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New York Stewart International Airport to Chicago flight

Search for flights from New York Stewart International Airport to Chicago and check out affordable one-way and round-trip options.

      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Oct 10 | Normal Airline
        Search
        Search
      • SWF 11:48
        21h 57m
        1 stop
        MDW 08:45
        New York - Chicago | Thu, Oct 29 | Allegiant Air
        CAD 266 CAD 365
        27% off
        27% off
        CAD 365 CAD 266
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Oct 8 | Normal Airline
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Flight fares from New York Stewart International Airport to Chicago are based on average prices across airlines for the next three months, according to Trip.com’s latest data.

Which airlines are the most popular for New York Stewart International Airport to Chicago flights?

See which airlines fly from New York Stewart International Airport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.
United Airlines logo United Airlines
Delta Air Lines logo Delta Air Lines

What to know about flights from New York Stewart International Airport to Chicago?

Cheapest return ticket price CAD 260
Cheapest one-way flight price CAD 125
Off-season travel month August
Peak season for travel January

FAQs for New York Stewart International Airport to Chicago Flights

  • When is peak season for travel to Chicago?

    ؜The peak travel time for visiting Chicago is October. During this time, flights from New York Stewart International Airport to Chicago are the most expensive. Cheap tickets can still be booked on Trip.com.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • Based on Trip.com flight data for departures within the next 30 days, the average one-way fare from New York Stewart International Airport to Chicago is CAD 293, and the average round-trip fare is null. Prices may vary depending on the departure date, airline, and availability.

Find Cheap Flights with Trip.com

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

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Prices displayed on this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within the last 24 hours—even in real-time. The more popular the route, the more precise the data.

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