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Cheap flights from Chicago to New Windsor from $111

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 12/11. 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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0 bags
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Find the cheapest flights from Chicago to New York

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to New York that have been recently found on momondo from popular airlines, departing in the coming months.

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Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to New York.

Cheap last minute flights

Planning a quick getaway from Chicago to New York? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to New York, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to New York

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All round-trip flight deals to New York

The cheapest plane tickets to New York found on KAYAK recently.
8:20 am - 6:50 pmORD-SWF
9h 30m1 stop
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
Wed, Dec 11 - Fri, Dec 13
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
2:10 pm - 11:02 pmSWF-ORD
9h 52m1 stop
Sat, Jan 11 - Mon, Jan 13
5:00 am - 5:37 pmORD-SWF
11h 37m1 stop
2:10 pm - 11:02 pmSWF-ORD
9h 52m1 stop
Mon, Jan 6 - Fri, Jan 10
4:27 pm - 1:20 pmORD-SWF
19h 53m2 stops
2:10 pm - 11:02 pmSWF-ORD
9h 52m1 stop
Thu, Jan 9 - Mon, Jan 13
6:06 pm - 11:20 amORD-SWF
16h 14m2 stops
6:44 pm - 11:12 amSWF-ORD
17h 28m1 stop
Thu, Jan 9 - Sun, Jan 12
4:27 pm - 6:04 pmORD-SWF
24h 37m2 stops
2:10 pm - 11:02 pmSWF-ORD
9h 52m1 stop
Sat, Jan 11 - Mon, Jan 13
6:06 pm - 11:20 amORD-SWF
16h 14m2 stops
6:44 pm - 11:12 amSWF-ORD
17h 28m1 stop
Thu, Jan 30 - Sun, Feb 2
9:58 am - 10:07 amORD-SWF
23h 09m2 stops
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
Sun, Dec 8 - Mon, Dec 9
5:11 pm - 12:05 pmORD-SWF
17h 54m1 stop
6:30 pm - 12:33 amSWF-ORD
31h 03m3 stops
Thu, Dec 12 - Sun, Dec 15
9:58 am - 10:07 amORD-SWF
23h 09m2 stops
12:55 pm - 5:40 pmSWF-ORD
29h 45m3 stops
Sun, Dec 8 - Mon, Dec 9
8:20 am - 6:50 pmORD-SWF
9h 30m1 stop
Wed, Dec 11
8:20 am - 6:50 pmORD-SWF
9h 30m1 stop
Sat, Dec 14
5:11 pm - 12:05 pmORD-SWF
17h 54m1 stop
Sun, Dec 15
5:25 am - 5:50 pmORD-SWF
11h 25m2 stops
Thu, Dec 5
7:20 am - 6:48 pmORD-SWF
10h 28m1 stop
Sun, Jan 19
7:45 pm - 10:07 amORD-SWF
13h 22m1 stop
Thu, Dec 12
5:00 am - 5:37 pmORD-SWF
11h 37m1 stop
Mon, Jan 6
7:20 am - 6:48 pmORD-SWF
10h 28m1 stop
Sun, Jan 26
6:06 pm - 11:20 amORD-SWF
16h 14m2 stops
Sun, Feb 2
5:38 pm - 10:11 amMDW-SWF
15h 33m1 stop
$336Allegiant Air
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Sun, Dec 29
5:41 pm - 11:00 amORD-SWF
16h 19m2 stops
6:35 pm - 10:56 amSWF-ORD
17h 21m1 stop
Mon, Nov 25 - Thu, Nov 28
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
6:30 pm - 2:31 pmSWF-ORD
21h 01m2 stops
Sun, Nov 24 - Tue, Nov 26
4:45 pm - 11:00 amORD-SWF
17h 15m2 stops
6:35 pm - 10:56 amSWF-ORD
17h 21m1 stop
Mon, Nov 25 - Thu, Nov 28
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
11:40 am - 8:15 pmSWF-ORD
9h 35m1 stop
Sun, Nov 24 - Tue, Nov 26
5:41 pm - 11:00 amORD-SWF
16h 19m2 stops
6:35 pm - 10:56 amSWF-ORD
17h 21m1 stop
Mon, Nov 25 - Thu, Nov 28
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
11:40 am - 2:31 pmSWF-ORD
27h 51m3 stops
Sun, Nov 24 - Tue, Nov 26
8:44 am - 1:10 pmORD-SWF
27h 26m3 stops
6:30 pm - 2:31 pmSWF-ORD
21h 01m2 stops
Sun, Nov 24 - Tue, Nov 26
8:44 am - 1:10 pmORD-SWF
27h 26m3 stops
11:40 am - 2:31 pmSWF-ORD
27h 51m3 stops
Sun, Nov 24 - Tue, Nov 26
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
10:10 am - 8:03 pmSWF-ORD
10h 53m1 stop
Sun, Nov 24 - Sun, Dec 1

See travel insights to New York from

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 Chicago for New Windsor?

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

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

In the afternoon. Chicago to New Windsor flights are approximately 3% more expensive in the morning than in the afternoon

What is the cheapest Chicago to New Windsor flight route?

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

Can stopping save me money on Chicago to New Windsor flights?

You could potentially save up to 11% on your flight if you consider stops on a Chicago to New Windsor flight.

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

$111

Fastest flight time

9h 20m

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 $111. The best round-trip flight deal from Chicago to New Windsor found on momondo in the last 72 hours is $217.
The fastest flight from Chicago to New Windsor takes 9h 20m
There are no direct flights from Chicago to New Windsor. Popular non-direct route for this connection is 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 9h 30m 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.

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


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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