Cheapest return flights from Toronto to Chicago in June from $330

AirHint found the following cheapest return flights from Toronto (YTZ) to Chicago (MDW) in June 2026 (see full year).

Return flights

04 Jun - 07 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 18 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 20 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 17 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 23 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 24 Jun Porter Airlines (Canada) Ltd direct
25 Jun - 08 Jul Porter Airlines (Canada) Ltd direct
25 Jun - 16 Jul Porter Airlines (Canada) Ltd direct
25 Jun - 14 Jul Porter Airlines (Canada) Ltd direct
25 Jun - 11 Jul Porter Airlines (Canada) Ltd direct
17 Jun - 08 Jul Porter Airlines (Canada) Ltd direct
20 Jun - 08 Jul Porter Airlines (Canada) Ltd direct
20 Jun - 11 Jul Porter Airlines (Canada) Ltd direct
19 Jun - 08 Jul Porter Airlines (Canada) Ltd direct
25 Jun - 06 Jul Porter Airlines (Canada) Ltd direct
17 Jun - 06 Jul Porter Airlines (Canada) Ltd direct
04 Jun - 21 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 19 Jun Porter Airlines (Canada) Ltd direct
04 Jun - 10 Jun Porter Airlines (Canada) Ltd direct

Also check the deals for one-way flights from Toronto to Chicago in June.

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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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