C$372 Cheap Flights from Chicago (CHIA) to Stewart International (SWF)

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Flight deals from Chicago to Stewart International

Looking for a cheap last-minute deal or the best return flight from Chicago to Stewart International Airport? If you want to travel next month, return fares start from C$394. Find the lowest prices on one-way and return tickets right here.

New York.C$135 per passenger.Departing Wed., Aug. 5.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed., Aug. 5, arriving in Stewart International.Price includes taxes and charges.From C$135, select.

New York.C$153 per passenger.Departing Wed., Jul. 22.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed., Jul. 22, arriving in Stewart International.Price includes taxes and charges.From C$153, select.

New York.C$177 per passenger.Departing Sun., Sep. 6.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun., Sep. 6, arriving in Stewart International.Price includes taxes and charges.From C$177, select.

New York.C$182 per passenger.Departing Mon., Oct. 19.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon., Oct. 19, arriving in Stewart International.Price includes taxes and charges.From C$182, select.

New York.C$217 per passenger.Departing Sun., Nov. 1.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Sun., Nov. 1, arriving in Stewart International.Price includes taxes and charges.From C$217, select.

New York.C$234 per passenger.Departing Mon., Jun. 29.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Mon., Jun. 29, arriving in Stewart International.Price includes taxes and charges.From C$234, select.

New York.C$275 per passenger.Departing Fri., Jan. 29.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri., Jan. 29, arriving in Stewart International.Price includes taxes and charges.From C$275, select.

New York.C$285 per passenger.Departing Wed., Dec. 2.One-way flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Wed., Dec. 2, arriving in Stewart International.Price includes taxes and charges.From C$285, select.

New York.C$518 per passenger.Departing Fri., Mar. 5.One-way flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Fri., Mar. 5, arriving in Stewart International.Price includes taxes and charges.From C$518, select.

New York.C$1,605 per passenger.Departing Sun., Feb. 14.One-way flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Sun., Feb. 14, arriving in Stewart International.Price includes taxes and charges.From C$1,605, select.

Find the cheapest month to fly from Chicago to Stewart International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Stewart International flights are currently cheapest in August.

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Chicago to Stewart International: Alternative routes

Compare routes from Chicago to New York below. You may find an airport to fly into that's cheaper, faster, or easier than Stewart International.

Chicago to New York: Flight information

The things to know before you go.

Cheapest flight found	C$135
Cheapest month to fly	August

Finding cheap flights from Chicago to Stewart International: Frequently asked questions

How much are return flights from Chicago to Stewart International?

The best price we found for a return flight from Chicago to Stewart International is C$372. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Chicago to Stewart International?

Currently, there are no airlines that fly direct from Chicago to Stewart International. But we found flights with one stop from C$372.

How many flights are there a week from Chicago to Stewart International?

As of June 2026, there are no flights flying from Chicago to Stewart International.

When is the cheapest time to fly from Chicago to Stewart International?

The cheapest month to fly from Chicago to Stewart International is usually August.

Which upcoming date is cheapest to fly from Chicago to Stewart International Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Stewart International Airport on Monday, August 31, 2026.

Can I get a direct flight from Chicago to Stewart International Airport?

No airlines currently offer direct flights between Chicago and Stewart International Airport. Most routes have one or more stops.

How can I find the best flight deal to Stewart International?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Stewart International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to New York?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to New York is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Chicago to Stewart International with?

The cheapest airline that flies to Stewart International is Allegiant Air .

Flying from Chicago to Stewart International Airport (SWF): what you need to know

Begin your trip planning by checking out the ideal departure point for your flight from Chicago to Stewart International Airport (SWF). Explore the options for taking off from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.
New York is 1 hour ahead of Chicago. Stewart International Airport is located in New York, which operates on the UTC-4 timezone.
For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from Chicago to SWF.
With more travellers during busy months like August, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will allow for extra wait times. Remember things also get busy during major holidays like Christmas.

Airports in Chicago

O'Hare International Airport (ORD)

From the centre of Chicago, ORD is around 40 kilometres away. Use navigation apps or visit the official airport website to find the best way to arrive at the terminal.
Need a convenient hotel near O'Hare International Airport? If you've booked an early flight from Chicago to Stewart International Airport, these accommodation options will have you moments from your check-in counter:

Chicago Midway International Airport (MDW)

You can arrive at MDW from the centre of Chicago in approximately 21 minutes by car (depending on traffic conditions). The ride by public transport takes roughly 46 minutes to travel the 19 kilometres or so.
Start your vacation early with an extra night away from home. Before catching your flight from Chicago to SWF, take it easy in one of these hotels close to Chicago Midway International Airport:

About Stewart International Airport (SWF)

Consider staying in a hotel close to SWF if you're taking a late flight from Chicago to Stewart International Airport. Check in to one of these options and avoid the hassle of a long transfer:

Getting from Stewart International Airport (SWF) to central New York

Stewart International Airport is approximately 121 kilometres from the centre of New York. With your own car rental or if you take a cab, the drive is around 1 hour and 31 minutes.
If you're travelling on public transport, expect a journey time of around 1 hour and 57 minutes.

How to find the cheapest flights from Chicago to Stewart International Airport (SWF)

Pick up a one-way ticket from Chicago to Stewart International Airport from C$135 or travel return from just C$372. The prices shown are based on availability and could change when you book.
We recommend booking as soon as you can to lock in flight tickets from Chicago to SWF. You're more likely to snag a great deal and have a wider selection of flight times and dates.
If you're flexible with your travel plans, make the most of the 'Whole month' tool. It'll find the lowest price across the month when searching for your ticket from Chicago to Stewart International Airport.
Set up a Price Alert and track any changes on this route through email or push notifications. You'll be the first to know when prices drop. It's all about timing when scoring flight tickets from Chicago to SWF.
Tailor your flights with filters. Pick your preferred departure and arrival times, airlines and total journey duration. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago to Stewart International Airport.

The best time to fly from Chicago to Stewart International Airport (SWF)

It's time to pick your trip dates for your flight from Chicago to Stewart International Airport. July is the busiest month to travel to New York. If you prefer a more peaceful vibe, go in April.
Before locking in your flight from Chicago to SWF, think about the type of weather you enjoy. July is the warmest month in New York, with the temperature ranging from 18ºC to 30ºC.
Visit in January for cooler conditions. Average temperatures range between -6ºC and 8ºC. However, this city promises a good time whenever you book your cheap flights from Chicago to Stewart International Airport.

More about New York

Start your New York trip off on the right foot by choosing the perfect place to stay. As soon as you've booked your flight from Chicago to Stewart International Airport, browse our selection of hotels including:
All great adventures should include a little sightseeing. Statue of Liberty, Central Park and Empire State Building are must-visits when exploring New York.

Complete your New York trip with a car rental

Grab the keys to one of our car rentals in New York and see the sights at your own pace. Easily compare rates from trusted providers in one go after booking your hotel and cheap flights from Chicago to Stewart International Airport.