Cheap Flights from New York (SWF) to Chicago (CHIA)

Compare Stewart International to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Stewart International to Chicago

Looking for a cheap last-minute deal or the best return flight from Stewart International Airport to Chicago? If you want to travel next month, return fares start from $1,462. Find the lowest prices on one-way and return 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 October.

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$382
Cheapest month to flyOctober

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

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Stewart International to Chicago is $382. 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 $382.
As of July 2026, there are no flights flying from Stewart International to Chicago.
The cheapest month to fly from Stewart International to Chicago is usually October.
If you're flying from Stewart International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from $382.
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, 2 October 2026.
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 July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Allegiant Air offers the cheapest flight tickets to Chicago.

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

  • New York Stewart International Airport is located in New York. Following the UTC-6 timezone, Chicago is one hour behind New York.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your SWF to Chicago flight.

  • You can expect longer queues during popular months such as July. Arriving up to four hours in advance for international flights and two hours for a domestic departure will help ensure a smooth travel experience.

  • Located around 0.16 kilometres from central New York, SWF can be reached in about 1 hour 20 minutes by car. The journey on public transport takes roughly 1 hour 50 minutes.

  • Searching for a hotel near SWF? If you've booked an early flight from New York Stewart International Airport to Chicago, these accommodation options will put you moments from your departure lounge:

  • Of the flights that depart from New York Stewart International Airport, 76% land on time at their destination.

  • The address for SWF is 1180 1st St.

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

  • $173 is currently the best price for a one-way New York Stewart International Airport to Chicago flight. A return plane ticket starts from $382. These prices may change based on availability.

  • Booking ahead of time is often the key to securing a cheap flight from SWF to Chicago. Prices tend to rise as demand increases, so the closer your departure date, the more you'll likely spend.

  • Scoring cheap tickets from New York Stewart International Airport to Chicago is easier if you can be flexible with your dates. Try using the 'Whole month' search function to access the best prices across every month and bag an epic deal.

  • There's no need to check in daily to find out if fares have dropped when you create a Price Alert. We'll notify you the moment there's an updated deal for cheap flights from SWF to Chicago.

  • Save on your flight from New York Stewart International Airport to Chicago with the help of our filters. Choose your ideal times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It'll take you about 30 minutes to reach the centre driving.

  • If you're using public transport, expect a journey time of about 45 minutes.

  • Consider booking a hotel near ORD if you have a late flight from New York Stewart International Airport to Chicago. Pick one of these accommodation options and skip the long transfer:

  • Reserving your ride from Chicago O'Hare International Airport around four weeks ahead of your flight from SWF to Chicago can help you get the best possible rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). After your flight from New York Stewart International Airport to Chicago has hit the runway and you've navigated your way to arrivals, the drive should be around 25 minutes.

  • If you travel by public transport, you'll get to the city centre in 30 minutes or so.

  • Following your SWF to Chicago flight, kick back at a hotel near MDW. These are some comfortable options that'll help you sink into relaxation mode:

  • Snap up a deal by securing your ride from MDW four weeks ahead of time. You can also expect to have a greater selection of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 145 kilometres from central Chicago. It'll take you about 1 hour 40 minutes to reach the city centre by ride-share or taxi once you've hopped off your flight from New York Stewart International Airport to Chicago.

  • Public transport will take you there in about 2 hours.

  • If you don't want to make the trip into the centre, find a hotel near RFD. Check in to one of these stays after your SWF to Chicago flight:

  • If you'd like a specific make or model, booking early increases your chances of finding what you want. Secure your ride from RFD at least a couple of weeks ahead of your flight from New York Stewart International Airport to Chicago.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • It's time to figure out your dates for your flight from New York Stewart International Airport to Chicago. July is the busiest month to visit Chicago. If you like a quieter atmosphere, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your New York Stewart International Airport to Chicago plane ticket then if you enjoy this type of weather.

  • Search for cheap tickets from SWF to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the southeast, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If there's time to check out another corner of the United States, consider Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are highlights.

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