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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 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        NYC 4:00 PM
        Chicago - New York | Sat, Sep 12 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        New York - Chicago | Thu, Sep 10 | Normal Airline
        Search
        Search
      • NYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        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 average airline prices for the next 3 months, according to 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 1,133.95 km

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 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • 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 the lowest estimated prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before payment. Charges for checked baggage, onboard meals, Wi-Fi, and other optional services may also appear in the flight cards where applicable.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and for many routes the data may refresh in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

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Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.