Cheapest return flights from Chicago to Orlando in July from $250

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

Return flights

23 Jul - 27 Jul Frontier Airlines direct
24 Jul - 27 Jul Frontier Airlines direct
06 Jul - 13 Jul Frontier Airlines direct
16 Jul - 20 Jul Frontier Airlines direct
03 Jul - 05 Jul Frontier Airlines direct
02 Jul - 05 Jul Frontier Airlines direct
09 Jul - 18 Jul Southwest Airlines direct
21 Jul - 28 Jul Southwest Airlines direct
17 Jul - 21 Jul Southwest Airlines direct
20 Jul - 23 Jul Southwest Airlines direct

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

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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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