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Stewart

Cheap flights from Chicago (CHI) to New Windsor (SWF)

CHI — SWF
Nov 8 — Nov 151
Sun 11/8
Sun 11/15
1 adult, Economy
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Find cheap flights from Chicago to Stewart with Cheapflights

1. Tell us where you want to go

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Find flight deals from Chicago to Stewart

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Popular in

June

Cheapest in

January

Average price

$272
Provider with most accurate pricing for Chicago (CHI)-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New Windsor Stewart flights.
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Highest demand for flights based on searches. 12% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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  • Most accurate provider: When it comes to deals on Chicago-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-New Windsor flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Chicago with our price prediction graph.
Estimated round-trip price

Related info for your journey

  • What airport do you fly into for flights to New Windsor from Chicago?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to New Windsor from Chicago. Booking flights from Chicago to Stewart (SWF) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • Can I find deals for flights from Chicago to Stewart that include hotel bookings?

    Yes. In addition to deals on Chicago to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Stewart.

  • Can I find deals for business class flights from Chicago to Stewart?

    Yes. Cheapflights offers flight deals from Chicago to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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