Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 114 with Southwest Airlines.Best fare available on Aug 20, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

28 Jul
Frontier Airlines
07:45MCO
12:07MDW
1 StopUSD 198VIEW DEAL
29 Jul
Southwest Airlines
16:20MCO
19:15MDW
DirectUSD 176VIEW DEAL
30 Jul
Southwest Airlines
22:55MCO
01:45MDW
DirectUSD 209VIEW DEAL
3 Aug
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 153VIEW DEAL
3 Aug
Frontier Airlines
15:18MCO
23:03MDW
1 StopUSD 189VIEW DEAL
5 Aug
Frontier Airlines
13:45MCO
23:03MDW
1 StopUSD 147VIEW DEAL
6 Aug
Frontier Airlines
15:18MCO
23:03MDW
1 StopUSD 168VIEW DEAL
15 Aug
Frontier Airlines
07:45MCO
23:03MDW
1 StopUSD 125VIEW DEAL
19 Aug
Southwest Airlines
19:15MCO
22:00MDW
DirectUSD 129VIEW DEAL
20 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 114VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jul
from USD 176
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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