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

YYZ Airport Page →
432 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 137 1-stop flights Verified 1w ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Toronto to Chicago
1 carrier, 1 flights/week nonstop.
1 Airlines 1 Flights/wk 432 mi 2h 3m nonstop -1h behind 137 1-stop hubs

YYZ–MDW is served by 1 airline with nonstop service. HTT leads the route. The flight covers 432 miles in approximately 2h 3m. Beyond nonstop, 137 hubs offer 1-stop connections.

Also explore YYZ Routes MDW Routes YYZ Live Flights MDW Live Flights YYZ Delays MDW Delays
Carriers on this route

Airline Landscape

All carriers operating nonstop YYZ–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
HTT HTT 0 – – 82% – –
Alliance coverage
Unaffiliated: HTT (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for YYZ to MDW.
1-STOP
One-Stop Connections
137
Hubs
~3h
Fastest
~31h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
3,432
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.
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 1 3 1
Weekly flights 1 20 1
Flight time 2h 3m 1h 50m 1h 8m
Departure OTP 82% – –
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 2h 3m.
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 time2h 3m
Time difference-1 hour
Airlines (nonstop)1
Weekly flights1 out / 1 return
1-stop connections137 hubs
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 approximately 2h 3m. The route covers 432 miles.
1 airline operates nonstop service: HTT.
There are approximately 1 nonstop flights per week from YYZ to MDW. The return direction has about 1 weekly flights.
Yes, 1-stop connections are available through YIP, PTK, GRB, MKC, CAK, DAY, BUF, STP, SDF, YKF, MKE, DPA, ABE, GRR, BTV, TEB, GSO, MMU, SWF, HPN, BED, FRG, ALB, RIC, RST, BWI, TYS, DSM, IAD, PDK, YOW, OXC, FTY, NEW, BDL, GSP, MCI, MHT, ACY, MEM, OMA, ORF, PVD, YUL, FAR, YHU, JAX, MCN, ORL, SAV, SGR, DAL, ADS, VRB, BJC, HOU, PIE, SUA, APA, PBI, MHH, BCT, FXE, APF, SAT, EGE, OPF, BZN, SCF, TMB, IAH, FPO, NAS, GGT, BOI, TUS, MID, YEG, VNY, GCM, PLS, CLD, OKC, YVR, PSP, ORD, EIS, GDL, SMF, OAK, RNO, PIT, SJD, LGB, SJU, SXM, SKB, SJC, TPA, SEA, CUN, DTW, SRQ, CVG, AUS, ATL, CLE, LBG, FLL, CLT, DFW, MSP, STL, EWR, DCA, LGA, PHX, SLC, RDU, IND, SAN, PHL, MSY, BOS, BNA, RSW, CMH, MCO, SFO, LAS, DEN, LAX, MIA, MBJ, CHS, BTL and PUJ. These options provide additional schedule flexibility.
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) are connected by nonstop service from HTT. With 1 weekly departures, this is a regularly served route.

YYZ to MDW Flight Duration and Schedule

Nonstop flight time from YYZ to MDW ranges from 2 hours 3 minutes. The route covers a distance of 432 miles (696 km). There are approximately 1 weekly flights outbound and 1 return, totaling 2 flights per week in both directions.

Connecting Options and Alternatives

137 one-stop connections are available, with the fastest taking approximately 3 hours via YIP. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Toronto (YTZ), Breslau (YKF) and Buffalo (BUF).