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New York Stewart International Airport to Chicago Midway International Airport flight

Search for flights from New York 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, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search

Flight fares from New York Stewart International Airport to Chicago Midway International Airport are based on the average fares across airlines for the next three months, based on Trip.com’s latest data.

About New York Stewart International Airport and Chicago Midway International Airport

Learn about New York Stewart International Airport (SWF) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 1,133.95km

FAQs for New York Stewart International Airport to Chicago Midway International Airport Flights

  • What is the transportation method from the main airport to downtown in Chicago?

    • 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.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • Enter New York Stewart International Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

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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 in this page are all-inclusive prices (incl. taxes, fuel surcharge, regulatory fees, etc) with all fees confirmed before payment. Fees for baggage, 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 last 24 hours—even in real-time. The more popular the route, the more precise the data.

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