SWF - CHI

$99 Find Cheap Flights from New Windsor to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Chicago departing on 8/18. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Chicago, 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 New Windsor to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from New Windsor to Chicago (SWF-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Chicago 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Chicago

Fri, Aug 22 - Sun, Aug 24
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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5:16 pm - 10:12 amORD-SWF
15h 56m1 stop
Mon, Aug 18 - Fri, Aug 22
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
Fri, Aug 22 - Sun, Aug 24
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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5:16 pm - 10:12 amORD-SWF
15h 56m1 stop
Fri, Aug 22 - Mon, Aug 25
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
Fri, Aug 22 - Sun, Aug 24
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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5:16 pm - 10:12 amORD-SWF
15h 56m1 stop
Fri, Aug 22 - Mon, Aug 25
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
Mon, Aug 25 - Thu, Aug 28
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
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10:12 am - 6:00 pmORD-SWF
6h 48m1 stop
Fri, Aug 15 - Mon, Aug 25
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
Fri, Aug 15 - Mon, Aug 18
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
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10:26 am - 6:47 pmORD-SWF
7h 21m1 stop
Fri, Aug 15 - Mon, Aug 25
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
Useful Info

Good to know

Cheapest flight$99
Flight from Stewart Intl. to Chicago O'Hare Airport

When to book flights from New Windsor to Chicago

Are your dates flexible? Find out the best times to travel from New Windsor to Chicago 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 Stewart Intl. to Chicago

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

    In the last 3 days, the lowest price for a flight from New Windsor to Chicago was $99 for a one-way ticket and $218 for a round-trip.

  • Do I need a passport to fly between Stewart Intl. and Chicago?

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

  • Which airports will I be using when flying from Stewart Intl. to Chicago?

    Stewart Intl. is served by only 1 airport and there are 2 airports in Chicago. You will leave Stewart Intl. from New Windsor Stewart and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    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 Stewart Intl. to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Stewart Intl. 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 Stewart Intl. to Chicago?

    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 Chicago with an airline and back to Stewart Intl. with another airline.

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

    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 Chicago from Stewart Intl. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from New Windsor to Chicago

 
See real verified KAYAK customer reviews for airlines flying from New Windsor to Chicago. 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 New Windsor to Chicago? 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.
6.3
Spirit AirlinesOverall score based on 8048 reviews
5.1Food
5.0Entertainment
6.6Boarding
7.0Crew
5.9Comfort
Airline reviews

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

4.0 OkayAnonymous, Jul 2025MCO - ORD
Read more Spirit Airlines reviews

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

Everything you need to know for your flight from New Windsor to Chicago

Information on your arrival and departure airports

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