Flights from Orlando to Chicago

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Outbound flight: 03/14/21
09:00 MCO
10:58 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/28/21
18:25 CHI
23:58 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$309
Check
Outbound flight: 03/14/21
09:00 MCO
10:58 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/28/21
18:25 CHI
23:58 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$309
Check
Outbound flight: 03/14/21
07:00 MCO
08:58 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/28/21
18:25 CHI
23:58 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$309
Check
Outbound flight: 03/14/21
05:02 MCO
08:33 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 03/28/21
18:25 CHI
23:58 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$310
Check
Outbound flight: 03/14/21
05:02 MCO
08:33 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 03/28/21
18:25 CHI
23:58 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$310
Check
Outbound flight: 03/14/21
08:30 MCO
10:29 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 03/28/21
05:20 CHI
11:32 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$334
Check
Outbound flight: 03/14/21
09:35 MCO
11:35 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 03/28/21
18:15 CHI
21:55 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
direct
United Airlines
$370
Check
Outbound flight: 03/14/21
07:00 MCO
09:00 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 03/28/21
18:15 CHI
21:55 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
direct
United Airlines
$370
Check
Outbound flight: 03/14/21
07:00 MCO
09:00 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 03/28/21
18:15 CHI
21:55 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
direct
United Airlines
$370
Check
Outbound flight: 03/14/21
08:20 MCO
14:00 CHI
Orlando International Airport, FL
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 03/28/21
05:20 CHI
11:32 MCO
Chicago-IL all Airports (ORD, MDW, RFD)
Orlando International Airport, FL
1 Stopover
American Airlines
$418
Check
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

Favorite airline: United Airlines
United Airlines is the most popular airline for flights from Orlando to Chicago.
United Airlines
15 %
Spirit Airlines
12 %
Frontier Airlines
7 %
Direct flights are cheaper
On this route, direct flights are $25.00 cheaper than flights with a stopover.
non stop flight
1 stop
03h 07min
05h 22min
$44
$69
The favorite connection is non-stop
Flights from Orlando to Chicago are most often booked as a direct flight.
Route
bookings
Direct flights
03h 07min, from $44
46 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
08h 29min, from $79
23 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
05h 22min, from $69
11 %
Flight information Orlando - Chicago
Alternative flight routes
Cheap direct flights
Flight details Orlando - Chicago
  • Flight duration: min. 02:45 / max. 11:20
  • Distance: 1603 km
  • Flights per week: 237
  • Return flight duration: min. 02:30 / max. 12:55
Top Flight Routes
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.