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

Return flights

12 Jun - 21 Jun	Porter Airlines (Canada) Ltd
14 Jun - 23 Jun	Delta
05 Jun - 27 Jun	Porter Airlines (Canada) Ltd
22 Jun - 10 Jul	Virgin Atlantic
06 Jun - 27 Jun	Virgin Atlantic
15 Jun - 11 Jul	Virgin Atlantic
14 Jun - 04 Jul	Air France
21 Jun - 27 Jun	Delta
22 Jun - 05 Jul	Air France

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

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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Cheapest return flights from Chicago to Madrid in June from $1099

Return flights