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Cheap flights from Chicago to Orlando

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

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

Chicago to Orlando flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Chicago (CHI) - Orlando (ORL) 2026-11-17 2026-11-20 150 USD 20 hours 20 minutes Connection 2026-11-05T20:46:45
Chicago (CHI) - Orlando (ORL) 2027-01-09 2027-01-17 157 USD 15 hours 29 minutes Connection 2026-11-08T16:31:58
Chicago (CHI) - Orlando (ORL) 2027-03-21 2027-03-27 179 USD 9 hours 53 minutes Connection 2026-11-06T14:49:23
Chicago (CHI) - Orlando (ORL) 2027-01-22 2027-01-29 196 USD 18 hours 3 minutes Connection 2026-11-10T11:30:22
Chicago (CHI) - Orlando (ORL) 2027-01-07 2027-01-12 204 USD 11 hours 54 minutes Connection 2026-11-12T01:41:09
Chicago (CHI) - Orlando (ORL) 2026-12-01 2026-12-04 206 USD 17 hours 7 minutes Connection 2026-11-11T20:46:10
Chicago (CHI) - Orlando (ORL) 2026-12-11 2026-12-14 214 USD 5 hours 51 minutes Direct 2026-11-11T15:03:02
Chicago (CHI) - Orlando (ORL) 2027-02-10 2027-02-14 216 USD 10 hours 31 minutes Connection 2026-11-11T20:50:01
Chicago (CHI) - Orlando (ORL) 2026-12-10 2026-12-13 249 USD 6 hours 50 minutes Direct 2026-11-05T16:50:59
Chicago (CHI) - Orlando (ORL) 2026-11-27 2026-11-29 255 USD 11 hours 15 minutes Connection 2026-11-11T15:08:58
Chicago (CHI) - Orlando (ORL) 2026-11-20 2026-11-22 257 USD 5 hours 44 minutes Direct 2026-11-05T16:21:28
Chicago (CHI) - Orlando (ORL) 2026-11-20 2026-11-23 257 USD 5 hours 44 minutes Direct 2026-11-05T16:22:06
Chicago (CHI) - Orlando (ORL) 2026-12-03 2026-12-06 258 USD 10 hours 41 minutes Connection 2026-11-06T17:59:49
Chicago (CHI) - Orlando (ORL) 2026-12-11 2026-12-13 267 USD 10 hours 45 minutes Connection 2026-11-06T14:42:32
Chicago (CHI) - Orlando (ORL) 2027-03-01 2027-03-08 299 USD 5 hours 51 minutes Direct 2026-11-11T20:48:03
Chicago (CHI) - Orlando (ORL) 2026-12-24 2026-12-27 310 USD 13 hours 5 minutes Connection 2026-11-09T06:15:30
Chicago (CHI) - Orlando (ORL) 2026-11-26 2026-11-30 325 USD 10 hours 11 minutes Connection 2026-11-07T05:38:53
Chicago (CHI) - Orlando (ORL) 2026-11-13 2026-11-16 326 USD 18 hours 15 minutes Connection 2026-11-09T23:37:22
Chicago (CHI) - Orlando (ORL) 2026-11-26 2026-11-28 392 USD 10 hours 11 minutes Connection 2026-11-11T20:49:07
Chicago (CHI) - Orlando (ORL) 2027-04-03 2027-04-10 395 USD 8 hours 0 minutes Direct 2026-11-11T20:47:42
Chicago (CHI) - Orlando (ORL) 2026-11-26 2026-11-29 455 USD 13 hours 40 minutes Connection 2026-11-11T20:48:42
Chicago (CHI) - Orlando (ORL) 2026-11-25 2026-11-29 460 USD 5 hours 44 minutes Direct 2026-11-09T00:23:24

Chicago to Orlando flight status

Flight Origin Destination Departure Arrival Equip
WN727 Chicago (MDW) Orlando (MCO) 5:25 a.m. 7 a.m. B737
WN2215 Chicago (MDW) Orlando (MCO) 7:15 a.m. 10:35 a.m. B738
WN3082 Chicago (MDW) Orlando (MCO) 7:40 p.m. 9:05 p.m. B737
WN4304 Chicago (MDW) Orlando (MCO) 3:10 p.m. 8:30 p.m. B738
WN3738 Chicago (MDW) Orlando (MCO) 7:25 a.m. 8:55 a.m. B737
WN4547 Chicago (MDW) Orlando (MCO) 6:10 a.m. 7:25 a.m. B737
WN4076 Chicago (MDW) Orlando (MCO) 10:50 a.m. 12:05 p.m. B737
WN4145 Chicago (MDW) Orlando (MCO) 5 a.m. 6:55 a.m. B738
WN2697 Chicago (MDW) Orlando (MCO) 6:25 p.m. 7:55 p.m. B738
WN2352 Chicago (MDW) Orlando (MCO) 8:10 p.m. 9:40 p.m. B737
WN1628 Chicago (MDW) Orlando (MCO) 6 a.m. 7:10 a.m. B737
WN2330 Chicago (MDW) Orlando (MCO) 7:15 p.m. 8:30 p.m. B737
WN2680 Chicago (MDW) Orlando (MCO) 9:40 a.m. 11:35 a.m. B737
WN4746 Chicago (MDW) Orlando (MCO) 5:30 p.m. 7:20 p.m. B737
WN1575 Chicago (MDW) Orlando (MCO) 6:30 p.m. 10:45 p.m. B737
WN1206 Chicago (MDW) Orlando (MCO) 6:35 a.m. 8:05 a.m. B737
WN1023 Chicago (MDW) Orlando (MCO) 11:55 a.m. 3:25 p.m. B737
WN6822 Chicago (MDW) Orlando (MCO) noon 1:40 p.m.
WN5187 Chicago (MDW) Orlando (MCO) 1:45 p.m. 5:10 p.m. B738
WN6907 Chicago (MDW) Orlando (MCO) 2:40 p.m. 5:50 p.m. B737
WN5935 Chicago (MDW) Orlando (MCO) 6:45 a.m. 8 a.m. B737
WN5664 Chicago (MDW) Orlando (MCO) 12:20 p.m. 8:15 p.m. B737
WN6941 Chicago (MDW) Orlando (MCO) 12:15 p.m. 2:30 p.m. B737
WN6774 Chicago (MDW) Orlando (MCO) 2:25 p.m. 6 p.m. B737
FL445 Chicago (MDW) Orlando (MCO) 7:35 a.m. 9:25 a.m.
AI44 Chicago (MDW) Orlando (MCO) 1:25 p.m. 3:15 p.m.
US2076 Chicago (MDW) Orlando (MCO) 6:40 p.m. 10:10 p.m. 319
FL263 Chicago (MDW) Orlando (MCO) 2:30 p.m. 6:05 p.m.
JG1756 Chicago (MDW) Orlando (MCO) 6:50 a.m. 11:25 a.m. AT7
FL2 Chicago (MDW) Orlando (MCO) 3:50 p.m. 5 p.m. 717
A53346 Chicago (MDW) Orlando (MCO) 6 a.m. 9:40 a.m. AT7

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