Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Orlando Chicago Midway | Outbound 04/29/25 direct WN3673 02h 50min | Return 05/08/25 direct F93854 02h 44min | | ![]() | ? | $197 | |
Orlando Chicago Midway | Outbound 06/18/25 1 Stopover (ATL) DL1494, DL1063 04h 39min | Return 07/15/25 1 Stopover (ATL) DL2307, DL1735 05h 06min | | ![]() | ? | $204 | |
Orlando Chicago Midway | Outbound 04/29/25 1 Stopover (ATL) F93507, F92143 20h 38min | Return 05/08/25 1 Stopover (ATL) F92292, F93976 21h 31min | | ![]() | ? | $234 | |
Orlando Chicago Midway | Outbound 06/18/25 1 Stopover (ATL) F93507, F92779 11h 44min | Return 07/15/25 1 Stopover (ATL) F92292, F93976 10h 18min | | ![]() | $332 | ||
Orlando Chicago Midway | Outbound 06/18/25 1 Stopover (ATL) F93507, F92779 11h 44min | Return 07/15/25 1 Stopover (ATL) F92292, F93976 10h 18min | | ![]() | $342 | ||
Orlando Chicago Midway | Outbound 06/18/25 3 Stopovers (MEX, CUN, GDL) Y40781, Y40118, Y41049, Y41840 26h 11min | Return 07/15/25 2 Stopovers (GDL, MEX) Y41841, Y40143, Y40780 18h 45min | | ![]() | ? | $970 |
Stops
- Direct flight
Airline
- Frontier Airlines
- Volaris
- Southwest Airlines
- Delta Air Lines
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 | $196.77 |
---|---|
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
- Flight Orlando - New York from $109
- Flight Orlando - Las Vegas from $201
- Flight Orlando - Miami from $158
- Flight Orlando - Los Angeles from $182
- Flight Orlando - Washington-DC from $78
- Flight Orlando - Atlanta from $69
- Flight Orlando - San Francisco from $207
- Flight Orlando - New York from $114
- Flight Orlando - Philadelphia from $111
- Flight Orlando - San Diego from $181
Alternative flights to Chicago Midway
- Flight San Francisco - Chicago Midway from $167
- Flight Boston - Chicago Midway from $172
- Flight Los Angeles - Chicago Midway from $185
- Flight Atlanta - Chicago Midway from $86
- Flight Washington DC - Chicago Midway from $216
- Flight Tampa - Chicago Midway from $235
- Flight Newark - Chicago Midway from $244
- Flight Minneapolis - Chicago Midway from $229
Flight destinations with a similar price
- Flight Orlando - Las Vegas from $201
- Flight Orlando - Los Angeles from $182
- Flight Orlando - San Francisco from $207
- Flight Orlando - San Diego from $181
- Flight Orlando - Denver from $201
- Flight Orlando - Kansas City from $200
- Flight Orlando - Montego Bay from $214
- Flight Orlando - San Jose, Costa Rica from $188