Trip.com
>
Cheap Flights
>
United States
>
Chicago
>
New York to Chicago flight
>
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

Displayed flight fares from New York Stewart International Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months according to the latest Trip.com 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.

Find Cheap Flights with Trip.com

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

Book with no extra fees

Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, 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 have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
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 according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please visit the customer support pages.