Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 112 with Southwest Airlines.Best fare available on Aug 24, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

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
5 Aug
Southwest Airlines
07:40MCO
10:25MDW
DirectUSD 167VIEW 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
19 Aug
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 177VIEW DEAL
20 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 114VIEW DEAL
24 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 112VIEW DEAL

Orlando to Chicago monthly flight fare trend

Aug
from USD 98
Sep
from USD 114
Oct
from USD 102
Nov
No flights
Dec
from USD 115
Jan
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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