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Cheap flights from Chicago (CHI) to New Windsor (SWF) from $111

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 10/16. 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
Jun 22 — Jun 291
From?
To?
Sat 6/22
Sat 6/29
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 June 17, 2024.

Round-trip from

$214

One-way from

$111
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 13%.

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 104% 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 $259. For sooner than that we have options available in the next 3 days from $364.

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 $220. You can even find prices in February for less than $220, as users have found deals to New Windsor from as low as $72. The month of July 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 17%.

What is the cheapest time of day to fly from CHI to SWF?

Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Chicago to New Windsor by exploring options for tickets in the morning.

Cheap Chicago to Stewart flights in June & July 2024

Find cheap flight options from Chicago to Stewart specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,263,674 searches. Prices were last updated on June 17, 2024.
Mon 7/17:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Fri 7/511:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/17$325
Fri 6/287:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Fri 7/511:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/17$335
Sun 7/147:18 amORD - SWF
1 stop7h 59mMultiple Airlines
Fri 7/1911:59 amSWF - ORD
1 stop7h 15mMultiple Airlines
Deal found 6/16$356
Sun 6/306:10 amORD - SWF
2 stops10h 17mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 6/16$362
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 6/16$370
Sun 6/306:10 amORD - SWF
2 stops10h 17mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
3 stops32h 34mMultiple Airlines
Deal found 6/16$374
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Mon 7/811:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/16$394
Sun 7/146:30 amORD - SWF
2 stops8h 47mMultiple Airlines
Fri 7/1911:59 amSWF - ORD
1 stop7h 15mMultiple Airlines
Deal found 6/16$395
Fri 7/199:33 pmORD - SWF
2 stops18h 54mMultiple Airlines
Sun 7/215:07 pmSWF - ORD
2 stops17h 07mMultiple Airlines
Deal found 6/16$413

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 3,263,674 searches. Data last updated June 17, 2024.
Mon 7/17:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Fri 7/511:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/17$325
Fri 6/287:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Fri 7/511:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/17$335
Sun 7/147:18 amORD - SWF
1 stop7h 59mMultiple Airlines
Fri 7/1911:59 amSWF - ORD
1 stop7h 15mMultiple Airlines
Deal found 6/16$356
Sun 6/306:10 amORD - SWF
2 stops10h 17mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 6/16$362
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 6/16$370
Sun 6/306:10 amORD - SWF
2 stops10h 17mMultiple Airlines
Mon 7/812:46 pmSWF - ORD
3 stops32h 34mMultiple Airlines
Deal found 6/16$374
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Mon 7/811:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 6/16$394
Sun 7/146:30 amORD - SWF
2 stops8h 47mMultiple Airlines
Fri 7/1911:59 amSWF - ORD
1 stop7h 15mMultiple Airlines
Deal found 6/16$395
Fri 7/199:33 pmORD - SWF
2 stops18h 54mMultiple Airlines
Sun 7/215:07 pmSWF - ORD
2 stops17h 07mMultiple Airlines
Deal found 6/16$413

Chicago to Stewart flights leaving soon

Find last-minute flight options from Chicago to Stewart for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,263,674 searches. Data last updated June 17, 2024.
Sat 6/227:18 amORD - SWF
1 stop9h 13mMultiple Airlines
Wed 6/267:13 pmSWF - ORD
3 stops24h 53mMultiple Airlines
Deal found 6/16$671
Sat 6/228:39 pmORD - SWF
2 stops19h 48mMultiple Airlines
Wed 6/267:13 pmSWF - ORD
3 stops24h 53mMultiple Airlines
Deal found 6/16$728
Sat 6/225:21 amORD - SWF
3 stops35h 06mMultiple Airlines
Wed 6/267:13 pmSWF - ORD
3 stops24h 53mMultiple Airlines
Deal found 6/16$763

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 3,263,674 searches. Data last updated June 17, 2024.
Wed 10/167:10 pmORD - SWF
1 stop14h 21mMultiple Airlines
Deal found 6/16$111
Wed 8/147:48 pmORD - SWF
1 stop12h 18mMultiple Airlines
Deal found 6/15$136
Sun 6/306:10 amORD - SWF
2 stops10h 17mMultiple Airlines
Deal found 6/16$141
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Deal found 6/16$149
Thu 7/48:27 amORD - SWF
1 stop6h 50mMultiple Airlines
Deal found 6/16$154
Thu 7/48:27 amORD - SWF
1 stop6h 50mMultiple Airlines
Deal found 6/16$155
Thu 7/187:18 amORD - SWF
1 stop7h 59mMultiple Airlines
Deal found 6/16$157
Sat 8/177:48 pmORD - SWF
1 stop12h 18mMultiple Airlines
Deal found 6/16$160
Mon 7/17:18 amORD - SWF
1 stop9h 47mMultiple Airlines
Deal found 6/16$161

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 3,263,674 searches. Data last updated June 17, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$325 - $413

Route

Depart

Return

Price

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 7/1

1 stop9h 47m

New Windsor Stewart

Fri 7/5

1 stop7h 13m

$325

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 7/11

1 stop7h 59m

New Windsor Stewart

Mon 7/15

1 stop7h 15m

$335

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 7/14

1 stop7h 59m

New Windsor Stewart

Fri 7/19

1 stop7h 15m

$356

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/30

2 stops10h 17m

New Windsor Stewart

Mon 7/8

2 stops20h 48m

$362

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/30

1 stop9h 09m

New Windsor Stewart

Mon 7/8

2 stops20h 48m

$370

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/30

2 stops10h 17m

New Windsor Stewart

Mon 7/8

3 stops32h 34m

$374

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/30

1 stop9h 09m

New Windsor Stewart

Mon 7/8

1 stop7h 13m

$394

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 7/14

2 stops8h 47m

New Windsor Stewart

Fri 7/19

1 stop7h 15m

$395

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 7/19

2 stops18h 54m

New Windsor Stewart

Sun 7/21

2 stops17h 07m

$413

Flights are sorted by cheapest first

Deals found on 6/17

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Stewart. Price data was last updated on June 16, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to New Windsor flight should consider departing on Friday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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 June 17, 2024.
Allegiant Air
7.5
Good
985 reviews

Boarding

7.7

Crew

8.2

Food

6.2

Overall

7.5

Entertainment

5.8

Comfort

6.9

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
985 reviews
Allegiant Air
7.5
Good
985 reviews

Boarding

7.7

Crew

8.2

Food

6.2

Overall

7.5

Entertainment

5.8

Comfort

6.9

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 $400 on Cheapflights?

    Yes, there are multiple flights from Chicago to New Windsor for under $400. The cheapest flight booked recently is on Multiple Airlines for just $325, but on average you can expect to pay $427.

  • Are there last-minute flights available from Chicago to New Windsor for under $700?

    There are currently 3+ open flights from Chicago to New Windsor within the next 7 days for less than $700.

  • 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 6/17.

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

    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 $185). 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.

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Alternative routes for Chicago to Stewart
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

Find flights from Chicago to Stewart, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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