Cheap flights from Chicago to Toronto from $149 MDW, ORD, RFD → YTZ, YYZ
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Toronto City Centre Airport (YTZ), Pearson International Airport (YYZ)
The cheapest return found recently is $641 with Frontier Airlines, 30 Dec – 20 Jan 2027, found 3 days ago. The cheapest one-way found recently is $149 with Air Canada, 23 May 2027, found yesterday.
- Cheapest one-way found recently
- $149, Air Canada, found yesterday
- Cheapest return found recently
- $641, 30 Dec to 20 Jan 2027
- Cheapest month to fly
- November 2026, one-way fares from $115 found in the last 7 days
- Airlines with nonstop flights
- Porter Airlines, American Airlines, Air Canada
- Shortest nonstop flight found
- 1 h 41 min
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$641
30 Dec – 20 Jan 2027 · Frontier Airlines
Chicago Midway International Airport (MDW) → Pearson International Airport (YYZ)
Leaves 8:35 p.m. · Return leaves 6:30 p.m. · 42 h 17 min of travel, both ways together
out 1 stop, back 2 stops
found 3 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$641 30 Dec – 20 Jan 2027found 3 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 49 days, 24 Sept to 12 Nov, the cheapest return we saw each day was $213 to $641.
At $641, the cheapest return found recently is at the high end of that range.
Those were the prices on those days, not today's.
Is this a good return price?
Not enough comparable prices yet: we hold return fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 21-night return fares leaving within 3 days of 30 Dec to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 30 Dec – 20 Jan 2027 | $641 | Frontier Airlines | Chicago Midway International Airport (MDW) → Pearson International Airport (YYZ) | out 1 stop, back 2 stops | found 3 days ago | See prices for these dates |
Airlines on the cheapest dates: Frontier Airlines.
One-way
The cheapest one-way fare on each of 5 departure dates is usually $129 to $149.
Cheapest one-way found recently
$149
23 May 2027 · Air Canada
O'Hare International Airport (ORD) → Toronto City Centre Airport (YTZ)
Leaves 2:00 p.m. · 1 h 41 min trip
nonstop
found yesterday
Cheapest nonstop one-way
$149
23 May 2027 · Air Canada
O'Hare International Airport (ORD) → Toronto City Centre Airport (YTZ)
Leaves 2:00 p.m. · 1 h 41 min trip
nonstop
found yesterday
Found recently, and the cheapest we hold
$149 23 May 2027found yesterdayOpen this trip
$115 14 Novfound 2 days agoOpen this trip
What have prices looked like?
Over 49 days, 24 Sept to 12 Nov, the cheapest one-way we saw each day was $81 to $220.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 5 departure dates from 14 Nov to 23 May 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 23 May 2027 to compare.
Every date we hold
7 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 14 Nov | $115 | American Airlines | O'Hare International Airport (ORD) → Pearson International Airport (YYZ) | nonstop | found 2 days ago | Open this trip |
| 16 Nov | $219 | Air Canada | O'Hare International Airport (ORD) → Pearson International Airport (YYZ) | stops unknown | found 3 days ago | Open this trip |
| 18 Dec | $129 | Porter Airlines Canada | O'Hare International Airport (ORD) → Toronto City Centre Airport (YTZ) | nonstop | found 2 days ago | Open this trip |
| 15 Apr 2027 | $134 | Porter Airlines Canada | O'Hare International Airport (ORD) → Toronto City Centre Airport (YTZ) | nonstop | found 2 days ago | Open this trip |
| 23 May 2027 | $149 | Air Canada | O'Hare International Airport (ORD) → Toronto City Centre Airport (YTZ) | nonstop | found yesterday | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $115.
Airlines on the cheapest dates: Air Canada, Porter Airlines Canada, American Airlines.
Premium cabin fares from Chicago to Toronto
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 30 Dec – 20 Jan 2027 in another cabin: Premium economy · Business · First
Today's prices for 23 May 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Toronto?
Return
Fares 14 to 29 days before departure were typically 16% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 12 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $352 | $306 | +19% | 26 |
| 7–13 days | $347 | $251 | +17% | 30 |
| 14–29 days | $296 | $213 | Cheapest seen | 41 |
| 30–59 days | $321 | $296 | +8% | 31 |
| 60–89 days | $398 | $296 | +35% | 13 |
| 90–179 days | $400 | $349 | +35% | 16 |
| 180+ days | $413 | $292 | +40% | 24 |
One-way
The cheapest fares were 7 to 13 days before departure.
From the cheapest one-way each day between 24 Sept and 12 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $113 | $83 | +2% | 22 |
| 7–13 days | $111 | $81 | Cheapest seen | 15 |
| 14–29 days | $152 | $96 | +37% | 21 |
| 30–59 days | $193 | $85 | +74% | 20 |
| 60–89 days | $186 | $82 | +68% | 18 |
| 90–179 days | $156 | $134 | +41% | 34 |
| 180+ days | $186 | $149 | +68% | 9 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
One-way
Chicago → Buffalo
95 km from Toronto
$100
$49 less than flying to Toronto
23 Nov · ORD → BUF · nonstop
found today
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 30 Dec – 20 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Chicago to Toronto?
The cheapest return found recently is $641 with Frontier Airlines, 30 Dec to 20 Jan 2027, found 3 days ago.
How much is a one-way flight from Chicago to Toronto?
The cheapest one-way found recently is $149 with Air Canada, 23 May 2027, found yesterday. The cheapest one-way we hold, of any age, is $115 with American Airlines, 14 Nov, found 2 days ago. The cheapest one-way fare on each of 5 departure dates is usually $129 to $149.
What is the cheapest month to fly from Chicago to Toronto?
November 2026 is the cheapest month for a one-way, from $115, 14 Nov, found 2 days ago.
How far ahead should I book a flight from Chicago to Toronto?
In 49 days of prices between 24 Sept and 12 Nov, return fares 14 to 29 days before departure were typically 16% lower than 0 to 6 days before departure. One-way fares were cheapest 7 to 13 days before departure.
Is there a direct flight from Chicago to Toronto?
Yes, the cheapest nonstop one-way found recently is $149 with Air Canada, 23 May 2027, found yesterday.
How long is the flight from Chicago to Toronto?
The cheapest nonstop one-way found recently, with Air Canada on 23 May 2027, takes 1 h 41 min from O'Hare International Airport (ORD) to Toronto City Centre Airport (YTZ).
Which airlines have the cheapest flights from Chicago to Toronto?
Between 14 Nov and 23 May 2027, Air Canada has the cheapest one-way on 2 of the 5 departure dates we hold, Porter Airlines Canada on 2 and American Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work