1 stop Orlando
$210Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
10:38 am - 3:24 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
4:44 pm - 11:16 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
17h 32m1 stop Orlando
$211Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
11:56 am - 8:08 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
33h 12m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:14 am - 6:40 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
9h 26m1 stop Fort Lauderdale
$237Multiple Airlines
Mon, Aug 31 - Thu, Sep 3
Multiple Airlines Logo
7:01 pm - 11:50 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
29h 49m1 stop Orlando Sanford Intl
Multiple Airlines Logo
4:44 pm - 11:16 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
17h 32m1 stop Orlando
$237Multiple Airlines
Mon, Oct 26 - Sat, Oct 31
Multiple Airlines Logo
7:01 pm - 12:02 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 01m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
4:44 pm - 11:16 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
17h 32m1 stop Orlando
$241Multiple Airlines
Mon, Oct 26 - Sat, Oct 31
Multiple Airlines Logo
7:01 pm - 12:02 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 01m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
4:44 pm - 4:49 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
23h 05m1 stop Orlando
$244Multiple Airlines
Mon, Oct 26 - Thu, Oct 29
Multiple Airlines Logo
7:01 pm - 12:02 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
18h 01m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
4:44 pm - 4:49 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
23h 05m1 stop Orlando
$254Multiple Airlines
Mon, Oct 26 - Thu, Oct 29
Multiple Airlines Logo
10:18 am - 3:26 pmSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
30h 08m1 stop Fort Lauderdale
Multiple Airlines Logo
9:33 pm - 9:28 amORD  Chicago O'Hare Intl-SWF New Windsor Stewart
34h 55m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$255Multiple Airlines
Thu, Oct 8 - Tue, Oct 13
Multiple Airlines Logo
7:31 pm - 7:53 amSWF  New Windsor Stewart-ORD Chicago O'Hare Intl
37h 22m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:05 am - 6:40 pmORD  Chicago O'Hare Intl-SWF New Windsor Stewart
9h 35m1 stop Fort Lauderdale
$259Multiple Airlines
Sun, Aug 30 - Sun, Sep 6

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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 August 16, 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 New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Thu 10/29

10:38 am-3:24 pm

1 stop29h 46m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-11:16 am

1 stop17h 32m

$206

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Thu 10/29

10:38 am-3:24 pm

1 stop29h 46m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-11:16 am

1 stop17h 32m

$210

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Thu 10/29

10:38 am-3:24 pm

1 stop29h 46m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-11:16 am

1 stop17h 32m

$211

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Mon 8/31

11:56 am-8:08 pm

2 stops33h 12m

Chicago O'Hare Intl

Thu 9/3

8:14 am-6:40 pm

1 stop9h 26m

$237

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Mon 10/26

7:01 pm-11:50 pm

1 stop29h 49m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-11:16 am

1 stop17h 32m

$237
Quickest round-trip

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Mon 10/26

7:01 pm-12:02 pm

2 stops18h 01m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-11:16 am

1 stop17h 32m

$241

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Mon 10/26

7:01 pm-12:02 pm

2 stops18h 01m

Chicago O'Hare Intl

Thu 10/29

4:44 pm-4:49 pm

1 stop23h 05m

$244

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Mon 10/26

7:01 pm-12:02 pm

2 stops18h 01m

Chicago O'Hare Intl

Thu 10/29

4:44 pm-4:49 pm

1 stop23h 05m

$254

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Thu 10/8

10:18 am-3:26 pm

1 stop30h 08m

Chicago O'Hare Intl

Tue 10/13

9:33 pm-9:28 am

2 stops34h 55m

$255

New WindsorChicago

SWF New Windsor Stewart - ORD Chicago O'Hare Intl

SWFORD

New Windsor Stewart

Sun 8/30

7:31 pm-7:53 am

2 stops37h 22m

Chicago O'Hare Intl

Sun 9/6

8:05 am-6:40 pm

1 stop9h 35m

$259

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 $323. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from New Windsor to Chicago for around $408.

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 $314. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $373.

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

8h 37m

Direct flights

None
The fastest flight from New Windsor to Chicago takes 8h 37m
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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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 8h 37m, 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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