Toronto to Chicago (YYZ–MDW) — Airlines, Schedules & Connections

YYZ Airport Page →
432 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 52 1-stop flights Verified 1h ago
Also flown by charter / private operators.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
DTW Detroit 3h 26m ACAFAM → AFDLKE Detroit (DTW) to Chicago flights
CLE Cleveland 3h 34m ACEJAUA → WN Cleveland (CLE) to Chicago flights
CVG Cincinnati / Covington 3h 45m ACUA → WN Cincinnati / Covington (CVG) to Chicago flights
IND Indianapolis 3h 55m ACDLUA → EJAWN Indianapolis (IND) to Chicago flights
PIT Pittsburgh 4h ACUA → EJAWN Pittsburgh (PIT) to Chicago flights
DCA Washington 4h 25m AAACPD → WN Washington (DCA) to Chicago flights
PHL Philadelphia 4h 25m AAACJRE → EJAKOWWN Philadelphia (PHL) to Chicago flights
PVD Providence/Warwick 4h 30m AC → EJAWN Providence/Warwick (PVD) to Chicago flights
STL St Louis 4h 33m ACUA → WN St Louis (STL) to Chicago flights
MSP Minneapolis 4h 38m ACAMASP → AFDLEJA Minneapolis (MSP) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Toronto to Chicago
Connecting service available through multiple hubs.
1 Airlines 432 mi 1h 11m nonstop -1h behind

YYZ–MDW had nonstop service, last on the schedule in June 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 432 miles in 1h 11m.

Also explore YYZ Routes MDW Routes YYZ Live Flights MDW Live Flights YYZ Delays MDW Delays
All flights from Chicago (MDW) Chicago to Toronto flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop YYZ–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
HTT HTT 0 – – 67% – –
Alliance coverage
Unaffiliated: HTT (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for YYZ to MDW.
1-STOP
One-Stop Connections
52
Hubs
~3h
Fastest
~21h
Longest
DTW ~3h 26m CLE ~3h 34m CVG ~3h 45m IND ~3h 55m PIT ~4h 0m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
3,159
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
YYZ → MDW
67%
Moderate delays possible. Allow buffer time.
Departing
67%
Arriving
59%
Return
MDW → YYZ
53%
Frequent delays expected. Consider flexible booking.
Departing
53%
Arriving
87%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. YYZ delays → MDW delays →
Alternatives

Other ways to reach Chicago from Toronto

Nearby airports with service to Chicago Midway International Airport.
Metric YYZ→MDW YTZ→MDW YKF→MDW
Distance from YYZ – 12 mi 40 mi
Nonstop airlines – 4 2
Weekly flights – 26 1
Flight time 1h 11m 1h 50m 1h 6m
Departure OTP 67% – –
Toronto (YTZ) to Chicago flights · Breslau (YKF) to Chicago flights · Buffalo (BUF) to Chicago flights
Airports within 200 miles of YYZ with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind Toronto.
YYZ: EDT · MDW: CDT

When it's 6:00 PM in Toronto, it's 5:00 PM in Chicago.
Distance & Flight Time
432 mi / 696 km
Nonstop flight time is approximately 1h 11m gate to gate.
Visa & Entry

Canadian citizens do not need a visa or ESTA to enter the United States for tourism or business stays up to 6 months. A valid Canadian passport is required for air travel. Land and sea crossings also accept a NEXUS card, enhanced driver's license, or FAST card. At the border, officers determine the length of stay and may ask for proof of ties to Canada and a return plan.

Verify entry requirements with official sources before travel.
Getting to YYZ

The UP Express train runs from Union Station (downtown Toronto) to Terminal 1 in 25 minutes (CAD $12.35). Trains depart every 15 minutes during peak hours, every 30 minutes off-peak and overnight. Highway 427 and the 401 are heavily congested during rush hours.

Taxis and ride-hail from downtown cost CAD $50–70 and take 25–60 minutes depending on traffic. MiWay and Brampton Transit buses serve the airport from the western suburbs. Long-term parking is available in the Viscount Road lots with free shuttle service.

Facts

YYZ–MDW Quick Facts

Key statistics for the Toronto to Chicago route.
Route details
Distance432 mi / 696 km
Flight time1h 11m
Time difference-1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: YYZ
Full nameToronto Pearson International Airport
IATA / ICAOYYZ / CYYZ
TimezoneAmerica/Toronto
Passengers/yr46.8M
Elevation569 ft / 173 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about YYZ to MDW flights.
Nonstop flights from Toronto Pearson International Airport to Chicago Midway International Airport take about 1h 11m gate to gate. The route covers 432 miles.
1 airline operated the nonstop from YYZ to MDW. The last scheduled nonstop was in June 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in June 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 1h 11m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Detroit Metropolitan Wayne County, Cleveland Hopkins and Cincinnati Northern Kentucky.
Chicago is 1 hour behind Toronto.
Yes, return flights from MDW to YYZ are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include YTZ, YKF and BUF. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from YYZ to MDW

Toronto Pearson International Airport (YYZ) and Chicago Midway International Airport (MDW) had nonstop service, last on the schedule in June 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

YYZ to MDW Flight Duration and Schedule

Nonstop flight time from YYZ to MDW is about 1 hours 11 minutes gate to gate. The route covers a distance of 432 miles (696 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Detroit Metropolitan Wayne County, Cleveland Hopkins and Cincinnati Northern Kentucky. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Toronto (YTZ), Breslau (YKF) and Buffalo (BUF).