Toronto to Chicago YHM, YTZ, YYZ → MDW, ORD
Hamilton Airport (YHM), Toronto City Centre Airport (YTZ), Pearson International Airport (YYZ) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is C$532 (US$376) with Porter Airlines Canada, 23 Oct – 3 Nov, found yesterday. The cheapest one-way found recently is C$242 (US$171) with Porter Airlines Canada, 20 Nov, found 3 days ago.
Return
The cheapest return fare on each of 4 departure dates is usually C$394 (US$278) to C$1,175 (US$830).
Cheapest return found recently
C$532 (US$376)
23 Oct – 3 Nov · Porter Airlines Canada
Toronto City Centre Airport (YTZ) → Chicago Midway International Airport (MDW)
Leaves 10:10 a.m. · Return leaves 12:15 p.m. · 3 h 35 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Cheapest nonstop return
C$532 (US$376)
23 Oct – 3 Nov · Porter Airlines Canada
Toronto City Centre Airport (YTZ) → Chicago Midway International Airport (MDW)
Leaves 10:10 a.m. · Return leaves 12:15 p.m. · 3 h 35 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Found recently, and the cheapest we hold
C$532 (US$376) 23 Oct – 3 Novfound yesterdaySee prices for these dates
C$386 (US$273) 7 Nov – 8 Novfound 4 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was C$245 (US$173) to C$555 (US$392).
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 4 departure dates from 23 Oct to 13 Nov, 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 11-night return fares leaving within 3 days of 23 Oct to compare.
Every date we hold
8 fares on 4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Oct – 3 Nov | C$532 (US$376) | Porter Airlines Canada | Toronto City Centre Airport (YTZ) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 30 Oct – 2 Nov | C$3,104 (US$2,193) | Porter Airlines Canada | Hamilton Airport (YHM) → Chicago Midway International Airport (MDW) | out 3 stops, back 4 stops | found 4 days ago | See prices for these dates |
| 7 Nov – 8 Nov | C$386 (US$273) | United Airlines | Pearson International Airport (YYZ) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
| 13 Nov – 16 Nov | C$396 (US$280) | Porter Airlines Canada | Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from C$386 (US$273).
Airlines on the cheapest dates: Porter Airlines Canada, United Airlines.
One-way
The cheapest one-way fare on each of 5 departure dates is usually C$242 (US$171) to C$242 (US$171).
Cheapest one-way found recently
C$242 (US$171)
20 Nov · Porter Airlines Canada
Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD)
Leaves 10:30 a.m. · 2 h 5 min trip
nonstop
found 3 days ago
Cheapest nonstop one-way
C$242 (US$171)
20 Nov · Porter Airlines Canada
Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD)
Leaves 10:30 a.m. · 2 h 5 min trip
nonstop
found 3 days ago
Found recently, and the cheapest we hold
C$242 (US$171) 20 Novfound 3 days agoOpen this trip
C$231 (US$163) 8 Novfound 6 days agoOpen this trip
What have prices looked like?
Over 22 days, 27 Sept to 18 Oct, the cheapest one-way we saw each day was C$231 (US$163) to C$330 (US$233).
22 days is a short history, so treat this range as an early guide.
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 20 Oct to 23 Nov, 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?
No. We hold one-way fares on 2 other departure dates within 3 days of 20 Nov, and none is cheaper.
Every date we hold
10 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 20 Oct | C$259 (US$183) | American Airlines | Pearson International Airport (YYZ) → O'Hare International Airport (ORD) | stops unknown | found 3 days ago | Open this trip |
| 8 Nov | C$231 (US$163) | Porter Airlines Canada | Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
| 20 Nov | C$242 (US$171) | Porter Airlines Canada | Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 22 Nov | C$242 (US$171) | Air Canada | Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 23 Nov | C$242 (US$171) | Air Canada | Toronto City Centre Airport (YTZ) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from C$231 (US$163).
Airlines on the cheapest dates: Porter Airlines Canada, Air Canada, American Airlines.
Premium cabin fares from Toronto to Chicago
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 23 Oct – 3 Nov in another cabin: Premium economy · Business · First
Today's prices for 20 Nov in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Toronto to Chicago?
Return
Fares 30 to 59 days before departure were typically 27% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 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 | C$531 (US$375) | C$459 (US$324) | +37% | 16 |
| 7–13 days | C$531 (US$375) | C$245 (US$173) | +37% | 19 |
| 14–29 days | C$457 (US$323) | C$386 (US$273) | +18% | 8 |
| 30–59 days | C$389 (US$275) | C$384 (US$271) | Cheapest seen | 16 |
| 90–179 days | C$538 (US$380) | C$538 (US$380) | +38% | 10 |
One-way
The cheapest fares were 30 to 59 days before departure.
From the cheapest one-way each day between 27 Sept and 18 Oct (22 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 |
|---|---|---|---|---|
| 30–59 days | C$247 (US$175) | C$242 (US$171) | Cheapest seen | 10 |
| 60–89 days | C$330 (US$233) | C$330 (US$233) | +34% | 8 |
| 180+ days | C$300 (US$212) | C$300 (US$212) | +22% | 8 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
One-way
Buffalo → Chicago
95 km from Toronto
C$323 (US$228)
C$81 (US$57) more than flying from Toronto
14 Nov · BUF → ORD · 2 stops
found 2 days ago
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 23 Oct – 3 Nov. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days: the price the seller showed on Aviasales; bags may cost extra. Canadian dollars at the Bank of Canada rate of 2026-10-16, US dollars in brackets. Fares change, so check today's price before you book. How our prices work