Take off on cheap flights from Orlando to Chicago, your adventure starts now!

Find cheap airline tickets from Orlando to Chicago by date

  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • price
  • month of departure
  • month of return
$200
Frontier Airlines outward: May 4, 2021
3:18a MCO » 6:36a ORD
Frontier Airlines direct (3h18m)
Frontier Airlines inbound: May 6, 2021
11:39p ORD » 2:26a MCO
Frontier Airlines direct (2h47m)
$209
American Airlines outward: Dec 21, 2020
1:00p MCO » 3:58p ORD
American Airlines direct (2h58m)
United Airlines inbound: Dec 26, 2020
1:00p ORD » 7:06p MCO
United Airlines 1 stop (6h06m)
$228
Allegiant Air outward: Dec 20, 2020
7:51p SFB » 10:36p RFD
Allegiant Air direct (2h45m)
United Airlines inbound: Dec 26, 2020
1:00p ORD » 7:06p MCO
United Airlines 1 stop (6h06m)
$288
United Airlines outward: Jun 1, 2021
9:35p MCO » 4:11a ORD
United Airlines 1 stop (6h36m)
Unknown Company inbound: Jun 3, 2021
3:56p ORD » 1:14a MCO
Unknown Company 1 stop (9h18m)
$306
United Airlines outward: May 31, 2021
2:30p MCO » 5:29p ORD
United Airlines direct (2h59m)
Unknown Company inbound: Jun 3, 2021
3:56p ORD » 1:14a MCO
Unknown Company 1 stop (9h18m)
$306
United Airlines outward: May 31, 2021
2:30p MCO » 5:29p ORD
United Airlines direct (2h59m)
Unknown Company inbound: Jun 3, 2021
3:56p ORD » 1:14a MCO
Unknown Company 1 stop (9h18m)
$315
United Airlines outward: Jun 8, 2021
2:50a MCO » 5:49a ORD
United Airlines direct (2h59m)
United Airlines inbound: Jun 10, 2021
5:01p ORD » 7:39p MCO
United Airlines direct (2h38m)
$332
United Airlines outward: Jun 4, 2021
3:40p MCO » 8:42p ORD
United Airlines 1 stop (5h02m)
United Airlines inbound: Jun 6, 2021
4:04p ORD » 10:30p MCO
United Airlines 1 stop (6h26m)
$365
United Airlines outward: Jun 4, 2021
2:30p MCO » 5:29p ORD
United Airlines direct (2h59m)
Unknown Company inbound: Jun 6, 2021
3:30p ORD » 7:11p MCO
Unknown Company 1 stop (27h41m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest Orlando Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Orlando - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Orlando to Chicago

  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • all
  • American Airlines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Dec 21, 2020
Spirit Airlines direct
return: Dec 26, 2020
Spirit Airlines 1 stop
Frontier Airlines
outbound: May 3, 2021
Frontier Airlines direct
return: May 6, 2021
Frontier Airlines direct
American Airlines
outbound: Dec 21, 2020
American Airlines direct
return: Dec 26, 2020
United Airlines 1 stop
United Airlines
outbound: Jun 1, 2021
United Airlines 1 stop
return: Jun 3, 2021
United Airlines 1 stop

Travel tips for flights Orlando - Chicago

Average flight duration: 2h51m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 20, 2020 8:55 PM, GMT-5
  • Weather:
  • min. 47ºF, max. 62ºF
  • Departure city:
  • Orlando, USA
  • Airport(s):
  • Orlando Executive Airport (ORL)
  • Orlando International Airport (MCO)
  • Sanford International Airport (SFB)
  • Local time:
  • Oct 20, 2020 9:55 PM, GMT-4
  • Weather:
  • min. 74ºF, max. 81ºF