Cheapest return flights from Orlando to Chicago in May from $112

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

Return flights

09 May - 16 May Spirit Airlines direct
07 May - 16 May Spirit Airlines direct
14 May - 18 May Frontier Airlines direct
30 May - 02 Jun Spirit Airlines direct
16 May - 26 May Spirit Airlines direct
12 May - 18 May Spirit Airlines direct
12 May - 16 May Spirit Airlines direct
12 May - 26 May Spirit Airlines direct
07 May - 18 May Spirit Airlines direct
07 May - 26 May Spirit Airlines direct
02 May - 18 May Spirit Airlines direct
16 May - 03 Jun Spirit Airlines direct
23 May - 03 Jun Spirit Airlines direct
13 May - 03 Jun Spirit Airlines direct
16 May - 02 Jun Spirit Airlines direct
23 May - 02 Jun Spirit Airlines direct
12 May - 02 Jun Spirit Airlines direct
18 May - 03 Jun Spirit Airlines direct
13 May - 02 Jun Spirit Airlines direct
26 May - 03 Jun Spirit Airlines direct

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

Powered by

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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.