Cheap flights from Orlando to Chicago
From 124 USD — compare hundreds of airlines
Direct flightsCheapest: 2026-07 · 97 US$
Prices by date
97 US$
04/07
119 US$
05/07
119 US$
06/07
119 US$
07/07
119 US$
08/07
119 US$
09/07
119 US$
10/07
119 US$
11/07
141 US$
12/07
Airlines on this route
FAQ
What's the cheapest month to fly Orlando to Chicago?
Usually 2026-07, from 97 USD.
Are there direct flights from Orlando to Chicago?
We show both direct and connecting options — filter to compare.