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CHI - SWF

$99 Find cheap flights from Chicago to New Windsor

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to New Windsor departing on 7/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

Search hundreds of travel sites at once for deals on flights to Stewart Intl.

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New Windsor, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New Windsor, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to New Windsor (CHI-SWF)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to New Windsor that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:18 am - 6:05 pmORD-SWF
9h 47m1 stop
11:59 am - 6:12 pmSWF-ORD
7h 13m1 stop
Fri, Jun 28 - Fri, Jul 5
7:18 am - 4:17 pmORD-SWF
7h 59m1 stop
11:59 am - 6:14 pmSWF-ORD
7h 15m1 stop
Thu, Jul 18 - Mon, Jul 22
7:18 am - 4:17 pmORD-SWF
7h 59m1 stop
11:59 am - 6:14 pmSWF-ORD
7h 15m1 stop
Thu, Jul 25 - Mon, Jul 29
7:18 am - 5:27 pmORD-SWF
9h 09m1 stop
11:59 am - 6:14 pmSWF-ORD
7h 15m1 stop
Sat, Jul 6 - Fri, Jul 12
7:18 am - 5:27 pmORD-SWF
9h 09m1 stop
11:59 am - 9:14 amSWF-ORD
22h 15m2 stops
Sat, Jul 6 - Fri, Jul 12
5:20 am - 4:17 pmORD-SWF
9h 57m2 stops
11:59 am - 6:14 pmSWF-ORD
7h 15m1 stop
Thu, Jul 25 - Mon, Jul 29
7:18 am - 5:27 pmORD-SWF
9h 09m1 stop
11:59 am - 8:39 pmSWF-ORD
33h 40m3 stops
Sat, Jul 6 - Fri, Jul 12
8:39 pm - 4:17 pmORD-SWF
18h 38m2 stops
11:59 am - 8:39 pmSWF-ORD
33h 40m3 stops
Sat, Jul 6 - Fri, Jul 12
7:26 am - 5:58 pmORD-SWF
9h 32m1 stop
11:21 am - 12:00 amSWF-ORD
13h 39m2 stops
Sun, Oct 6 - Sun, Oct 13
7:26 am - 5:58 pmORD-SWF
9h 32m1 stop
11:21 am - 12:00 amSWF-ORD
13h 39m2 stops
Sun, Oct 6 - Sun, Oct 13

Good to know

Cheapest flight

$99
Flight from Chicago O'Hare Airport to New Windsor

When to book flights from Chicago to New Windsor

Are your dates flexible? Find out the best times to travel from Chicago to New Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Stewart Intl.

  • What is the cheapest flight from Chicago to New Windsor?

    In the last 3 days, the lowest price for a flight from Chicago to New Windsor was $99 for a one-way ticket and $294 for a round-trip.

  • Do I need a passport to fly between Chicago and New Windsor?

    No, a passport isn't needed to fly from Chicago to New Windsor. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to New Windsor?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. New Windsor Stewart is the only airport in New Windsor. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.

  • Which aircraft models fly most regularly from Chicago to Stewart Intl.?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago to Stewart Intl.?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Stewart Intl..

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Stewart Intl.?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Stewart Intl.?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Stewart Intl.?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Chicago to New Windsor

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New Windsor. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to New Windsor? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.4
Spirit AirlinesOverall score based on 8616 reviews
5.3Food
5.1Entertainment
6.7Boarding
7.1Crew
5.9Comfort
Airline reviews

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

2.0 MediocreAnonymous, May 2024ORD - FLL
Read more about Spirit Airlines reviews

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

They didn’t let me get my boarding pass through the app because I have a lap infant. The ticket said to see a gate agent but there was no gate agent available. I was supposed to go to the kiosk. Ended up missing my flight and they said that I never checked in to my flight so there was nothing that could be done. I will never fly spirit again. Not even worth the hassle and poor customer service.

I like strict carry on policy. Quick to board, quick to leave. Less time at gate and get there quicker

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

comfortable flight. not fond of the idea to pay for every little detail. baggage checkin or carry ons, basic snack, or some sort of basic entertainment/wifi. would be nice to offer these as perks and stop with the penny pinching.

Flight was delayed 2+ hours missed a concert because of it…

Book cheap flights from Chicago to Stewart Intl.

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to New Windsor found on KAYAK in the last 72 hours.
7/23Tue
1 stop
13h 56mORD-SWF
$99
7/16Tue
1 stop
13h 56mORD-SWF
$118
6/22Sat
1 stop
9h 13mORD-SWF
$131
6/22Sat
1 stop
9h 13mORD-SWF
$132
6/5Wed
2 stops
16h 13mORD-SWF
$133
7/1Mon
1 stop
9h 47mORD-SWF
$144
6/21Fri
1 stop
9h 47mORD-SWF
$149
7/1Mon
1 stop
9h 47mORD-SWF
$151
6/23Sun
1 stopAllegiant Air
15h 47mMDW-SWF
$181
6/27Thu
1 stopAllegiant Air
23h 29mMDW-SWF
$259

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Flights to Stewart Intl.

Destination:

Stewart Intl. (SWF)United States

Return flight deals:

Stewart Intl. - Chicago

Cabin classes: