Cheap Flights from Stewart International to Chicago O'Hare International

Compare Stewart International to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

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Flight deals from Stewart International to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Stewart International Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from R 5,396. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Stewart International to Chicago O'Hare International

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

Stewart International to Chicago O'Hare International: Alternative routes

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

New York to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,931
Cheapest month to flyNovember

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

The best price we found for a return flight from Stewart International to Chicago O'Hare International is R 4,234. 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.
Currently, there are no airlines that fly direct from Stewart International to Chicago O'Hare International. But we found flights with one or more stops from R 4,234.
As of July 2026, there are no flights flying from Stewart International to Chicago O'Hare International.
The cheapest month to fly from Stewart International to Chicago O'Hare International is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Stewart International Airport to Chicago O'Hare International Airport on Thursday, 1 October 2026.
No airlines currently offer direct flights between Stewart International Airport and Chicago O'Hare International Airport. Most routes have one or more stops.
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 Chicago O'Hare 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.

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

Currently, Allegiant Air offers the cheapest flight tickets to Chicago O'Hare International.

Travelling from Stewart International Airport (SWF) to O'Hare International Airport (ORD): what you need to know

  • The timezone in Chicago is UTC-5, which is one hour behind New York.

  • To ensure you catch your SWF to ORD flight, leave plenty of time for things like check-in and baggage drop. Turning up two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • You'll likely experience longer lines during popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures is a good idea.

  • Consider adding a stopover when booking your ticket from Stewart International Airport to O'Hare International Airport. Just uncheck 'Direct flights only' to break up your trip, or perhaps see a new city along the way. Check out these options between SWF and ORD:

    • Myrtle Beach International Airport

    • Charleston International Airport

    • Orlando International Airport

How to find the cheapest flights from Stewart International Airport (SWF) to O'Hare International Airport (ORD)

  • R 1,931 is the lowest price for a one-way Stewart International Airport to O'Hare International Airport flight. Return flights start from R 4,234. These prices may change based on availability and demand.

  • It's a good idea to book in advance if you're hoping to get cheap tickets from SWF to ORD. That's because airlines adjust prices based on demand, which tends to rise closer to departure.

  • Finding cheap flights from Stewart International Airport to O'Hare International Airport is easier if you're flexible with your dates. Use the 'Whole month' search tool to see the lowest prices throughout the month and bag a great deal.

  • There's no need to check every day to find out if fares have gone down when you set up a Price Alert. We'll notify you as soon as there's a change in price on cheap flights from SWF to ORD.

  • Secure the ideal flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Stewart International Airport to O'Hare International Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about Stewart International Airport (SWF)

  • You'll find SWF at 1180 1st St.

  • 83.75% of flights leaving Stewart International Airport reach their destination according to schedule. With its impressive on-time stats, disruptions are unlikely when jetting out of SWF.

  • To get to Stewart International Airport from central New York, it'll take about 1 hour 30 minutes if you're travelling by car. This depends on traffic, however. It's approximately 121 kilometres from the airport to the city centre.

  • Expect a journey time of about 1 hour 55 minutes on public transport.

  • Booked an early flight from Stewart International Airport to O'Hare International Airport? Avoid rushing to the terminal (and catch some extra z's) by choosing one of these stays close to SWF:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • The address for ORD is 10000 West O'Hare.

  • O'Hare International Airport to the centre of Chicago has a drive time of around 35 minutes. It's approximately 40 kilometres away.

  • When travelling on public transport, expect a journey time of roughly 55 minutes.

When to fly to O'Hare International Airport (ORD)

  • The quietest month for a flight from Stewart International Airport to O'Hare International Airport is January, while August is the busiest. Pick the best time to go to Chicago based on whether you prefer a more fast-paced or easygoing experience.

  • Before locking in your flight from Stewart International Airport to O'Hare International Airport, think about the kind of weather you like. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you like cooler conditions, look for a cheap ticket from SWF to ORD in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • You've done Chicago, now it's time to discover more of United States. Journey about 451 kilometres south-east to Columbus to tick off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a packed itinerary ahead.

  • Indianapolis is another must-experience destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.