Best Flights starting from $85
from$85economy
Orlando (MCO)
Tue, Oct 27
One-way
Chicago (MDW)
—
from$85economy
Orlando (MCO)
Wed, Oct 28
One-way
Chicago (MDW)
—
from$100economy
Orlando (MCO)
Sat, Oct 24
One-way
Chicago (MDW)
—
from$100economy
Orlando (MCO)
Mon, Oct 26
One-way
Chicago (MDW)
—
from$100economy
Orlando (MCO)
Thu, Oct 29
One-way
Chicago (MDW)
—
from$200economy
Orlando (MCO)
Fri, Oct 23
One-way
Chicago (MDW)
—
from$200economy
Orlando (MCO)
Sun, Oct 25
One-way
Chicago (MDW)
—
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Orlando (MCO) to New York (Any) in October from $32
From $32
Orlando (MCO) to Washington, D.C. (Any) in October from $32
From $32
Orlando (MCO) to Washington, D.C. (IAD) in October from $54
From $54
Orlando (MCO) to New York (JFK) in October from $54
From $54
Orlando (MCO) to New York (LGA) in October from $54
From $54
Orlando (MCO) to Philadelphia (PHL) in October from $56
From $56
Flights from Other Cities
Mobile (MOB) to Chicago (MDW) in October from $165
From $165
Fort Lauderdale (Any) to Chicago (MDW) in October from $228
From $228
Tampa (Any) to Chicago (MDW) in October from $317
From $317
Mexico City (MEX) to Chicago (MDW) in October from $385
From $385
Sarasota (SRQ) to Chicago (MDW) in October from $435
From $435
Mobile (MOB) to Chicago (MDW) in November from $165
From $165