Flights from Orlando to Chicago Midway

Our cheapest offers for flights from Orlando to Chicago Midway

Here you can compare cheap flights from Orlando (MCO) to Chicago Midway (MDW) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago Midway. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Orlando
Chicago Midway
Outbound
10/18/25
direct
F93853
02h 56min
Return
11/17/25
direct
F93854
02h 41min
Frontier Airlines ?
$200
Orlando
Chicago Midway
Outbound
10/18/25
direct
F93853
02h 56min
Return
11/17/25
direct
F93854
02h 41min
Frontier Airlines
$210
Orlando
Chicago Midway
Outbound
10/18/25
direct
F93853
02h 56min
Return
11/17/25
direct
F93854
02h 41min
Frontier Airlines
$212
Orlando
Chicago Midway
Outbound
10/18/25
direct
F93853
02h 56min
Return
11/17/25
direct
F93854
02h 41min
Frontier Airlines
$222
Orlando
Chicago Midway
Outbound
09/04/25
1 Stopover (DEN)
F91733, F92210
18h 08min
Return
09/28/25
direct
F93854
02h 41min
Frontier Airlines
$260
Orlando
Chicago Midway
Outbound
09/04/25
1 Stopover (DEN)
F91733, F92210
18h 08min
Return
09/28/25
direct
F93854
02h 41min
Frontier Airlines
$271
Orlando
Chicago Midway
Outbound
09/04/25
1 Stopover (ATL)
F93507, F92291
06h 35min
Return
09/28/25
direct
F93854
02h 41min
Frontier Airlines
$307
Orlando
Chicago Midway
Outbound
10/18/25
direct
F93853
02h 56min
Return
11/17/25
direct
F93854
02h 41min
Frontier Airlines ?
$666
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Orlando to Chicago Midway

Favorite airline: Frontier Airlines
80 % of flights from Orlando to Chicago Midway are booked with Frontier Airlines.
Frontier Airlines
80 %
Delta
20 %
Direct flights are the cheapest connection
Compared to flights with a stopover, direct flights are $114.00 cheaper on this route.
non stop flight
1 stop
02h 47min
25h 26min
$84
$198
The favorite connection is non-stop
57 % of all bookings on the route Orlando to Chicago Midway are for non-stop flights.
Route
bookings
Direct flights
02h 47min, from $84
57 %
1 stopover Denver International Airport, CO
25h 26min, from $198
29 %
1 stopover Philadelphia International Airport, PA
06h 06min, from $606
14 %

Important flight information

Flight information: Orlando - Chicago Midway

Roundtrip from $199.48
Flight duration min. 02:45 / max. 11:20
Return flight duration min. 02:30/ max. 12:55
Distance 1597 km
Flights per week 115
Departure airport Airport Orlando International Airport, FL (MCO)
Arrival airport Airport Chicago Midway International Airport, IL (MDW)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Chicago Midway
Flight destinations with a similar price