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Cheap flights from Orlando to Chicago

Find cheap Chicago to Orlando flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Orlando.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Orlando to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Orlando (ORL) - Chicago (CHI) 2024-05-29 2024-05-29 61 USD 5 hours 51 minutes Direct 2024-04-28T14:31:37
Orlando (ORL) - Chicago (CHI) 2024-05-22 2024-05-29 69 USD 5 hours 41 minutes Direct 2024-04-27T23:04:45
Orlando (ORL) - Chicago (CHI) 2024-05-18 2024-05-29 73 USD 5 hours 46 minutes Direct 2024-04-28T22:23:26
Orlando (ORL) - Chicago (CHI) 2024-05-29 2024-06-05 74 USD 5 hours 49 minutes Direct 2024-04-28T12:40:13
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-15 81 USD 5 hours 53 minutes Direct 2024-04-29T14:22:39
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-21 81 USD 5 hours 55 minutes Direct 2024-04-28T20:14:03
Orlando (ORL) - Chicago (CHI) 2024-05-18 2024-05-21 81 USD 5 hours 56 minutes Direct 2024-04-28T03:26:56
Orlando (ORL) - Chicago (CHI) 2024-05-18 2024-05-22 81 USD 5 hours 46 minutes Direct 2024-04-27T20:02:18
Orlando (ORL) - Chicago (CHI) 2024-05-22 2024-05-28 82 USD 5 hours 51 minutes Direct 2024-04-28T00:12:44
Orlando (ORL) - Chicago (CHI) 2024-05-23 2024-05-29 83 USD 5 hours 41 minutes Direct 2024-04-27T21:50:05
Orlando (ORL) - Chicago (CHI) 2024-05-29 2024-06-04 83 USD 5 hours 44 minutes Direct 2024-04-28T00:51:43
Orlando (ORL) - Chicago (CHI) 2024-05-29 2024-06-10 83 USD 5 hours 44 minutes Direct 2024-04-28T12:39:54
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-19 85 USD 5 hours 46 minutes Direct 2024-04-27T18:15:35
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-28 86 USD 5 hours 55 minutes Direct 2024-04-27T13:05:41
Orlando (ORL) - Chicago (CHI) 2024-05-18 2024-05-28 86 USD 5 hours 56 minutes Direct 2024-04-28T22:28:19
Orlando (ORL) - Chicago (CHI) 2024-08-15 2024-08-24 87 USD 5 hours 29 minutes Direct 2024-04-28T01:37:23
Orlando (ORL) - Chicago (CHI) 2024-08-15 2024-08-25 87 USD 5 hours 46 minutes Direct 2024-04-28T20:42:04
Orlando (ORL) - Chicago (CHI) 2024-08-17 2024-08-24 87 USD 5 hours 29 minutes Direct 2024-04-28T01:52:36
Orlando (ORL) - Chicago (CHI) 2024-08-17 2024-08-25 87 USD 5 hours 46 minutes Direct 2024-04-28T03:59:27
Orlando (ORL) - Chicago (CHI) 2024-08-17 2024-08-28 87 USD 5 hours 46 minutes Direct 2024-04-28T15:22:29
Orlando (ORL) - Chicago (CHI) 2024-08-24 2024-08-28 87 USD 5 hours 46 minutes Direct 2024-04-27T01:20:34
Orlando (ORL) - Chicago (CHI) 2024-05-16 2024-05-21 91 USD 5 hours 51 minutes Direct 2024-04-28T13:37:19
Orlando (ORL) - Chicago (CHI) 2024-05-16 2024-05-22 91 USD 5 hours 41 minutes Direct 2024-04-28T12:50:19
Orlando (ORL) - Chicago (CHI) 2024-05-22 2024-05-26 91 USD 5 hours 51 minutes Direct 2024-04-27T21:50:58
Orlando (ORL) - Chicago (CHI) 2024-05-22 2024-05-27 91 USD 5 hours 44 minutes Direct 2024-04-28T16:39:28
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-12 95 USD 5 hours 52 minutes Direct 2024-04-29T00:32:52
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-13 95 USD 5 hours 53 minutes Direct 2024-04-27T22:17:27
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-14 95 USD 5 hours 52 minutes Direct 2024-04-27T22:08:49
Orlando (ORL) - Chicago (CHI) 2024-05-11 2024-05-20 95 USD 5 hours 48 minutes Direct 2024-04-27T21:56:07
Orlando (ORL) - Chicago (CHI) 2024-05-16 2024-05-18 95 USD 5 hours 51 minutes Direct 2024-04-27T21:32:47

Orlando to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN2395 Orlando (MCO) Chicago (MDW) 9:35 p.m. 10:30 p.m. B737
WN565 Orlando (MCO) Chicago (MDW) 3:25 p.m. 6:55 p.m. B737
WN6191 Orlando (MCO) Chicago (MDW) 6:10 a.m. 8:05 a.m. B738
WN1987 Orlando (MCO) Chicago (MDW) 8:25 p.m. 12:20 a.m. B737
WN2164 Orlando (MCO) Chicago (MDW) 2:45 p.m. 6:05 p.m. B737
WN4610 Orlando (MCO) Chicago (MDW) 2:35 p.m. 4:55 p.m. B738
WN3423 Orlando (MCO) Chicago (MDW) 8:40 p.m. 9:55 p.m. B737
WN3313 Orlando (MCO) Chicago (MDW) 3:50 p.m. 5:40 p.m. B738
WN2985 Orlando (MCO) Chicago (MDW) 9:10 a.m. 1:05 p.m. B737
WN4104 Orlando (MCO) Chicago (MDW) 4:50 p.m. 6:05 p.m. B738
WN4404 Orlando (MCO) Chicago (MDW) 6:45 p.m. 9:35 p.m. B737
WN1664 Orlando (MCO) Chicago (MDW) 10:55 a.m. 2:05 p.m. B737
WN1456 Orlando (MCO) Chicago (MDW) 6 a.m. 8:35 a.m. B737
WN3496 Orlando (MCO) Chicago (MDW) 8:05 p.m. 12:45 a.m. B737
WN4259 Orlando (MCO) Chicago (MDW) 10:30 a.m. 11:50 a.m. B737
FR5033 Orlando (MCO) Chicago (MDW) 9:20 p.m. 10:15 p.m. 73H
WN59 Orlando (MCO) Chicago (MDW) 3:55 p.m. 8:55 p.m. B737
WN4827 Orlando (MCO) Chicago (MDW) 7:10 a.m. 8:25 a.m. B738
WN4302 Orlando (MCO) Chicago (MDW) 1:55 p.m. 3:40 p.m. B738
WN2692 Orlando (MCO) Chicago (MDW) 1:30 p.m. 2:50 p.m. B737
WN5704 Orlando (MCO) Chicago (MDW) 5 a.m. 6:35 a.m. B737
WN6817 Orlando (MCO) Chicago (MDW) 8:20 p.m. 9:50 p.m. B738
WN6313 Orlando (MCO) Chicago (MDW) 9:20 a.m. 9:35 a.m. B737
WN6773 Orlando (MCO) Chicago (MDW) 11:55 a.m. 1:40 p.m. B737
WN6432 Orlando (MCO) Chicago (MDW) 10:15 a.m. 11:10 a.m. B738
AX5030 Orlando (MCO) Chicago (MDW) 12:05 p.m. 2:10 p.m. ER4
BGM561 Orlando (MCO) Chicago (MDW) 9:05 p.m. 10:55 p.m. CR2
US2858 Orlando (MCO) Chicago (MDW) 2:10 p.m. 7:30 p.m. CR9
BR0696 Orlando (MCO) Chicago (MDW) 7:15 a.m. 10:45 a.m.
C31068 Orlando (MCO) Chicago (MDW) 9:25 p.m. 10:50 p.m.
FL223 Orlando (MCO) Chicago (MDW) 7:45 p.m. 9:35 p.m.

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