Toronto (YYZ) to Chicago (ORD) is about 440 miles and typically takes 1 h 25 min by air. It is an international route, so check passport and entry rules. Airlines with hubs at both ends are the likeliest to offer nonstops; otherwise expect a connection. Call (800) 490-3234 for live fares.
YYZ to ORD at a glance
| Route | Toronto (YYZ) to Chicago (ORD) |
|---|---|
| Distance | about 440 miles / 700 km |
| Typical flight time | 1 h 25 min (estimate) |
| Time difference | 1 hours behind |
| Route type | International |
| Airlines with hubs here | American Airlines, United Airlines, and Air Canada |
About the Toronto to Chicago route
Toronto to Chicago is an international trip of about 440 miles, so planning begins with paperwork as much as with the ticket. Your passport, any entry authorization for the United States and your connection plan matter as much as the fare.
Flight time and distance
A typical flight takes about 1 h 25 min gate to gate, with a realistic range of 1 h 05 min to 1 h 50 min depending on wind, routing and aircraft. That is an estimate based on the distance of roughly 440 miles (700 km), not a published schedule.
Chicago is 1 hour behind Toronto on standard time, so the arrival time on your ticket will look different from the flight duration.
Among the 200 routes in our guides, YYZ to ORD is longer than about 8% of them.
For comparison, Toronto to New York (YYZ to JFK) is about 370 miles, so Chicago is a bit farther out from YYZ.
The airports
Toronto Pearson International Airport (YYZ)
Pearson is Canada's busiest airport and the main hub for Air Canada. Full YYZ guide.
O'Hare International Airport (ORD)
O'Hare is a dual hub for United and American and one of the busiest airports in the world by flight volume, with nonstops to most major U.S. cities and a long list of international destinations. Full ORD guide.
Other airports are worth a look: around Chicago, Midway (MDW). Comparing them can change the price or the travel time to your final destination.
Airlines on this route
No single carrier we cover has hubs at both YYZ and ORD. American Airlines (at ORD), United Airlines (at ORD), and Air Canada (at YYZ) each operate a large network at one end, so many itineraries on this route connect rather than fly nonstop.
Airlines add and drop frequencies throughout the year. Our agents can check what is actually scheduled on your dates.
Common connection points
A one-stop trip would most naturally connect through a hub such as United Airlines via Washington, D.C. (IAD), which adds about 500 miles (114% beyond the direct distance) or American Airlines via Washington, D.C. (DCA), which adds about 530 miles (123% beyond the direct distance). Choose the connection with the best weather odds for your travel month and leave a comfortable layover; our layover guide explains how much time is realistic.
Best time to fly
Timing matters here. At ORD, winter storms and summer thunderstorms are the main triggers for delays; connecting through O'Hare in January deserves extra buffer. At YYZ, winter weather can slow operations; summer is busy with visiting travelers.
Ground transport
Getting to and from YYZ
The UP Express train reaches Union Station in about 25 minutes.
Getting to and from ORD
The CTA Blue Line runs 24 hours into downtown Chicago in about 45 minutes.
Booking tips
Check passport validity and entry rules for the United States before you book, and make sure the name on your ticket matches your passport exactly. Our international checklist lists what to confirm.
Frequently asked questions
How long is the flight from Toronto to Chicago?
A typical YYZ to ORD flight takes about 1 h 25 min, with a likely range of 1 h 05 min to 1 h 50 min. Actual time depends on wind, routing, aircraft and whether you connect.
How far is Chicago from Toronto by air?
The great-circle distance between YYZ and ORD is about 440 miles (700 km).
Which airlines fly from Toronto to Chicago?
American Airlines, United Airlines, and Air Canada have a major presence at YYZ or ORD, and service varies by season. Ask us to check current nonstop and connecting options.
What is the time difference between Toronto and Chicago?
Chicago is 1 hour behind Toronto on standard time. Daylight saving time can change the gap for part of the year.
Do I need a passport to fly from Toronto to Chicago?
Yes, international flights require a valid passport, and the United States may have additional entry or visa rules. Check the official government site before booking.
When is the best time to book YYZ to ORD?
Domestic fares are often competitive one to three months ahead, while international trips benefit from more lead time. Compare several dates, since fares are priced flight by flight.
Explore related routes
More flights involving Toronto (YYZ)
More flights involving Chicago (ORD)
- Anchorage to ChicagoANC to ORD
- Austin to ChicagoAUS to ORD
- Chicago to AtlantaORD to ATL
- Chicago to BostonORD to BOS
- Chicago to ClevelandORD to CLE
- Chicago to DallasORD to DFW
Last reviewed October 22, 2026. FlighTicketHub provides general information; confirm details with the airline before you travel.