Cheap Flights from Stewart International (SWF) to Chicago (CHIA)

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Flight deals from Stewart International to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Stewart International to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Stewart International to Chicago

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

Alternative Stewart International to Chicago routes

Looking for the cheapest, fastest or easiest route from Stewart International to Chicago? You could fly into the following airports instead.

New York to Chicago: Flight information

The things to know before you go.
Cheapest flight found$99
Cheapest month to flyJune

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Stewart International to Chicago is $210. 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. But we found flights with one or more stops from $210.
There are no flights flying from Stewart International to Chicago, as of May 2025.
The cheapest month to fly from Stewart International to Chicago is usually May 2025.
If you're flying from Stewart International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $210.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Stewart International Airport to Chicago on Friday, August 8, 2025.
No airlines currently offer direct flights between Stewart International Airport and Chicago. 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 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.
In May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
Currently, Allegiant Air offers the cheapest flight tickets to Chicago.

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

  • The timezone in Chicago is UTC-5. The city is one hour behind New York, where Stewart International Airport is located.

  • Leave plenty of time to get on your SWF to Chicago flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • Heading off during a peak period like school or public holidays? Expect longer lines at check-in and security. To play it safe, arrive up to four hours before international flights and two hours ahead of domestic departures.

  • Traveling from central New York to SWF takes around 1 hour 55 minutes by public transport. If you ride-share, drive or grab a cab, you'll cover the 0.1 miles in 1 hour 30 minutes or so, depending on traffic.

  • Want a relaxed start to your travels? Stay near SWF. Whether you're catching an early flight from Stewart International Airport to Chicago or want to avoid feeling rushed, these hotels have you covered:

  • 83.75% of flights leaving Stewart International Airport reach their destination on schedule. With its strong performance rating, delays are unlikely when jetting out of SWF.

  • You'll find SWF at 1180 1st St.

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

  • $99 is the cheapest price we've found for a one-way Stewart International Airport to Chicago flight. A return plane ticket right now is $210. Depending on how early you book and the availability, these fares may change.

  • Don't wait until the last moment. You're more likely to land cheap flights from SWF to Chicago if you book early. Airlines often offer some amazing early bird discounts.

  • Finding cheap tickets from Stewart International Airport to Chicago is easier if you're flexible with your dates. Try using the 'Whole month' search function to get the lowest prices across every month and score a sweet deal.

  • You don't need to check in daily to see if fares have dropped when you set up a Price Alert. We'll let you know when there's an updated deal for cheap flights from SWF to Chicago.

  • Save money on your flight from Stewart International Airport to Chicago with the help of our filters. Select your preferred departure time, duration and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 25 miles. It takes about 35 minutes to reach the center driving.

  • Getting to the center on public transport takes about 55 minutes.

  • Book a hotel close to ORD if you're coming in on a late flight from Stewart International Airport to Chicago. Check in to one of these accommodation options and make your arrival easier:

  • Begin your adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and experience the lesser-explored corners of Chicago and beyond.

  • Lock in the best rate by booking your vehicle from O'Hare International Airport about four weeks before your flight from SWF to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Stewart International Airport to Chicago has arrived, you can get to the city center in around 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • If you choose to travel on public transport, the journey will take you 45 minutes or so.

  • Following your SWF to Chicago flight, tuck yourself in at a hotel near MDW. These are some great accommodation options that'll help you switch to relaxation mode:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These providers are located in or around the terminal and will have you on your way in a heartbeat.

  • Get exactly what you want. Reserving your ride from MDW four weeks in advance often means lower prices and a greater selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make tracks for the city center after your flight from Stewart International Airport to Chicago has arrived. Central Chicago is about 85 miles from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.

  • The journey will take you about 4 hours 15 minutes by public transport.

  • If you don't want to make the trip to the center, head for a hotel near RFD. Make yourself comfy at one of these options after your SWF to Chicago flight:

  • Stay in control of the next part of your trip with a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • If you're hoping for a particular type of vehicle, booking early gives you a better shot at getting your first choice. Book your ride from RFD a couple of weeks ahead of your flight from Stewart International Airport to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago in high season if you like a busy atmosphere, but remember that prices are generally higher. Alternatively, book flights from Stewart International Airport to Chicago during low season when prices are cheaper and it's quieter.

  • The warmest month in Chicago is July, with temperatures ranging between 59ºF and 84ºF. Book your Stewart International Airport to Chicago plane ticket then if that's your idea of comfortable weather.

  • Search for cheap tickets from SWF to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between 10ºF and 37ºF on average.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Check out these hotels once you've booked your flight from Stewart International Airport to Chicago:

  • There are so many things to explore in this city it can be tricky to know where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are leading attractions which should be on any well-planned Chicago itinerary.

Explore more of United States

  • Chicago is always a good idea, but there are so many other parts of United States you should also see. About 280 miles south-east of Chicago, a trip to Columbus will keep your itinerary busy. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another sought-after destination in United States and is around 160 miles 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 45 days.