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

Currently priced at $268, 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 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 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 36 days early can save you up to 89% on average compared to booking a flight this week. If booking 36 days before your flight isn’t an option for you, users have found flights from New Windsor to Chicago for as little as $227 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 $367 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 $228. Cheapflights users have found deals in the month of September for as cheap as $75. 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.

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.

$102+ Flights from New Windsor to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Stewart to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Stewart to Chicago

Round-trip from	$234 (Mytrip)
One-way from	$102 (Mytrip)
Popular in	December
Cheapest in	September
Average price	$268

From New Windsor Stewart to Chicago (CHI)

Search Deals

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

Search Deals

Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 2025

Search Deals

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 June 12, 2025.

Fri 7/257:56 pmSWF - ORD

1 stop28h 57mMultiple Airlines

Mon 7/285:05 amORD - SWF

1 stop13h 01mMultiple Airlines

Deal found 6/11

$234

Fri 10/108:21 pmSWF - RFD

1 stop21h 41mAllegiant Air

Mon 10/1310:44 amRFD - SWF

1 stop22h 42mAllegiant Air

Deal found 6/11

$268

Wed 7/211:50 amSWF - RFD

2 stops21h 41mMultiple Airlines

Fri 7/48:04 pmRFD - SWF

1 stop15h 14mMultiple Airlines

Deal found 6/12

$293

Thu 7/2411:13 amSWF - MDW

2 stops27h 51mAllegiant Air

Sun 7/2711:37 amMDW - SWF

1 stop21h 52mAllegiant Air

Deal found 6/10

$401

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11

$574

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 June 12, 2025.

Fri 7/257:56 pmSWF - ORD

1 stop28h 57mMultiple Airlines

Mon 7/285:05 amORD - SWF

1 stop13h 01mMultiple Airlines

Deal found 6/11

$234

Fri 10/108:21 pmSWF - RFD

1 stop21h 41mAllegiant Air

Mon 10/1310:44 amRFD - SWF

1 stop22h 42mAllegiant Air

Deal found 6/11

$268

Wed 7/211:50 amSWF - RFD

2 stops21h 41mMultiple Airlines

Fri 7/48:04 pmRFD - SWF

1 stop15h 14mMultiple Airlines

Deal found 6/12

$293

Thu 7/2411:13 amSWF - MDW

2 stops27h 51mAllegiant Air

Sun 7/2711:37 amMDW - SWF

1 stop21h 52mAllegiant Air

Deal found 6/10

$401

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11

$574

Last-minute flights from Stewart to Chicago
Discover last-minute flight deals from Stewart to Chicago. Data last updated June 12, 2025 and is based on user searches.

Wed 6/1811:31 amSWF - RFD

1 stop6h 37mAllegiant Air

Sun 6/2210:42 amRFD - SWF

1 stop22h 49mAllegiant Air

Deal found 6/10

$464

Wed 6/1811:31 amSWF - RFD

1 stop6h 37mMultiple Airlines

Sun 6/229:21 amRFD - SWF

2 stops32h 50mMultiple Airlines

Deal found 6/10

$518

Thu 6/1911:11 amSWF - MDW

2 stops27h 52mAllegiant Air

Sun 6/2211:45 amMDW - SWF

1 stop21h 46mAllegiant Air

Deal found 6/11

$623

Fri 6/208:01 pmSWF - ORD

1 stop13h 49mMultiple Airlines

Thu 6/2610:43 amORD - SWF

2 stops31h 28mMultiple Airlines

Deal found 6/10

$305

Wed 7/211:50 amSWF - RFD

2 stops21h 41mMultiple Airlines

Fri 7/48:04 pmRFD - SWF

1 stop15h 14mMultiple Airlines

Deal found 6/12

$293

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11

$574

Mon 7/2111:19 amSWF - RFD

1 stop24h 02mAllegiant Air

Thu 7/2410:41 amRFD - SWF

1 stop22h 48mAllegiant Air

Deal found 6/11

$301

Thu 7/2411:13 amSWF - MDW

2 stops27h 51mAllegiant Air

Sun 7/2711:37 amMDW - SWF

1 stop21h 52mAllegiant Air

Deal found 6/10

$401

Fri 7/257:56 pmSWF - ORD

1 stop28h 57mMultiple Airlines

Mon 7/285:05 amORD - SWF

1 stop13h 01mMultiple Airlines

Deal found 6/11

$234

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 June 12, 2025.

Thu 9/117:12 pmSWF - RFD

1 stop13h 48mAllegiant Air

Deal found 6/10

$102

Mon 7/217:56 pmSWF - ORD

1 stop13h 59mMultiple Airlines

Deal found 6/11

$112

Wed 7/211:50 amSWF - RFD

2 stops21h 41mMultiple Airlines

Deal found 6/10

$159

Sun 7/2711:13 amSWF - MDW

2 stops23h 28mAllegiant Air

Deal found 6/11

$195

Sun 6/297:52 pmSWF - MDW

2 stops19h 11mMultiple Airlines

Deal found 6/10

$353

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

Fri 7/25

7:56 pm-11:53 pm

1 stop28h 57m

Chicago O'Hare Intl

Mon 7/28

5:05 am-7:06 pm

1 stop13h 01m

$234

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 10/10

8:21 pm-5:02 pm

1 stop21h 41m

Chicago Greater Rockford

Mon 10/13

10:44 am-10:26 am

1 stop22h 42m

$268

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Wed 7/2

11:50 am-8:31 am

2 stops21h 41m

Chicago Greater Rockford

Fri 7/4

8:04 pm-12:18 pm

1 stop15h 14m

$293

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 7/24

11:13 am-2:04 pm

2 stops27h 51m

Chicago Midway

Sun 7/27

11:37 am-10:29 am

1 stop21h 52m

$401

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 7/3

7:52 pm-2:04 pm

2 stops19h 12m

Chicago Midway

Sun 7/6

11:37 am-10:29 am

1 stop21h 52m

$574

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 9/11

7:12 pm-8:00 am

1 stop13h 48m

$102

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 7/21

7:56 pm-8:55 am

1 stop13h 59m

$112

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Wed 7/2

11:50 am-8:31 am

2 stops21h 41m

$159

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 7/27

11:13 am-9:41 am

2 stops23h 28m

$195

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 6/29

7:52 pm-2:03 pm

2 stops19h 11m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 $321). 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

725 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

725 reviews

Allegiant Air

7.3

Good

725 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 $268, 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 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.
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 $321). 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.

See more FAQs

Merrillville

Lansing

Benton Harbor

Porter

Hammond

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$102+ 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 9/11. 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

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 June 12, 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 June 12, 2025.

Cheapflights Fare Finder

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

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Chicago

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

100% Free

Book with Flexibility

Travel Smart

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 June 12, 2025.