Airlines with flights from Key West to Chicago

There are three airlines with scheduled flights between EYW and ORD. Both United and American Airlines operates non-stop flights from Key West International to Chicago O'Hare and the flight time is 3 hours and 25 minutes.

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Schedules

United Airlines

Non-stop with United Airlines

  • Total flight time: 3 hours and 25 minutes
  • Chicago is a United Airlines hub (Largest hub ).
  • 7 flights per week
  • Embraer 175 (Enhanced Winglets)
  • First class available
EYW
Direct
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
UA3499
16:00
16:00
16:00
16:00
16:00
16:00
16:00
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The timetable & schedule information was updated at 2026-04-21

American Airlines

Non-stop with American Airlines

  • Total flight time: 3 hours and 48 minutes
  • One World Alliance
  • Chicago is a American Airlines hub.
  • 7 flights per week
  • Embraer 170
  • First class available
EYW
Direct
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
AA3996
16:18
16:18
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AA3954
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16:56
16:56
16:56
16:56
16:58
SHOW RETURN SCHEDULE
CHECK PRICES FOR EYW - ORD

The timetable & schedule information was updated at 2026-04-21

American Airlines

Via Miami with American Airlines

  • Total flight time: 4h 50m - 7h 28m.
  • One World Alliance
  • Chicago is a American Airlines hub.
  • 107 flights per week
  • Embraer 170
EYW
 
Via MIA
 
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
AA3515
AA2400
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10:16
10:16
10:16
10:16
10:16
AA3515
AA2247
11:28
11:28
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AA3436
AA835
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11:30
11:30
11:30
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11:30
AA4646
AA835
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11:43
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AA3518
AA3056
13:38
13:38
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AA3577
AA3304
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13:41
13:41
13:41
13:41
AA2918
AA3304
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13:49
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AA3517
AA2323
19:40
19:40
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AA3438
AA483
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20:09
20:09
20:09
20:09
20:09
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CHECK PRICES FOR EYW - ORD

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Atlanta with Delta Air Lines

  • Total flight time: 5h 04m - 7h 17m.
  • Sky Team Alliance
  • 129 flights per week
EYW
 
Via ATL
 
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL1072
DL2894
07:45
07:45
07:45
07:45
07:45
07:45
07:45
DL1281
DL2738
11:56
11:56
11:56
11:56
11:56
11:49
11:56
DL1671
DL2879
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13:04
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DL1472
DL2879
14:24
14:24
14:24
14:24
14:24
14:24
14:24
DL2168
DL1199
18:18
18:18
18:18
18:18
18:18
18:18
18:18
SHOW RETURN SCHEDULE
CHECK PRICES FOR EYW - ORD

The timetable & schedule information was updated at 2026-04-21

American Airlines

Via Charlotte with American Airlines

  • Total flight time: 5h 06m - 7h 47m.
  • One World Alliance
  • Chicago is a American Airlines hub.
  • 89 flights per week
  • Embraer 170
EYW
 
Via CLT
 
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
AA1826
AA536
13:01
13:01
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AA3002
AA2488
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13:50
14:30
13:50
14:30
14:30
AA3519
AA627
16:40
16:40
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AA3822
AA815
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16:50
16:45
16:50
16:45
16:45
AA3432
AA627
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19:15
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19:15
19:15
AA2533
AA3014
19:29
19:29
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SHOW RETURN SCHEDULE
CHECK PRICES FOR EYW - ORD

The timetable & schedule information was updated at 2026-04-21

American Airlines

Via Washington with American Airlines

  • Total flight time: 5h 58m - 8h 08m.
  • One World Alliance
  • Chicago is a American Airlines hub.
  • 33 flights per week
  • Embraer 170
EYW
 
Via DCA
 
ORD
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
AA4389
AA1637
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12:06
12:06
12:06
12:06
12:06
AA4416
AA3254
12:07
12:07
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----
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SHOW RETURN SCHEDULE
CHECK PRICES FOR EYW - ORD

The timetable & schedule information was updated at 2026-04-21

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At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-07-13
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