Cheapest one-way flights from Orlando to Chicago in June from $129

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

One-Way flights

01 Jun Frontier Airlines direct
08 Jun Frontier Airlines direct
18 Jun Frontier Airlines direct
19 Jun Frontier Airlines direct
15 Jun Frontier Airlines direct
14 Jun Frontier Airlines direct
07 Jun Frontier Airlines direct
17 Jun Southwest Airlines direct
26 Jun Southwest Airlines
26 Jun Southwest Airlines direct

Also check the deals for return 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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