Toronto (YTZ) to Chicago (MDW) flights
An economy award from Toronto (YTZ) to Chicago (MDW) starts at 4,500 miles one way with Alaska Atmos Rewards on Porter Airlines, plus taxes and fees from $68.59. 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.
How many miles YTZ to MDW costs
Economy, one way, on the nonstop flights, from the Award Flight Pricer's award charts. Ranges run off-peak to peak; "from" is the floor of a dynamic price.
| Program | Economy | Taxes and fees |
|---|---|---|
| Alaska Atmos RewardsOn Porter Airlines | 4,500 | $68.59–88.59 |
Business and first class prices are in the Award Flight Pricer. Chart prices need award space on your date, so search it before you transfer points.
Compare every program in the Award Flight PricerAirlines flying nonstop from YTZ to MDW
- 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.
- Alaska Atmos RewardsBooks Porter Airlines
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
- Via New York (LGA)Air Canada, then Southwest Airlines
- Via Boston (BOS)Porter Airlines and Air Canada, then Southwest Airlines
YTZ to MDW: common questions
How many miles does YTZ to MDW cost?
In economy it starts at 4,500 miles one way with Alaska Atmos Rewards on Porter Airlines, plus taxes and fees from $68.59. These are award chart prices from the Award Flight Pricer. Programs that price dynamically can cost more on busy dates, so check yours before you transfer points. Business and first class prices are in the pricer too.
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.
Where can I connect between Toronto and Chicago?
The most direct connections are through Nashville (BNA), New York (LGA) and Boston (BOS).
More routes
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.