In terms of precipitation, rainfall in Chicago O'Hare Intl Airport 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 O'Hare Intl Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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).

How far in advance should I book a flight from New Windsor to Chicago O'Hare Intl Airport?

Find a great deal and save up to 93% by booking at least 36 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Chicago O'Hare Intl Airport within the next two weeks, with the cheapest ticket starting at $234.

What is the cheapest month to fly from New Windsor to Chicago O'Hare Intl Airport?

The best pricing can be found in the month of September. Prices to Chicago O'Hare Intl Airport from New Windsor average $232. You can even find prices in September for less than $232, as users have found deals to Chicago O'Hare Intl Airport from as low as $75. The month of June appears to be one of the more expensive times to travel to Chicago O'Hare Intl Airport from New Windsor. Flying in the targeted month can save you up to 19%.

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

When flying from New Windsor to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What airport do you fly from for flights from New Windsor to Chicago O'Hare Intl?

New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Chicago O'Hare Intl. You should not have trouble finding flights to Chicago O'Hare Intl from Stewart; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the New Windsor airport to Chicago O'Hare Intl. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.

Can I find deals for flights from Stewart to O'Hare Intl that include hotel bookings?

Yes. In addition to deals on Stewart to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Stewart to O'Hare Intl?

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

Can I find deals for business class flights from Stewart to O'Hare Intl?

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

$94+ Flights from New Windsor to Chicago O'Hare Intl Airport

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

Find cheap flights from Stewart to O'Hare Intl 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 O'Hare Intl

Round-trip from	$225 (Mytrip)
One-way from	$94 (Mytrip)
Popular in	June
Cheapest in	September
Average price	$267

From New Windsor Stewart to Chicago O'Hare Intl

Search Deals

One-way flight from New Windsor Stewart to Chicago O'Hare Intl

Search Deals

Highest demand for flights based on searches. 12% potential increase in price ($32 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in July 2025

Search Deals

Find flight deals from Stewart to O'Hare Intl

Cheapest flights from Stewart to O'Hare Intl
Explore the most affordable flight options available from Stewart to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

Fri 8/225:36 pmSWF - ORD

1 stop17h 55mMultiple Airlines

Sun 8/245:16 pmORD - SWF

1 stop15h 56mMultiple Airlines

Deal found 7/26

$225

Best flights from Stewart to O'Hare Intl
Discover carefully curated flight deals from Stewart to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 28, 2025.

Fri 8/225:36 pmSWF - ORD

1 stop17h 55mMultiple Airlines

Sun 8/245:16 pmORD - SWF

1 stop15h 56mMultiple Airlines

Deal found 7/26

$225

Last-minute flights from Stewart to O'Hare Intl
Discover last-minute flight deals from Stewart to O'Hare Intl. Data last updated July 28, 2025 and is based on user searches.

Mon 8/47:56 pmSWF - ORD

2 stops20h 35mMultiple Airlines

Mon 8/115:05 amORD - SWF

1 stop13h 01mMultiple Airlines

Deal found 7/25

$341

Fri 8/225:36 pmSWF - ORD

1 stop17h 55mMultiple Airlines

Sun 8/245:16 pmORD - SWF

1 stop15h 56mMultiple Airlines

Deal found 7/26

$225

One-way flights from Stewart to O'Hare Intl
Search for one-way flight options from Stewart to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated July 28, 2025.

Mon 8/187:37 pmSWF - ORD

1 stop15h 54mMultiple Airlines

Deal found 7/26

$94

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 8/22

5:36 pm-10:31 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

$225

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Best time to book a flight from Stewart to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

What is the cheapest month to book a flight from New Windsor to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $245). Flying from New Windsor to Chicago O'Hare Intl Airport 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.

Related info for your journey

What airport do you fly from for flights from New Windsor to Chicago O'Hare Intl?
New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Chicago O'Hare Intl. You should not have trouble finding flights to Chicago O'Hare Intl from Stewart; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the New Windsor airport to Chicago O'Hare Intl. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.
Can I find deals for flights from Stewart to O'Hare Intl that include hotel bookings?
Yes. In addition to deals on Stewart to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to O'Hare Intl?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to O'Hare Intl.
Can I find deals for business class flights from Stewart to O'Hare Intl?
Yes. Cheapflights offers flight deals from Stewart to O'Hare Intl 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 O'Hare Intl Airport?
Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $245). Flying from New Windsor to Chicago O'Hare Intl Airport 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

Schaumburg

Rosemont

Beloit

Hoffman Estates

Skokie

Naperville

Arlington Heights

Des Plaines

Elgin

Orland Park

Elk Grove Village

Racine

Rockford

Tinley Park

Merrillville

Evanston

Lake Geneva

Gurnee

Joliet

Waukegan

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Stewart to O'Hare Intl

John F Kennedy Intl to O'Hare Intl flights

Newark to O'Hare Intl flights

LaGuardia to O'Hare Intl flights

John F Kennedy Intl to Midway flights

Newark to Midway flights

LaGuardia to Midway flights

White Plains to O'Hare Intl flights

Rochester to O'Hare Intl flights

Buffalo to O'Hare Intl flights

Albany to O'Hare Intl flights

Syracuse to O'Hare Intl flights

Rochester to Midway flights

Syracuse to Midway flights

Buffalo to Midway flights

White Plains to Midway flights

Albany to Midway flights

Islip to O'Hare Intl flights

Ithaca to O'Hare Intl flights

Newark to Rockford flights

Binghamton to O'Hare Intl flights

Binghamton to Midway flights

Ithaca to Midway flights

Stewart to Rockford flights

Elmira to O'Hare Intl flights

Elmira to Midway flights

Plattsburgh to O'Hare Intl flights

Watertown to O'Hare Intl flights

Rutland to O'Hare Intl flights

Niagara Falls to O'Hare Intl flights

Saranac Lake to O'Hare Intl flights

Stewart to Midway flights

Other flights to O'Hare Intl

Myrtle Beach to O'Hare Intl flights

Atlanta to O'Hare Intl flights

Fort Myers to O'Hare Intl flights

Nashville to O'Hare Intl flights

John F Kennedy Intl to O'Hare Intl flights

New Haven to O'Hare Intl flights

Chicago O'Hare Intl Airport to Grand Rapids flights

Chicago O'Hare Intl Airport to Fort Myers flights

Chicago O'Hare Intl Airport to Nashville flights

Chicago O'Hare Intl Airport to Atlanta flights

Chicago O'Hare Intl Airport to St. Louis flights

Chicago O'Hare Intl Airport to Pittsburgh flights

Chicago O'Hare Intl Airport to Louisville flights

Chicago O'Hare Intl Airport to Orlando Airport flights

Chicago O'Hare Intl Airport to Las Vegas flights

Chicago O'Hare Intl Airport to Muskegon flights

Chicago O'Hare Intl Airport to Minneapolis flights

Chicago O'Hare Intl Airport to Nashville flights

Chicago O'Hare Intl Airport to San Diego flights

Chicago O'Hare Intl Airport to Fort Lauderdale flights

Chicago O'Hare Intl Airport to Miami flights

Chicago O'Hare Intl Airport to Baltimore flights

Chicago O'Hare Intl Airport to Cleveland flights

Chicago O'Hare Intl Airport to Owensboro flights

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.

$94+ Cheap flights from New Windsor (SWF) to O'Hare Intl (ORD)

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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to O'Hare Intl 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 O'Hare Intl

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to O'Hare Intl

Cheapest flights from Stewart to O'Hare IntlExplore the most affordable flight options available from Stewart to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

Explore the most affordable flight options available from Stewart to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Chicago O'Hare Intl Airport that are best for you.

Best time to book a flight from Stewart to O'Hare Intl

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

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from New Windsor to Chicago O'Hare Intl Airport?

Related info for your journey

Find useful and relevant information for your journey from Stewart to O'Hare Intl. 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 O'Hare Intl?

Can I find deals for flights from Stewart to O'Hare Intl that include hotel bookings?

How can I find direct flights from Stewart to O'Hare Intl?

Can I find deals for business class flights from Stewart to O'Hare Intl?

What is the cheapest month to book a flight from New Windsor to Chicago O'Hare Intl Airport?

Traveling to a place near Chicago O'Hare Intl Airport?

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 O'Hare Intl

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 O'Hare Intl
Explore the most affordable flight options available from Stewart to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.