Cheapest one-way flights from Toronto to Chicago in July from $90

AirHint found the following cheapest one-way flights from Toronto (YTZ) to Chicago (MDW) in July 2025 (see full year).

One-Way flights

20 Jul Porter Airlines (Canada) Ltd direct
24 Jul Porter Airlines (Canada) Ltd direct
26 Jul Porter Airlines (Canada) Ltd direct
22 Jul Porter Airlines (Canada) Ltd direct
23 Jul Porter Airlines (Canada) Ltd direct
25 Jul Porter Airlines (Canada) Ltd direct
29 Jul Porter Airlines (Canada) Ltd direct
21 Jul Porter Airlines (Canada) Ltd direct
19 Jul Porter Airlines (Canada) Ltd direct
28 Jul Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in July.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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