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 | | ![]() | ? | $200 | |
Orlando Chicago Midway | Outbound 10/18/25 direct F93853 02h 56min | Return 11/17/25 direct F93854 02h 41min | | ![]() | $210 | ||
Orlando Chicago Midway | Outbound 10/18/25 direct F93853 02h 56min | Return 11/17/25 direct F93854 02h 41min | | ![]() | $212 | ||
Orlando Chicago Midway | Outbound 10/18/25 direct F93853 02h 56min | Return 11/17/25 direct F93854 02h 41min | | ![]() | $222 | ||
Orlando Chicago Midway | Outbound 09/04/25 1 Stopover (DEN) F91733, F92210 18h 08min | Return 09/28/25 direct F93854 02h 41min | | ![]() | $260 | ||
Orlando Chicago Midway | Outbound 09/04/25 1 Stopover (DEN) F91733, F92210 18h 08min | Return 09/28/25 direct F93854 02h 41min | | ![]() | $271 | ||
Orlando Chicago Midway | Outbound 09/04/25 1 Stopover (ATL) F93507, F92291 06h 35min | Return 09/28/25 direct F93854 02h 41min | | ![]() | $307 | ||
Orlando Chicago Midway | Outbound 10/18/25 direct F93853 02h 56min | Return 11/17/25 direct F93854 02h 41min | | ![]() | ? | $666 |
Stops
- Direct flight
Airline
- Frontier Airlines
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
- Flight Orlando - New York from $127
- Flight Orlando - Las Vegas from $202
- Flight Orlando - Miami from $168
- Flight Orlando - Los Angeles from $182
- Flight Orlando - Washington-DC from $139
- Flight Orlando - Atlanta from $97
- Flight Orlando - San Francisco from $276
- Flight Orlando - New York from $155
- Flight Orlando - Philadelphia from $112
- Flight Orlando - San Diego from $239
Alternative flights to Chicago Midway
- Flight San Francisco - Chicago Midway from $290
- Flight Boston - Chicago Midway from $157
- Flight Los Angeles - Chicago Midway from $279
- Flight Atlanta - Chicago Midway from $86
- Flight Washington DC - Chicago Midway from $202
- Flight Tampa - Chicago Midway from $243
- Flight Newark - Chicago Midway from $212
- Flight Minneapolis - Chicago Midway from $213
Flight destinations with a similar price
- Flight Orlando - Las Vegas from $202
- Flight Orlando - Los Angeles from $182
- Flight Orlando - San Juan (Puerto Rico) from $184
- Flight Orlando - Aguadilla from $218