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

SWF — CHI
Aug 13 — Aug 201

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

Flights from New Windsor to Chicago are found to be more expensive on Sunday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

Users have found that booking a flight from New Windsor to Chicago at least 26 days early can save you up to 21% on average compared to booking a flight this week. If booking 26 days before your flight isn’t an option for you, users have found flights from New Windsor to Chicago for as little as $256 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $300 for flights departing within the next 3 days.

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

January can be a great time to fly to Chicago from New Windsor with a flight ticket averaging about $235. Cheapflights users have found deals in the month of January for as cheap as $117. The most expensive prices can be found in the month of August.

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

It’s typically best to fly out from New Windsor to Chicago at noon. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Stewart to Chicago in August, September 2022

The best prices found for SWF to CHI flights for August, September
Aug 23 - Aug 30
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

9h 08m
$123

Frontier

Pick Dates

Deal found 7/8/22

Sep 19 - Sep 27
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

26h 37m
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

27h 31m
$126

Multiple Airlines

Pick Dates

Deal found 7/8/22

Aug 23 - Aug 29
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

26h 20m
$132

Frontier

Pick Dates

Deal found 7/8/22

Stewart to Chicago 2022 flight deals

Cheap flights to Chicago from Stewart found for this year
Aug 23 - Aug 30
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

9h 08m
$123

Frontier

Pick Dates

Deal found 7/8/22

Sep 19 - Sep 27
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

26h 37m
ORD

Chicago O'Hare Intl

SWF

New Windsor Stewart

1 stop

27h 31m
$126

Multiple Airlines

Pick Dates

Deal found 7/8/22

Aug 23 - Aug 29
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

26h 20m
$132

Frontier

Pick Dates

Deal found 7/8/22

Cheap Frontier flights from Stewart to Chicago

Aug 23 - Aug 30
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

9h 08m
$123

Frontier

Pick Dates

Deal found 7/8/22

Aug 23 - Aug 29
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

26h 20m
$132

Frontier

Pick Dates

Deal found 7/8/22

Aug 23 - Sep 4
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

6h 01m
$149

Frontier

Pick Dates

Deal found 7/8/22

Last minute flights from Stewart to Chicago

Late deals on return flights to Chicago from Stewart, departing today and this week
Aug 16 - Aug 23
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

9h 08m
$176

Frontier

Pick Dates

Deal found 7/8/22

Aug 16 - Aug 24
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

27h 03m
$195

Frontier

Pick Dates

Deal found 7/8/22

Aug 16 - Aug 25
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
MDW

Chicago Midway

SWF

New Windsor Stewart

1 stop

9h 39m
$216

Frontier

Pick Dates

Deal found 7/8/22

One-way flights to Chicago from Stewart

The cheapest one-way flights from Stewart to Chicago
Aug 30
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

21h 46m
$51

Frontier

Pick Dates

Deal found 7/8/22

Aug 30
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

17h 32m
$52

Multiple Airlines

Pick Dates

Deal found 7/8/22

Sep 21
SWF

New Windsor Stewart

MDW

Chicago Midway

1 stop

15h 24m
$64

Frontier

Pick Dates

Deal found 8/8/22

Related info for your journey

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

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

Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to Chicago from New Windsor. Booking flights from Stewart (SWF) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.

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

Some of our airline partners flying from New Windsor Stewart to Chicago have new flexible policies in place due to COVID-19. Delta is one of the carriers where you may find flexible change policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

Can I find flights from New Windsor to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from New Windsor to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $123, but on average you can expect to pay $162.

Are there last-minute flights available from New Windsor to Chicago for under $200?

There are currently 20+ open flights from New Windsor to Chicago within the next 7 days for less than $200.

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

Currently priced at $123, Frontier will fly you from New Windsor to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Frontier is priced at 47% lower than the current average price of a flight leaving 3 months from now.

What are the most popular routes from New Windsor to Chicago?

While some choose either New Windsor Stewart - Chicago Midway or New Windsor Stewart - Chicago Greater Rockford, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Chicago.

What are the cheapest flights from New Windsor to Chicago?

On average you can expect to pay $474 for a flight from New Windsor to Chicago. The cheapest flight overall is $474 while the most popular route, (New Windsor Stewart - Chicago O'Hare Intl) is currently priced at $177.

Alternative routes for Stewart to Chicago

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

Top airline flying from Stewart to Chicago

The chart below displays the airlines Cheapflights users traveling from Stewart to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
DeltaCheapest$198Average$454FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights