Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to New Windsor from $90

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 1/15. 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
"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.

Cheap one-way flights

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

Find recent round-trip train or bus tickets from Chicago to New York.

All round-trip flight deals to New York

The cheapest plane tickets to New York found on KAYAK recently.
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
5:59 pm - 9:39 amSWF-ORD
16h 40m1 stop
Wed, Jan 15 - Wed, Jan 22
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
5:59 pm - 9:39 amSWF-ORD
16h 40m1 stop
Wed, Jan 15 - Sat, Jan 18
1:35 pm - 1:35 pmORD-SWF
23h 00m2 stops
2:25 pm - 11:32 pmSWF-ORD
10h 07m1 stop
Thu, Jan 23 - Mon, Jan 27
6:06 pm - 11:20 amORD-SWF
16h 14m2 stops
6:44 pm - 11:32 amSWF-ORD
17h 48m1 stop
Thu, Jan 9 - Sun, Jan 12
4:27 pm - 1:35 pmORD-SWF
20h 08m2 stops
2:25 pm - 4:10 pmSWF-ORD
26h 45m3 stops
Thu, Jan 23 - Mon, Jan 27
10:29 am - 11:20 amORD-SWF
23h 51m3 stops
2:25 pm - 11:32 pmSWF-ORD
10h 07m1 stop
Thu, Jan 23 - Mon, Jan 27
3:56 pm - 6:04 pmORD-SWF
25h 08m2 stops
5:59 pm - 9:39 amSWF-ORD
16h 40m1 stop
Wed, Jan 15 - Sat, Jan 18
4:27 pm - 6:04 pmORD-SWF
24h 37m3 stops
5:59 pm - 9:39 amSWF-ORD
16h 40m1 stop
Wed, Jan 15 - Sat, Jan 18
7:26 am - 11:20 amORD-SWF
26h 54m3 stops
2:25 pm - 4:10 pmSWF-ORD
26h 45m3 stops
Thu, Jan 23 - Mon, Jan 27
6:06 pm - 11:25 amORD-SWF
16h 19m2 stops
7:54 pm - 11:32 amSWF-ORD
16h 38m1 stop
Thu, Feb 6 - Sun, Feb 9
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
Wed, Jan 15
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
Wed, Jan 29
6:05 am - 5:19 pmORD-SWF
10h 14m1 stop
Wed, Jan 8
5:11 am - 1:35 pmORD-SWF
7h 24m1 stop
Fri, Jan 24
5:11 am - 1:35 pmORD-SWF
7h 24m1 stop
Fri, Jan 24
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
Sat, Jan 18
7:26 am - 6:48 pmORD-SWF
10h 22m1 stop
Thu, Jan 23
7:26 am - 6:48 pmORD-SWF
10h 22m1 stop
Thu, Jan 16
5:38 pm - 10:21 amMDW-SWF
15h 43m1 stop
$143Allegiant Air
Find Deal
Sun, Jan 5
6:36 pm - 10:01 amMDW-SWF
14h 25m1 stop
$146Allegiant Air
Find Deal
Tue, Apr 1
5:00 am - 5:37 pmORD-SWF
11h 37m1 stop
6:27 pm - 11:04 amSWF-ORD
17h 37m1 stop
$1,013
Find Deal
Mon, Dec 23 - Fri, Dec 27
9:47 am - 11:00 amORD-SWF
24h 13m2 stops
6:27 pm - 11:04 amSWF-ORD
17h 37m1 stop
$1,028
Find Deal
Mon, Dec 23 - Fri, Dec 27
9:47 am - 11:00 amORD-SWF
24h 13m2 stops
6:27 pm - 9:53 pmSWF-ORD
28h 26m2 stops
$1,045
Find Deal
Mon, Dec 23 - Fri, Dec 27
5:00 am - 11:00 amORD-SWF
29h 00m3 stops
6:27 pm - 9:53 pmSWF-ORD
28h 26m2 stops
$1,072
Find Deal
Mon, Dec 23 - Fri, Dec 27
8:14 pm - 11:06 amORD-SWF
13h 52m2 stops
11:46 am - 9:53 pmSWF-ORD
11h 07m2 stops
$1,078
Find Deal
Thu, Dec 19 - Mon, Dec 23
5:00 am - 11:00 amORD-SWF
29h 00m3 stops
6:27 pm - 12:33 amSWF-ORD
31h 06m3 stops
$1,139
Find Deal
Mon, Dec 23 - Fri, Dec 27
8:05 pm - 5:50 pmORD-SWF
20h 45m2 stops
11:46 am - 9:03 amSWF-ORD
22h 17m3 stops
$1,205
Find Deal
Sat, Dec 21 - Mon, Dec 23

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 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.

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

You could potentially save up to 38% 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

$90

Fastest flight time

7h 24m

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 $90. The best round-trip flight deal from Chicago to New Windsor found on momondo in the last 72 hours is $208.
The fastest flight from Chicago to New Windsor takes 7h 24m
There are no direct flights from Chicago to New Windsor. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - New Windsor Stewart Airport and Chicago Midway 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 10h 44m 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.


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.


An easier way to manage your New Windsor trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 12/23
Mon 12/30
Email me momondo's favorite deals

Find better results for your trip to the United States