Cheapest return flights from Chicago to Orlando in June from $159

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

Return flights

12 Jun - 15 Jun Frontier Airlines direct
14 Jun - 19 Jun Frontier Airlines direct
05 Jun - 09 Jun Frontier Airlines
01 Jun - 04 Jun Frontier Airlines direct
15 Jun - 19 Jun Frontier Airlines direct
10 Jun - 14 Jun Frontier Airlines
08 Jun - 11 Jun Frontier Airlines direct
11 Jun - 18 Jun Frontier Airlines direct
15 Jun - 16 Jul Frontier Airlines direct
12 Jun - 19 Jun Frontier Airlines direct
03 Jun - 10 Jun Frontier Airlines
28 Jun - 03 Jul Frontier Airlines direct
28 Jun - 05 Jul Frontier Airlines direct
28 Jun - 01 Jul Southwest Airlines direct
27 Jun - 01 Jul Southwest Airlines
27 Jun - 03 Jul Southwest Airlines

Also check the deals for one-way flights from Chicago to Orlando 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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