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Cheap flights from Chicago to New Windsor from $117

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to New Windsor departing on 5/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to New York

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to New York.
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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5:53 pm - 12:46 pmSWF-ORD
19h 53m1 stop
Sun, May 4 - Thu, May 8
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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5:53 pm - 12:46 pmSWF-ORD
19h 53m1 stop
Thu, May 1 - Thu, May 8
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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5:53 pm - 12:05 amSWF-ORD
31h 12m2 stops
Sun, May 4 - Thu, May 8
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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11:50 am - 9:24 amSWF-ORD
22h 34m1 stop
Thu, Apr 24 - Mon, Apr 28
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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11:50 am - 9:24 amSWF-ORD
22h 34m1 stop
Thu, Apr 24 - Mon, Apr 28
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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11:50 am - 9:24 amSWF-ORD
22h 34m1 stop
Thu, Apr 24 - Mon, Apr 28
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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11:50 am - 9:24 amSWF-ORD
22h 34m1 stop
Thu, Apr 24 - Mon, Apr 28
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9:09 am - 11:00 amORD-SWF
24h 51m2 stops
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5:53 pm - 12:46 pmSWF-ORD
19h 53m1 stop
Sun, May 4 - Thu, May 8
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7:33 pm - 11:00 amORD-SWF
14h 27m1 stop
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5:53 pm - 12:46 pmSWF-ORD
19h 53m1 stop
Sun, May 4 - Thu, May 8
Allegiant Air Logo
11:03 am - 12:25 pmMDW-SWF
24h 22m1 stop
Allegiant Air Logo
11:11 am - 7:46 pmSWF-MDW
33h 35m2 stops
$367Allegiant Air
Find Deal
Sun, Jun 1 - Sun, Jun 8

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How to get the cheapest flight ticket from Chicago to New Windsor

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 New Windsor?

On average, the least expensive day to fly to New Windsor from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $119. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to New Windsor on a Friday will generally be more expensive and average around $287. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to New Windsor?

According to our data, the cheapest time of day to fly to New Windsor is in the afternoon. momondo users have found flights departing from Chicago to New Windsor in the afternoon for as low as $170. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to New Windsor are more costly in the morning, with an average ticket price of $180. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to New Windsor according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to New Windsor (CHI to SWF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to New Windsor

Best Price Found

$117

Fastest flight time

8h 06m

Direct flights

None

Airports in New Windsor

1 airport
The best one-way flight to New Windsor from Chicago in the past 72 hours is $117. The best round-trip flight deal from Chicago to New Windsor found on momondo in the last 72 hours is $239.
The fastest flight from Chicago to New Windsor takes 8h 06m
There are no direct flights from Chicago to New Windsor. Popular non-direct routes for this connection are Chicago Midway Airport - New Windsor Stewart Airport and Chicago O'Hare Intl Airport - New Windsor Stewart Airport.
There is 1 airport near New Windsor: New Windsor Stewart (SWF)

  • How far is Chicago to New Windsor Stewart by plane?

    There are 701.4 mi between Chicago and New Windsor Stewart. Typically, this will take 12h 23m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to New Windsor Stewart Airport?

    Prices for flights from Chicago to New Windsor Stewart Airport were last updated today.

  • How old do you have to be to fly from Chicago to New Windsor Stewart Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The travel and health documents required for your trip to New Windsor Stewart Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New Windsor Stewart Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


Traveling to a place near New York?

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to New Windsor?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to New Windsor for you.

Can I find flights from Chicago to New Windsor with flexible booking policies on momondo?

All flight searches from Chicago to New Windsor on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to New Windsor?

momondo provides multiple filters to help you find the best flight to New Windsor from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to New Windsor right now. Can momondo alert me if prices change?

Price alerts on flights to New Windsor from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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