Cheapest return flights from Toronto to Chicago in June from $294

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

Return flights

19 Jun - 21 Jun Porter Airlines (Canada) Ltd direct
18 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
19 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
22 Jun - 27 Jun Porter Airlines (Canada) Ltd direct
22 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
23 Jun - 27 Jun Porter Airlines (Canada) Ltd direct
14 Jun - 27 Jun Porter Airlines (Canada) Ltd direct
14 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
08 Jun - 27 Jun Porter Airlines (Canada) Ltd direct
08 Jun - 22 Jun Porter Airlines (Canada) Ltd direct
22 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
22 Jun - 11 Jul Porter Airlines (Canada) Ltd direct
23 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
23 Jun - 11 Jul Porter Airlines (Canada) Ltd direct
14 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
27 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
27 Jun - 11 Jul Porter Airlines (Canada) Ltd direct
19 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
18 Jun - 04 Jul Porter Airlines (Canada) Ltd direct
22 Jun - 05 Jul 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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