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Cheap flights from New Windsor to Chicago from $95

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 4/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Wed 4/3
Wed 4/10
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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

$95

Fastest flight time

7h 08m

Direct flights

None

Airports in Chicago

3 airports
The best one-way flight to Chicago from New Windsor in the past 72 hours is $95. The best round-trip flight deal from New Windsor to Chicago found on momondo in the last 72 hours is $298.
The fastest flight from New Windsor to Chicago takes 7h 08m
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 Midway (MDW), Chicago Greater Rockford (RFD)

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 month to fly from New Windsor to Chicago?

February. The cheapest time of year to fly to Chicago from New Windsor is February. Most expensive is July

What is the cheapest day to depart New Windsor for Chicago?

Thursday. The cheapest day of the week is typically Thursday. The most expensive is typically Thursday

When is the cheapest time to fly from New Windsor to Chicago?

New Windsor to Chicago flights are currently only available in the morning

What is the cheapest New Windsor to Chicago flight route?

New Windsor Stewart - Chicago O'Hare Intl. Fly from New Windsor Stewart to Chicago O'Hare Intl for the best New Windsor - Chicago flight prices

When you’re planning your trip from New Windsor to Chicago, the most popular airport-to-airport route is New Windsor Stewart Airport to Chicago O'Hare Intl Airport. When booking your trip to Chicago, it is helpful to have an alternative airport to fly out of. Good options for departure airports when traveling to Chicago, you can try Newark Airport (in Newark), New York John F Kennedy Intl Airport (in New York), or New York LaGuardia Airport (in New York). When traveling from New Windsor, it is helpful to have an alternative airport to fly into when you land in Chicago. Good options for arrival airports in Chicago, you can try Chicago Midway Airport (in Chicago) or Chicago Greater Rockford Airport (in Chicago). In March, $50 is typically the cheapest round trip price you’ll find from New Windsor to Chicago which you can find when you fly LGA — ORD.

Newark Airport (EWR) to Chicago O'Hare Intl Airport (ORD)$117
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New York John F Kennedy Intl Airport (JFK) to Chicago O'Hare Intl Airport (ORD)$127
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New York LaGuardia Airport (LGA) to Chicago O'Hare Intl Airport (ORD)$50
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New York John F Kennedy Intl Airport (JFK) to Chicago Midway Airport (MDW)$298
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New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW)$106
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Newark Airport (EWR) to Chicago Midway Airport (MDW)$158
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Easily compare round-trip flights from New Windsor to Chicago

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from New Windsor to Chicago by changing tabs
Multiple Airlines
May 19
SWF10:25 amNew Windsor Stewart
12h 47m
1 stop
ORD10:12 pmChicago O'Hare Intl
May 22
ORD5:56 pmChicago O'Hare Intl
14h 49m
1 stop
SWF9:45 amNew Windsor Stewart
Multiple Airlines
May 19
SWF10:25 amNew Windsor Stewart
10h 20m
1 stop
ORD7:45 pmChicago O'Hare Intl
May 22
ORD7:13 pmChicago O'Hare Intl
13h 32m
2 stops
SWF9:45 amNew Windsor Stewart
Multiple Airlines
Apr 21
SWF10:30 amNew Windsor Stewart
8h 07m
1 stop
MDW5:37 pmChicago Midway
Apr 27
MDW8:17 pmChicago Midway
12h 33m
1 stop
SWF9:50 amNew Windsor Stewart
Multiple Airlines
Apr 24
SWF7:15 pmNew Windsor Stewart
39h 23m
3 stops
ORD9:38 amChicago O'Hare Intl
May 1
ORD5:00 amChicago O'Hare Intl
27h 45m
2 stops
SWF9:45 amNew Windsor Stewart
Multiple Airlines
Apr 1
SWF12:46 pmNew Windsor Stewart
20h 44m
2 stops
ORD8:30 amChicago O'Hare Intl
Apr 3
ORD4:59 pmChicago O'Hare Intl
15h 51m
1 stop
SWF9:50 amNew Windsor Stewart
Multiple Airlines
Apr 24
SWF7:15 pmNew Windsor Stewart
39h 23m
3 stops
ORD9:38 amChicago O'Hare Intl
May 1
ORD7:03 amChicago O'Hare Intl
25h 42m
3 stops
SWF9:45 amNew Windsor Stewart

Find the cheapest one-way flights from New Windsor to Chicago

If you're looking for one-way flights from New Windsor to Chicago, view some of our deals below provided by Allegiant Air
Multiple Airlines
Apr 8
SWF8:52 pmNew Windsor Stewart
18h 29m
1 stop
MDW2:21 pmChicago Midway
Allegiant Air
Jul 4
SWF7:30 pmNew Windsor Stewart
24h 49m
1 stop
RFD7:19 pmChicago Greater Rockford
Multiple Airlines
Apr 8
SWF8:52 pmNew Windsor Stewart
16h 09m
1 stop
ORD12:01 pmChicago O'Hare Intl

Search last-minute flights to Chicago from New Windsor

Find and compare round-trip flight prices for your last-minute flight from New Windsor to Chicago
Allegiant Air
Apr 4
SWF11:13 amNew Windsor Stewart
23h 32m
1 stop
RFD9:45 amChicago Greater Rockford
Apr 7
RFD7:18 pmChicago Greater Rockford
22h 14m
1 stop
SWF6:32 pmNew Windsor Stewart

  • 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 07m, 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.


Alternative routes for New Windsor to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
New York to Chicago Flights
Fastest flight time2h 34m
Cheapest price$50
New York to St. Louis Flights
Fastest flight time2h 37m
Cheapest price$158
Buffalo to Chicago Flights
Fastest flight time1h 48m
Cheapest price$155
Rochester, New York to Chicago Flights
Fastest flight time1h 58m
Cheapest price$208
Albany, New York to Chicago Flights
Fastest flight time2h 24m
Cheapest price$176
Syracuse to Chicago Flights
Fastest flight time3h 32m
Cheapest price$186
White Plains to Chicago Flights
Fastest flight time3h 51m
Cheapest price$339
Rochester, New York to St. Louis Flights
Fastest flight time4h 06m
Cheapest price$306
Syracuse to St. Louis Flights
Fastest flight time4h 29m
Cheapest price$250
Buffalo to St. Louis Flights
Fastest flight time3h 55m
Cheapest price$263
Islip, New York to Chicago Flights
Fastest flight time8h 00m
Cheapest price$118
White Plains to St. Louis Flights
Fastest flight time4h 11m
Cheapest price$275

Similar New Windsor to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your New Windsor to Chicago route

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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Airports listed have a maximum distance of 78.5 mi from Chicago


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