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Cheap flights from New Windsor to Chicago from $91

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 5/19. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from New Windsor to Chicago.
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11:50 am - 8:50 amSWF-ORD
22h 00m1 stop
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7:35 pm - 11:05 amORD-SWF
14h 30m1 stop
lun., may. 12 - jue., may. 15
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11:50 am - 9:24 amSWF-ORD
22h 34m1 stop
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9:55 am - 11:00 amORD-SWF
24h 05m1 stop
lun., may. 5 - jue., may. 8
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11:50 am - 12:05 amSWF-ORD
13h 15m1 stop
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9:55 am - 11:00 amORD-SWF
24h 05m1 stop
vie., may. 9 - dom., may. 11
Allegiant Air Logo
8:04 pm - 8:08 amSWF-RFD
13h 04m1 stop
Allegiant Air Logo
10:26 am - 9:11 amRFD-SWF
21h 45m1 stop
$266Allegiant Air
Find Deal
jue., may. 1 - dom., may. 4
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11:50 am - 11:29 pmSWF-ORD
12h 39m2 stops
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9:55 am - 11:00 amORD-SWF
24h 05m1 stop
vie., may. 9 - dom., may. 11
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11:50 am - 11:29 pmSWF-ORD
12h 39m2 stops
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9:55 am - 11:00 amORD-SWF
24h 05m1 stop
vie., may. 9 - dom., may. 11
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7:18 pm - 8:50 amSWF-ORD
14h 32m1 stop
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5:05 am - 6:28 pmORD-SWF
12h 23m1 stop
vie., jun. 6 - lun., jun. 9
Allegiant Air Logo
8:04 pm - 8:08 amSWF-RFD
13h 04m1 stop
Allegiant Air Logo
10:26 am - 9:11 amRFD-SWF
21h 45m1 stop
$281Allegiant Air
Find Deal
jue., may. 1 - dom., may. 4
 Logo
7:18 pm - 12:05 amSWF-ORD
29h 47m1 stop
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10:00 am - 6:28 pmORD-SWF
31h 28m2 stops
vie., jun. 6 - dom., jun. 8
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11:55 am - 11:50 amSWF-ORD
24h 55m2 stops
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5:05 am - 11:05 amORD-SWF
29h 00m1 stop
vie., may. 16 - dom., may. 18

Allegiant Air flights from New Windsor to Chicago

Our best Allegiant Air deals on New Windsor to Chicago flight tickets
Allegiant Air
May 1
SWF8:04 pmNew Windsor Stewart
13h 04m
1 stop
RFD8:08 amChicago Greater Rockford
May 4
RFD10:26 amChicago Greater Rockford
21h 45m
1 stop
SWF9:11 amNew Windsor Stewart
Allegiant Air
May 1
SWF8:04 pmNew Windsor Stewart
13h 04m
1 stop
RFD8:08 amChicago Greater Rockford
May 4
RFD10:26 amChicago Greater Rockford
21h 45m
1 stop
SWF9:11 amNew Windsor Stewart
Allegiant Air
Apr 25
SWF10:01 amNew Windsor Stewart
25h 25m
1 stop
RFD10:26 amChicago Greater Rockford
Apr 28
RFD8:58 amChicago Greater Rockford
24h 04m
1 stop
SWF10:02 amNew Windsor Stewart

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 $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 $376.

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 $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $341.

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

Best Price Found

$91

Fastest flight time

8h 10m

Direct flights

None

Airports in Chicago

3 airports
The best one-way flight to Chicago from New Windsor in the past 72 hours is $91. The best round-trip flight deal from New Windsor to Chicago found on momondo in the last 72 hours is $249.
The fastest flight from New Windsor to Chicago takes 8h 10m
There are no direct flights from New Windsor to Chicago. Popular non-direct routes for this connection are New Windsor Stewart Airport - Chicago Midway Airport, New Windsor Stewart Airport - Chicago O'Hare Intl Airport and New Windsor Stewart Airport - Chicago Greater Rockford Airport.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Greater Rockford (RFD), Chicago Midway (MDW)

  • 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 12h 39m, 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.

  • What is the most popular airline from New Windsor to Chicago?


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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.


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1 adult
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mar. 4/22
mar. 4/29

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