International route
Cheap flights from Toronto to Chicago
Toronto Pearson International Airport (YYZ) to O'Hare International Airport (ORD). 436 miles, 1h 25m nonstop.
YYZ to ORD at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 436 milesgreat-circle
- Typical flight time
- 1h 25mnonstop, gate to gate
- Nonstop airlines
- AAUAWNAS10 airlinesAmerican, United, Southwest
- Nonstop flights per day
- 17all airlines combined
- Cheapest month
- October 2026over the next six months
- Best day to fly
- Tuesday16% less than Sunday
- Time difference
- 1h behindChicago vs Toronto
Toronto to Chicago
Round trips from $89
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Oct 13.
Cheapest month: October 2026
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppToronto to Chicago fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Toronto to Chicago
10 airlines fly nonstop with 17 departures a day combined, plus 2 more with one stop.
- AAAmerican AirlinesoneworldNonstop · 3 flights a day · first checked bag from $40
- UAUnited AirlinesStar AllianceNonstop · 3 flights a day · first checked bag from $40
- WSWestJetNonstop · 3 flights a day · first checked bag from $35
- ACAir CanadaStar AllianceNonstop · 2 flights a day · first checked bag from $35
- ASAlaska AirlinesoneworldNonstop · 1 flight a day · first checked bag from $35
- G4Allegiant AirLow-costNonstop · 1 flight a day · first checked bag from $50
- MXBreeze AirwaysLow-costNonstop · 1 flight a day · first checked bag from $45
- F9Frontier AirlinesLow-costNonstop · 1 flight a day · first checked bag from $55
- WNSouthwest AirlinesLow-costNonstop · 1 flight a day · first checked bag from $35
- SYSun Country AirlinesLow-costNonstop · 1 flight a day · first checked bag from $45
- DLDelta Air LinesSkyTeamConnecting via DTW · first checked bag from $35
- NKSpirit AirlinesLow-costConnecting via DTW · first checked bag from $55
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- Detroit (DTW)DLNK2 airlines
Which airport should I use?
Toronto has 2 airports and Chicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other departure airports near Toronto
Other arrival airports near Chicago
Tips for this route
- American, United, Southwest and Alaska all fly YYZ to ORD nonstop, so compare the total with bags before picking the lowest base fare: the difference between a basic and a standard economy ticket is often less than one checked bag each way.
- Departing on a Tuesday averages 16% less than a Sunday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays.
- At 436 miles this is a short hop of 1h 25m, so an early-morning departure, which is usually the cheapest and most punctual of the day, costs you little sleep.
Destination guide
Chicago: Big-shoulders architecture and a lakefront for everyone
Chicago is America's most connected inland hub — O'Hare and Midway between them have nonstops from nearly every US city — so fares are consistently reasonable. The lakefront, the architecture and the food make it a strong long weekend.
Best time to visit: June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Flying the other way? Chicago to TorontoFares, airlines and tips for ORD to YYZ.Ready to compare live fares?
See every airline on YYZ–ORD side by side with bags and seat rules spelled out.
Search Toronto to ChicagoToronto to Chicago: common questions
How long is the flight from Toronto to Chicago?
A nonstop flight from Toronto (YYZ) to Chicago (ORD) takes about 1h 25m gate to gate, covering 436 miles. Connecting itineraries add the layover, typically 2 to 5 hours more in total.
Which airlines fly nonstop from YYZ to ORD?
American Airlines, United Airlines, Southwest Airlines, Alaska Airlines, Frontier Airlines, Allegiant Air, Sun Country Airlines, Breeze Airways, Air Canada and WestJet operate nonstop flights from Toronto (YYZ) to Chicago (ORD), with 17 nonstop departures a day between them. One-stop options connect through DTW.
What is the cheapest month to fly from Toronto to Chicago?
Over the next six months, October 2026 has the lowest round-trip fares from Toronto (YYZ) to Chicago (ORD), starting at $89 per traveler including taxes and fees. Within any month, Tuesday departures average the lowest prices.
How far in advance should I book Toronto to Chicago flights?
Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Toronto and Chicago?
Chicago is 1 hour behind Toronto. YYZ is on America/Toronto time and ORD on America/Chicago time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
Other popular city pairs from the same departure city and to the same destination, with the lowest round-trip fares we found.