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

Currently priced at $245, Allegiant Air will fly you from New Windsor to Chicago and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip.

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

Travelers seeking maximum savings on their New Windsor to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

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

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 Friday. 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 31 days early can save you up to 88% on average compared to booking a flight this week. If booking 31 days before your flight isn’t an option for you, users have found flights from New Windsor to Chicago for as little as $211 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 $359 for flights departing within the next 3 days.

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

September can be a great time to fly to Chicago from New Windsor with a flight ticket averaging about $226. Cheapflights users have found deals in the month of September for as cheap as $74. The most expensive prices can be found in the month of December.

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

It’s typically best to fly out from New Windsor to Chicago in the morning. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.

Most accurate provider : When it comes to deals on New Windsor-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on New Windsor-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 New Windsor-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 0 different airlines.

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

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

How can I find direct flights from Stewart to Chicago?

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

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

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

$91+ Flights from New Windsor to Chicago

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1. Tell us where you want to go

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Cheap flight deals from Stewart to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$234 (Mytrip)
One-way from	$91 (Mytrip)
Popular in	December
Cheapest in	September
Average price	$256

Provider with most accurate pricing for New Windsor Stewart-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for New Windsor Stewart-Chicago (CHI) flights.

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From New Windsor Stewart to Chicago (CHI)

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One-way flight from New Windsor Stewart to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).

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Average for round-trip flights in March 2025

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Find flight deals from Stewart to Chicago

Cheapest flights from Stewart to Chicago
Explore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Thu 5/85:53 pmSWF - ORD

1 stop19h 53mMultiple Airlines

Sun 5/114:35 pmORD - SWF

1 stop26h 14mMultiple Airlines

Deal found 3/25

$234

Thu 5/18:04 pmSWF - RFD

1 stop13h 04mAllegiant Air

Sun 5/410:26 amRFD - SWF

1 stop21h 45mAllegiant Air

Deal found 3/25

$245

Thu 6/1211:11 amSWF - MDW

2 stops27h 52mAllegiant Air

Sun 6/1511:45 amMDW - SWF

1 stop21h 46mAllegiant Air

Deal found 3/25

$342

Best flights from Stewart to Chicago
Discover carefully curated flight deals from Stewart to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 26, 2025.

Thu 5/85:53 pmSWF - ORD

1 stop19h 53mMultiple Airlines

Sun 5/114:35 pmORD - SWF

1 stop26h 14mMultiple Airlines

Deal found 3/25

$234

Thu 5/18:04 pmSWF - RFD

1 stop13h 04mAllegiant Air

Sun 5/410:26 amRFD - SWF

1 stop21h 45mAllegiant Air

Deal found 3/25

$245

Thu 6/1211:11 amSWF - MDW

2 stops27h 52mAllegiant Air

Sun 6/1511:45 amMDW - SWF

1 stop21h 46mAllegiant Air

Deal found 3/25

$342

Last-minute flights from Stewart to Chicago
Discover last-minute flight deals from Stewart to Chicago. Data last updated March 26, 2025 and is based on user searches.

Mon 3/3110:10 amSWF - ORD

2 stops28h 58mMultiple Airlines

Thu 4/35:10 amORD - SWF

1 stop27h 10mMultiple Airlines

Deal found 3/25

$360

Wed 4/910:51 amSWF - MDW

1 stop24h 27mAllegiant Air

Sun 4/1311:08 amMDW - SWF

1 stop29h 28mAllegiant Air

Deal found 3/25

$400

Fri 4/2511:50 amSWF - ORD

1 stop22h 34mMultiple Airlines

Sun 4/275:36 amORD - SWF

1 stop28h 24mMultiple Airlines

Deal found 3/25

$255

One-way flights from Stewart to Chicago
Search for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Data last updated March 26, 2025.

Mon 4/2811:50 amSWF - ORD

1 stop22h 34mMultiple Airlines

Deal found 3/25

$91

Mon 6/911:21 amSWF - RFD

1 stop24h 01mAllegiant Air

Deal found 3/25

$157

Sun 6/811:11 amSWF - MDW

2 stops33h 35mAllegiant Air

Deal found 3/25

$188

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/8

5:53 pm-12:46 pm

1 stop19h 53m

Chicago O'Hare Intl

Sun 5/11

4:35 pm-7:49 pm

1 stop26h 14m

$234

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 5/1

8:04 pm-8:08 am

1 stop13h 04m

Chicago Greater Rockford

Sun 5/4

10:26 am-9:11 am

1 stop21h 45m

$245

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 6/12

11:11 am-2:03 pm

2 stops27h 52m

Chicago Midway

Sun 6/15

11:45 am-10:31 am

1 stop21h 46m

$342

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/30

6:07 pm-12:42 pm

1 stop19h 35m

$103

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 6/9

11:21 am-10:22 am

1 stop24h 01m

$157

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 6/8

11:11 am-7:46 pm

2 stops33h 35m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Compare providers for flights from Stewart to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Chicago in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on New Windsor-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on New Windsor-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 New Windsor-Chicago 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 Stewart to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Stewart 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.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Chicago

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $323). 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.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Allegiant Air

7.3

Good

730 reviews

Reviews

1 / 20

10.0

Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Allegiant Air

7.3

Good

730 reviews

Allegiant Air

7.3

Good

730 reviews

Reviews

1 / 20

10.0

Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Related info for your journey

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 0 different airlines.
What is the cheapest airline to fly from New Windsor to Chicago round-trip?
Currently priced at $245, Allegiant Air will fly you from New Windsor to Chicago and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip.
What are the most popular routes from New Windsor to Chicago?
While some choose either New Windsor Stewart - Chicago Greater Rockford or New Windsor Stewart - Chicago Midway, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Chicago.
Can I find deals for flights from Stewart to Chicago that include hotel bookings?
Yes. In addition to deals on Stewart to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Chicago.
Can I find deals for business class flights from Stewart to Chicago?
Yes. Cheapflights offers flight deals from Stewart to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from New Windsor to Chicago?
Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $323). 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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$91+ Cheap flights from New Windsor (SWF) to Chicago (CHI)

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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Chicago

Cheapest flights from Stewart to ChicagoExplore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Explore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.

Compare providers for flights from Stewart to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Chicago in March.

Best time to book a flight from Stewart to Chicago

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

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Chicago

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Related info for your journey

Find useful and relevant information for your journey from Stewart to Chicago. 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 from for flights from New Windsor to Chicago?

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

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

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

How can I find direct flights from Stewart to Chicago?

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

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

Traveling to a place near New Windsor?

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Alternative routes for Stewart to Chicago

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Cheapest flights from Stewart to Chicago
Explore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.