Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 98 with Frontier Airlines.Best fare available on Aug 25, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

12 Jul
Frontier Airlines
15:18MCO
23:03MDW
1 StopUSD 151VIEW DEAL
14 Jul
Southwest Airlines
18:10MCO
21:10MDW
DirectUSD 105VIEW DEAL
14 Jul
Frontier Airlines
05:20MCO
12:07MDW
1 StopUSD 134VIEW DEAL
20 Jul
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 156VIEW DEAL
24 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 112VIEW DEAL
24 Aug
Frontier Airlines
10:03MCO
23:47MDW
1 StopUSD 99VIEW DEAL
25 Aug
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 102VIEW DEAL
25 Aug
Frontier Airlines
13:45MCO
23:47MDW
1 StopUSD 98VIEW DEAL
26 Aug
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 105VIEW DEAL
26 Aug
Frontier Airlines
13:45MCO
23:47MDW
1 StopUSD 98VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jul
from USD 105
Aug
from USD 98
Sep
No flights
Oct
from USD 102
Nov
No flights
Dec
No flights

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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