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 — 109 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 your options spread, then check the meet-in-the-middle pick — Detroit is the most balanced destination here before opening the full table to sort all 109 shared routes. When you are ready 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 — 109 in total across 10 regions.
Year-round or seasonal
66% of these routes fly year-round, with 37 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 109 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 — roughly equidistant by flight distance for both cities.
What is the farthest shared nonstop destination from Chicago and Toronto?
Manila is the farthest destination both Chicago and Toronto can reach nonstop.
Explore Chicago + Toronto on the interactive map
Filter by month, distance, flight time, country and region. Get prices — and share the results with your group.
Last updated: August 15, 2026