Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 99 with Frontier Airlines.Best fare available on Aug 24, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

20 Jul
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 156VIEW DEAL
20 Jul
Southwest Airlines
18:10MCO
21:10MDW
DirectUSD 188VIEW DEAL
23 Jul
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 184VIEW DEAL
24 Jul
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 184VIEW DEAL
25 Jul
Frontier Airlines
15:18MCO
23:03MDW
1 StopUSD 185VIEW DEAL
27 Jul
Allegiant Air
10:59MCO
15:38MDW
1 StopUSD 131VIEW DEAL
3 Aug
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 153VIEW DEAL
24 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 112VIEW DEAL
24 Aug
Frontier Airlines
10:03MCO
23:47MDW
1 StopUSD 99VIEW DEAL
24 Aug
Frontier Airlines
15:21MCO
23:47MDW
1 StopUSD 123VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jul
from USD 131
Aug
from USD 98
Sep
No flights
Oct
from USD 102
Nov
No flights
Dec
from USD 115

Airport Details

Origin

Orlando

Orlando International Airport (MCO)

Orlando, MCO
Zone

New York

Elev

96 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

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