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CHI - SWF

Find cheap flights from Chicago to Stewart Intl. from $148

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 6/1. 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 5/25
Sat 6/1

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 44,979,812 times on KAYAK, and here is why:

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Good to know

Cheapest flight

$148
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 $148 for a one-way ticket.

  • 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 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 8756 reviews
5.3food
5.9comfort
5.2entertainment
6.8boarding
7.2crew
Airline reviews

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.

2.0 MediocreAnonymous, Mar 2024DTW - LGA
Read more about Spirit Airlines reviews

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…

The seats were larger & more roomy than the old planes. the crew was excellent. . overall a very good flight.

No water for handwashing and they charged $5 for water. Spirit up-charges for every little thing and the planes themselves are old and nauseating.

Seats could use more padding. Kind of hard on the tush.

Flying with Spirit is simple- it’s a minimalist airline that gets you from Point A to Point B. I have flown Spirit many times & have never had a problem with it, just don’t expect luxury or convenience. And know that, because the tickets are so affordable, the real charge comes in the bags, food, & extra purchases. The planes are simple, modern, and clean. They function in a way that moves large amounts of people in a more efficient manner, so the seats aren’t the most comfortable but I always bring a pillow and have no problem. I will continue to fly Spirit & would recommend to others

Comfortable experience but the boarding process was not efficient and the delay in departure caused some anxieties for the connecting flight. Flight from FLL to LGA was on time but the legroom for a taller person was a bit uncomfortable

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.
6/1Sat
1 stop
13h 38mORD-SWF
$148
6/5Wed
2 stops
21h 44mORD-SWF
$149
5/19Sun
2 stops
24h 08mORD-SWF
$155
6/5Wed
1 stop
14h 29mORD-SWF
$158
6/5Wed
3 stops
21h 44mORD-SWF
$162
5/19Sun
2 stops
24h 08mORD-SWF
$165
5/2Thu
2 stops
24h 28mORD-SWF
$198
5/2Thu
2 stops
30h 06mORD-SWF
$200
5/2Thu
3 stops
27h 26mORD-SWF
$208
5/1Wed
1 stop
14h 55mORD-SWF
$210

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Flights to Stewart Intl.

Destination:

Stewart Intl. (SWF)United States

Return flight deals:

Stewart Intl. - Chicago

Cabin classes: