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

Find cheap airline tickets from Chicago to Key West by date

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  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • any
  • April 2019
  • May 2019
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  • October 2019
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  • February 2020
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  • price
  • month of departure
  • month of return
$312
Unknown Company outward: May 7, 2019
3:55p ORD » 12:10a EYW
Unknown Company 1 stop (8h15m)
Unknown Company inbound: May 14, 2019
10:30p EYW » 7:50p ORD
Unknown Company 1 stop (21h20m)
$339
Unknown Company outward: May 7, 2019
12:15p ORD » 3:40a EYW
Unknown Company 1 stop (15h25m)
Unknown Company inbound: May 14, 2019
9:40p EYW » 7:27a ORD
Unknown Company 1 stop (33h47m)
$349
Unknown Company outward: May 7, 2019
1:57p ORD » 12:10a EYW
Unknown Company 1 stop (10h13m)
Unknown Company inbound: May 14, 2019
5:25p EYW » 1:13a ORD
Unknown Company 1 stop (7h48m)
$349
American Airlines outward: May 7, 2019
8:30p ORD » 1:31a EYW
American Airlines 1 stop (5h01m)
American Airlines inbound: May 14, 2019
12:10p EYW » 4:11p ORD
American Airlines 1 stop (28h01m)
$354
Unknown Company outward: May 7, 2019
1:57p ORD » 12:10a EYW
Unknown Company 1 stop (10h13m)
Unknown Company inbound: May 14, 2019
10:30p EYW » 7:50p ORD
Unknown Company 1 stop (21h20m)
$367
Unknown Company outward: May 7, 2019
12:15p ORD » 3:40a EYW
Unknown Company 1 stop (15h25m)
Unknown Company inbound: May 15, 2019
12:40a EYW » 7:27a ORD
Unknown Company 1 stop (30h47m)
$383
American Airlines outward: May 7, 2019
8:30p ORD » 1:31a EYW
American Airlines 1 stop (5h01m)
American Airlines inbound: May 14, 2019
7:55p EYW » 4:11p ORD
American Airlines 1 stop (20h16m)
$383
Unknown Company outward: May 7, 2019
12:15p ORD » 12:10a EYW
Unknown Company 1 stop (11h55m)
Unknown Company inbound: May 15, 2019
12:40a EYW » 7:27a ORD
Unknown Company 1 stop (6h47m)
$385
Unknown Company outward: May 7, 2019
12:15p ORD » 3:40a EYW
Unknown Company 1 stop (15h25m)
Unknown Company inbound: May 15, 2019
12:40a EYW » 7:27a ORD
Unknown Company 1 stop (30h47m)
$386
Unknown Company outward: May 7, 2019
1:57p ORD » 3:40a EYW
Unknown Company 1 stop (13h43m)
JetBlue inbound: May 14, 2019
3:50p EYW » 5:48a ORD
JetBlue 1 stop (13h58m)
$410
Unknown Company outward: May 7, 2019
12:15p ORD » 3:40a EYW
Unknown Company 1 stop (15h25m)
Unknown Company inbound: May 15, 2019
12:40a EYW » 7:27a ORD
Unknown Company 1 stop (30h47m)
$424
Delta Air Lines outward: Jun 16, 2019
7:00p ORD » 1:41a EYW
Delta Air Lines 1 stop (6h41m)
Delta Air Lines inbound: Jun 25, 2019
11:05p EYW » 4:05a MDW
Delta Air Lines 1 stop (5h)
$424
Delta Air Lines outward: Jun 16, 2019
7:00p ORD » 1:41a EYW
Delta Air Lines 1 stop (6h41m)
Delta Air Lines inbound: Jun 25, 2019
11:05p EYW » 4:05a MDW
Delta Air Lines 1 stop (5h)
$443
Unknown Company outward: May 7, 2019
1:57p ORD » 3:40a EYW
Unknown Company 1 stop (13h43m)
Unknown Company inbound: May 14, 2019
9:40p EYW » 5:48a ORD
Unknown Company 1 stop (8h08m)
Return
Departure
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Airlines operating flights from Chicago to Key West

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Travel tips for flights Chicago - Key West

Average flight duration: 18h28m (flight with stopovers)

  • Arrival city:
  • Key West, USA
  • Airport(s):
  • Key West International Airport (EYW)
  • Local time:
  • Apr 18, 2019 10:26 PM, GMT-4
  • Weather:
  • min. 69ºF, max. 77ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Apr 18, 2019 9:26 PM, GMT-5
  • Weather:
  • min. 41ºF, max. 49ºF