Cheapest return flights from Orlando to Chicago in June from $210

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

Return flights

04 Jun - 08 Jun Frontier Airlines direct
11 Jun - 15 Jun Frontier Airlines direct
15 Jun - 19 Jun Frontier Airlines direct
06 Jun - 12 Jun Allegiant Air
29 Jun - 30 Jun Southwest Airlines direct
12 Jun - 17 Jun Southwest Airlines direct
10 Jun - 13 Jun Frontier Airlines

Also check the deals for one-way flights from Orlando 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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