Canada to United States · 442 miles (711 km)

Toronto (YTZ) to Chicago (MDW) flights

One airline flies nonstop from Toronto (YTZ) to Chicago (MDW): Porter Airlines. The two airports are 442 miles (711 km) apart. There are also 3 ways to fly it with one stop, through Nashville, New York and Boston.

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Airlines flying nonstop from YTZ to MDW

  • Porter Airlines logo
    Porter AirlinesNot in an alliance · bookable with 1 programWho books it

Book YTZ to MDW with points

Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.

YTZ to MDW with one stop

3 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.

  • Via Nashville (BNA)Porter Airlines, then Southwest Airlines
    Porter Airlines logo
    Southwest Airlines logo
  • Via New York (LGA)Air Canada, then Southwest Airlines
    Air Canada logo
    Southwest Airlines logo
  • Via Boston (BOS)Porter Airlines and Air Canada, then Southwest Airlines
    Porter Airlines logo
    Air Canada logo
    Southwest Airlines logo

YTZ to MDW: common questions

Which airlines fly nonstop from YTZ to MDW?

Porter Airlines flies nonstop from Toronto (YTZ) to Chicago (MDW).

How far is Toronto from Chicago by plane?

Toronto (YTZ) and Chicago (MDW) are 442 miles (711 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.

Which points programs can book YTZ to MDW award flights?

1 program can book at least one of the nonstop airlines: Alaska Atmos Rewards. Which flights each can book depends on its partners, so check the airline before you transfer points.

How many miles does YTZ to MDW cost?

It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for YTZ to MDW with taxes and fees.

Where can I connect between Toronto and Chicago?

The most direct connections are through Nashville (BNA), New York (LGA) and Boston (BOS).

More routes

MDW to YTZEvery nonstop from YTZEvery nonstop from MDW

Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.