Cheap flights from Toronto to Chicago from C$234 YHM, YTZ, YYZ → ORD

Found recently, and the cheapest we hold

What have prices looked like?

Over 48 days, 24 Sept to 11 Nov, the cheapest return we saw each day was C$247 (US$173) to C$564 (US$396).

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 27-night return fares leaving within 3 days of 8 Feb 2027 to compare.

Every date we hold

10 fares on 3 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from C$391 (US$274).

Found recently, and the cheapest we hold

What have prices looked like?

Over 46 days, 27 Sept to 11 Nov, the cheapest one-way we saw each day was C$188 (US$132) to C$379 (US$266).

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 20 Dec to compare.

Every date we hold

5 fares on 3 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from C$217 (US$152).

Return

Fares 14 to 29 days before departure were typically 27% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (48 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.

One-way

Fares 14 to 29 days before departure were typically 42% lower than 7 to 13 days before departure.

From the cheapest one-way each day between 27 Sept and 11 Nov (46 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.

How much is a return flight from Toronto to Chicago?

The cheapest return found recently is C$392 (US$275) with Porter Airlines Canada, 8 Feb 2027 to 7 Mar 2027, found 2 days ago. The cheapest return we hold, of any age, is C$391 (US$274) with Porter Airlines Canada, 26 Dec to 4 Jan 2027, found 5 days ago. The cheapest return fare on each of 3 departure dates is usually C$391 (US$275) to C$462 (US$324).

How much is a one-way flight from Toronto to Chicago?

The cheapest one-way found recently is C$234 (US$164) with Air Canada, 20 Dec, found 4 days ago. The cheapest one-way we hold, of any age, is C$217 (US$152) with Porter Airlines Canada, 13 Nov, found 5 days ago. The cheapest one-way fare on each of 3 departure dates is usually C$225 (US$158) to C$262 (US$184).

What is the cheapest month to fly from Toronto to Chicago?

December 2026 is the cheapest month for a return, from C$391 (US$274), 26 Dec to 4 Jan 2027, found 5 days ago. November 2026 is the cheapest month for a one-way, from C$217 (US$152), 13 Nov, found 5 days ago.

How far ahead should I book a flight from Toronto to Chicago?

In 48 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 27% lower than 0 to 6 days before departure. In 46 days of prices between 27 Sept and 11 Nov, one-way fares 14 to 29 days before departure were typically 42% lower than 7 to 13 days before departure.

Is there a direct flight from Toronto to Chicago?

Yes, the cheapest nonstop return found recently is C$392 (US$275) with Porter Airlines Canada, 8 Feb 2027 to 7 Mar 2027, found 2 days ago. The cheapest nonstop one-way found recently is C$234 (US$164) with Air Canada, 20 Dec, found 4 days ago.

How long is the flight from Toronto to Chicago?

The cheapest nonstop one-way found recently, with Air Canada on 20 Dec, takes 2 h 3 min from Pearson International Airport (YYZ) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Toronto to Chicago?

Between 22 Nov and 8 Feb 2027, Porter Airlines Canada has the cheapest return on all 3 departure dates we hold. Between 13 Nov and 19 Feb 2027, Porter Airlines Canada has the cheapest one-way on 2 of the 3 departure dates we hold, and Air Canada on 1.