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Cheap flights from Chicago (CHI) to New Windsor (SWF) from $109

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight 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.
CHI — SWF
May 10 — May 171
From?
To?
Fri 5/10
Fri 5/17
1 adult, Economy
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Cheap flight deals from Chicago to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 5, 2024.

Round-trip from

$214

One-way from

$109
From Chicago (CHI) to New Windsor Stewart
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One-way flight from Chicago (CHI) to New Windsor Stewart
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What is the cheapest day to fly round-trip from Chicago to New Windsor?

Monday is generally a great day to depart. Flying on this day could help you save up to 35%.

How far in advance should I book a flight from Chicago to New Windsor?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 54 days in advance, which can save you up to 123% on flights from Chicago to New Windsor compared to booking the week you need them. Waiting 54 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $276. For sooner than that we have options available in the next 3 days from $368.

What is the cheapest month to fly from Chicago to New Windsor?

The best pricing can be found in the month of February. Prices to New Windsor from Chicago average $228. You can even find prices in February for less than $228, as users have found deals to New Windsor from as low as $74. The month of June appears to be one of the more expensive times to travel to New Windsor from Chicago. Flying in the targeted month can save you up to 30%.

When is the cheapest time to fly from Chicago to New Windsor (CHI - SWF)?

Unlike in the morning, when flights are generally more expensive, you can save up to 9% on flights from Chicago to New Windsor by exploring options for tickets at noon.

Cheap Chicago to Stewart flights in May & June 2024

Find cheap flight options from Chicago to Stewart specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Prices were last updated on May 5, 2024.
Sat 5/186:40 pmORD - SWF
2 stops14h 05mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
3 stops28h 49mMultiple Airlines
Deal found 5/4$292
Sat 5/187:07 pmORD - SWF
1 stop13h 38mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
3 stops28h 49mMultiple Airlines
Deal found 5/4$296
Mon 6/37:30 amORD - SWF
1 stop9h 23mMultiple Airlines
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 5/4$327
Sat 5/187:07 pmORD - SWF
1 stop13h 38mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
2 stops20h 56mMultiple Airlines
Deal found 5/4$328
Mon 6/37:30 amORD - SWF
1 stop9h 23mMultiple Airlines
Mon 6/1012:46 pmSWF - ORD
3 stops28h 42mMultiple Airlines
Deal found 5/4$348
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/236:17 pmSWF - ORD
3 stops31h 38mMultiple Airlines
Deal found 5/4$409
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/2310:25 amSWF - ORD
2 stops11h 22mMultiple Airlines
Deal found 5/4$414
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/2310:25 amSWF - ORD
1 stop9h 40mMultiple Airlines
Deal found 5/4$424
Fri 6/219:10 pmORD - SWF
2 stops19h 21mMultiple Airlines
Sun 6/236:17 pmSWF - ORD
3 stops31h 38mMultiple Airlines
Deal found 5/4$426

Chicago to Stewart 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Stewart in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 5, 2024.
Sat 5/186:40 pmORD - SWF
2 stops14h 05mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
3 stops28h 49mMultiple Airlines
Deal found 5/4$292
Sat 5/187:07 pmORD - SWF
1 stop13h 38mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
3 stops28h 49mMultiple Airlines
Deal found 5/4$296
Mon 6/37:30 amORD - SWF
1 stop9h 23mMultiple Airlines
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 5/4$327
Sat 5/187:07 pmORD - SWF
1 stop13h 38mMultiple Airlines
Mon 5/2012:46 pmSWF - ORD
2 stops20h 56mMultiple Airlines
Deal found 5/4$328
Mon 6/37:30 amORD - SWF
1 stop9h 23mMultiple Airlines
Mon 6/1012:46 pmSWF - ORD
3 stops28h 42mMultiple Airlines
Deal found 5/4$348
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/236:17 pmSWF - ORD
3 stops31h 38mMultiple Airlines
Deal found 5/4$409
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/2310:25 amSWF - ORD
2 stops11h 22mMultiple Airlines
Deal found 5/4$414
Fri 6/217:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Sun 6/2310:25 amSWF - ORD
1 stop9h 40mMultiple Airlines
Deal found 5/4$424
Fri 6/219:10 pmORD - SWF
2 stops19h 21mMultiple Airlines
Sun 6/236:17 pmSWF - ORD
3 stops31h 38mMultiple Airlines
Deal found 5/4$426

One-way flights to Stewart from Chicago

Search for one-way flight options from Chicago to Stewart. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 5, 2024.
Tue 7/235:36 pmORD - SWF
1 stop14h 02mMultiple Airlines
Deal found 5/4$109
Sat 5/187:13 pmORD - SWF
2 stops13h 32mMultiple Airlines
Deal found 5/4$118
Sat 5/187:07 pmORD - SWF
1 stop13h 38mMultiple Airlines
Deal found 5/4$122
Sat 5/187:13 pmORD - SWF
2 stops13h 32mMultiple Airlines
Deal found 5/5$139
Sun 6/26:40 pmORD - SWF
2 stops14h 08mMultiple Airlines
Deal found 5/4$144
Sat 6/227:18 amORD - SWF
1 stop9h 13mMultiple Airlines
Deal found 5/5$159
Sat 6/227:18 amORD - SWF
1 stop9h 13mMultiple Airlines
Deal found 5/5$160
Sat 6/227:18 amORD - SWF
1 stop9h 13mMultiple Airlines
Deal found 5/5$161
Sun 5/1910:58 amORD - SWF
2 stops24h 08mMultiple Airlines
Deal found 5/4$171

Find flights from Chicago to Stewart within your budget

Customize your flight search to find flights from Chicago to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$292 - $426

Route

Depart

Return

Price

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 5/18

2 stops14h 05m

New Windsor Stewart

Mon 5/20

3 stops28h 49m

$292

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 5/18

1 stop13h 38m

New Windsor Stewart

Mon 5/20

3 stops28h 49m

$296

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 6/3

1 stop9h 23m

New Windsor Stewart

Mon 6/10

2 stops20h 48m

$327

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 5/18

1 stop13h 38m

New Windsor Stewart

Mon 5/20

2 stops20h 56m

$328

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 6/3

1 stop9h 23m

New Windsor Stewart

Mon 6/10

3 stops28h 42m

$348

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 6/21

1 stop9h 47m

New Windsor Stewart

Sun 6/23

3 stops31h 38m

$409

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 6/21

1 stop9h 47m

New Windsor Stewart

Sun 6/23

2 stops11h 22m

$414

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 6/21

1 stop9h 47m

New Windsor Stewart

Sun 6/23

1 stop9h 40m

$424

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 6/21

2 stops19h 21m

New Windsor Stewart

Sun 6/23

3 stops31h 38m

$426

Flights are sorted by cheapest first

Deals found on 5/4

No data available for this route at this time. Please check back soon.

Average price of flights to Stewart by month

Plan your trip from Chicago to Stewart by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Stewart is currently $143 while a round-trip flight costs $363. Price data was last updated on April 28, 2024.

Currently, January is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $125). Flying from Chicago to New Windsor in July is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$125

February

$149

March

$163

April

$157

May

$147

June

$173

July

$188

August

$158

September

$148

October

$165

November

$136

December

$170

Temperature and rainfall in Stewart by month

Plan your trip to Stewart by taking into account the average temperature and rainfall totals by month.

NYC

Temperature

33.8 - 77 °F

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated May 5, 2024.
Allegiant Air
7.5
Good
1,025 reviews
Check prices

Crew

8.2

Comfort

6.9

Entertainment

5.9

Overall

7.5

Boarding

7.7

Food

6.2

Reviews

1 / 10

Delayed because of crew missing stuck on tarmac at arrival for a full hour this delayed my trip 8 hours this caused me to miss my rental car they were closed for the day when I got there worst flight experience of my life

Allegiant Air
7.5
Good
1,025 reviews
Allegiant Air
7.5
Good
1,025 reviews
Check prices

Crew

8.2

Comfort

6.9

Entertainment

5.9

Overall

7.5

Boarding

7.7

Food

6.2

Reviews

1 / 10

Delayed because of crew missing stuck on tarmac at arrival for a full hour this delayed my trip 8 hours this caused me to miss my rental car they were closed for the day when I got there worst flight experience of my life

Related info for your journey

Find useful and relevant information for your journey from Chicago to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 flights from Chicago to New Windsor for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to New Windsor for under $300. The cheapest flight booked recently is on Multiple Airlines for just $292, but on average you can expect to pay $399.

  • What does ORD to SWF mean?

    ORD and SWF are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to SWF refers to a flight route from Chicago O'Hare Intl Airport to New Windsor Stewart Airport. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Stewart that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Stewart flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Stewart with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Stewart flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by 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.

  • Can I find deals for flights from Chicago to Stewart that allow pets onboard?

    Many airlines flying from Chicago to Stewart offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Stewart?

    Yes, you can often find last-minute deals on Chicago to Stewart flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to New Windsor flight deals updated?

    The Chicago to New Windsor flight deals you see on this page were last updated on 5/4.

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See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from Chicago to Stewart by cabin class

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Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Stewart?

When you search for this flight from Chicago to Stewart, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Stewart?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Chicago to Stewart for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Chicago to Stewart with no change fees?

Need flexible booking options for your flight to Stewart from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Stewart become cheaper?

Yes! Start tracking prices for Chicago to Stewart flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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