May is by far the best month, wherein you can get cheapest flights for Orlando to Chicago. Meanwhile, is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
Disclaimer - All the mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

Orlando
13:02
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
15:25
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
07:00
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
23:01
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
17:15
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
21:53
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
07:15
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
09:28
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
20:58
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
23:13
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
16:15
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
18:26
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
11:00
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
13:10
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
19:45
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
21:55
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
07:00
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
09:10
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
06:09
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
08:25
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026

Orlando
12:34
Orlando International Airport [MCO]
Sat , 16 May 2026

Chicago
14:40
Chicago O Hare International Airport [ORD]
Sat, 16 May 2026









