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

CHI — SWF
May 22 — May 291

The best prices from Chicago to New Windsor Stewart are usually found in March or July, booked 44 days in advance, depart on a Wednesday or Monday and return on a Wednesday

How to find the cheapest flight from Chicago to Stewart

All the information you need to plan the best CHI to SWF flight in 2022: compare Chicago to Stewart flight prices with the expected peak season, weather and rainfall in Stewart.

CHI - SWF

Price

$146 - $370

Popular inNovemberHigh demand for flights, 30% potential price rise
Cheapest inMarchBest time to find cheap flights, 44% potential price drop
Round-trip from$146From Chicago (CHI) to New Windsor Stewart
One-way from$134One-way flight from Chicago (CHI) to New Windsor Stewart

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

Wednesday is generally a great day to depart. Flying on this day could help you save up to 28%.

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

The best pricing can be found in the month of August. Prices to New Windsor from Chicago average $168. You can even find prices in August for less than $168, as users have found deals to New Windsor from as low as $58. The month of December 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 31% on flights from Chicago to New Windsor by exploring options for tickets in the afternoon.

Cheap flights from Chicago to Stewart in May, June 2022

The best prices found for CHI to SWF flights for May, June
Jun 10 - Jun 15
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

16h 03m
$248

Multiple Airlines

View Deal

Deal found 5/14/22

Jun 17 - Jun 20
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

24h 06m
$257

Multiple Airlines

View Deal

Deal found 5/17/22

Jun 17 - Jun 20
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

24h 06m
$259

Multiple Airlines

View Deal

Deal found 5/17/22

Chicago to Stewart 2022 flight deals

Cheap flights to Stewart from Chicago found for this year
Jun 10 - Jun 15
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

16h 03m
$248

Multiple Airlines

View Deal

Deal found 5/14/22

Jun 17 - Jun 20
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

24h 06m
$257

Multiple Airlines

View Deal

Deal found 5/17/22

Jun 17 - Jun 20
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

22h 38m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

24h 06m
$259

Multiple Airlines

View Deal

Deal found 5/17/22

Cheap Allegiant Air flights from Chicago to Stewart

Aug 4 - Aug 11
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

13h 43m
SWF

New Windsor Stewart

MDW

Chicago Midway

2 stops

20h 48m
$306

Allegiant Air

View Deal

Deal found 5/15/22

Aug 4 - Aug 7
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

13h 43m
SWF

New Windsor Stewart

MDW

Chicago Midway

2 stops

20h 48m
$374

Allegiant Air

View Deal

Deal found 5/15/22

Jun 30 - Jul 7
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

13h 15m
SWF

New Windsor Stewart

MDW

Chicago Midway

2 stops

20h 51m
$385

Allegiant Air

View Deal

Deal found 5/15/22

Last minute flights from Chicago to Stewart

Late deals on return flights to Stewart from Chicago, departing today and this week
May 24 - May 26
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

8h 20m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

9h 21m
$270

Multiple Airlines

View Deal

Deal found 5/15/22

May 24 - May 28
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

8h 20m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

12h 03m
$323

Multiple Airlines

View Deal

Deal found 5/16/22

May 24 - Jun 2
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

8h 20m
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

9h 21m
$359

Multiple Airlines

View Deal

Deal found 5/16/22

One-way flights to New Windsor Stewart from Chicago

The cheapest one-way flights from Chicago to Stewart
May 24
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

15h 54m
$95

Frontier

View Deal

Deal found 5/14/22

Aug 14
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

13h 43m
$102

Allegiant Air

View Deal

Deal found 5/14/22

Jul 3
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

13h 09m
$107

Allegiant Air

View Deal

Deal found 5/15/22

Related info for your journey

Useful info, stats and facts about Chicago to Stewart flights.

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 2 different airlines.

Which airlines flying from Chicago to New Windsor Stewart have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to New Windsor Stewart that may be offering flexible cancellation policies are Delta and American Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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 $248, but on average you can expect to pay $277.

Are there last-minute flights available from Chicago to New Windsor for under $300?

There are currently 20+ open flights from Chicago to New Windsor within the next 7 days for less than $300.

What is the cheapest airline to fly from Chicago to New Windsor round-trip?

Cheapflights users have booked flights from Chicago to New Windsor round-trip from $306.

What are the cheapest flights from Chicago to New Windsor?

While on average a flight from Chicago to New Windsor is generally $146, our data shows the cheapest flight currently is $118. When looking at the most popular route, (Chicago O'Hare Intl - New Windsor Stewart), you can expect to pay $267 for that flight.

Alternative routes for Chicago to Stewart

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

Top airline flying from Chicago to Stewart

The chart below displays the airlines Cheapflights users traveling from Chicago to Stewart choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
DeltaCheapest$89Average$268FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
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