What this Chicago & Toronto page shows
This page compares the full metro areas of Chicago (ORD, MDW) and Toronto (YYZ, YTZ) and lists every destination both cities can reach on a nonstop flight: 108 in all, across 47 countries and 10 regions. For each one you can see the flight time and distance from CHI and from YYZ, so the trade-off between the two legs is clear at a glance.
Use the map to see how far the options spread, then check the meet-in-the-middle pick (Detroit has the smallest gap in flight distance here) before opening the full table to sort all 108 shared routes. To filter by month and check live fares, open the Midway app with Chicago and Toronto already loaded.
Where you can both fly
Every marker is a destination with nonstop service from both Chicago and Toronto. The spread runs from Indianapolis close by to Manila at the far edge, so you can gauge whether a short hop or a long-haul meet-up makes more sense.
All shared destinations
Each row is a destination both cities reach nonstop. The two right-hand columns give the flight time and distance from CHI and from YYZ. When those two legs are close, the trip splits evenly between Chicago and Toronto. Open the full table in Midway to sort by either leg or filter by month.
Where in the world
Shared destinations grouped by region — 108 in total across 10 regions.
Year-round or seasonal
67% of these routes fly year-round, with 36 running only in certain seasons. If your meet-up date is flexible you have the full set to choose from; if it is fixed, lean toward the year-round destinations so you are not counting on a route that may not be flying that month.
Related Routes
Frequently asked questions
How many nonstop destinations do Chicago and Toronto share?
Travelers from Chicago and Toronto have 108 common nonstop options, covering 10 regions and 47 countries.
What is the closest place both Chicago and Toronto can fly to nonstop?
Indianapolis is the closest shared nonstop destination for Chicago and Toronto.
Where should travelers from Chicago and Toronto meet halfway?
Detroit is the most balanced shared destination, with the smallest difference in flight distance from the two cities.
What is the farthest shared nonstop destination from Chicago and Toronto?
Manila is the farthest destination both Chicago and Toronto can reach nonstop.
Open Chicago and Toronto in Midway
Filter by month, distance, flight time, country and region, see prices from each city, and send the link to your group.
Last updated: October 5, 2026