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

  • any
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • any
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • price
  • month of departure
  • month of return
$337
outward: Jul 10, 2019
2:02p ORD » 2:20a EYW
Unknown Company 1 stop (12h18m)
inbound: Jul 14, 2019
12:20a EYW » 6:36a ORD
Unknown Company 1 stop (6h16m)
$391
outward: Jul 10, 2019
2:02p ORD » 11:10p EYW
Unknown Company 1 stop (9h08m)
inbound: Jul 13, 2019
9:40p EYW » 6:36a ORD
Unknown Company 1 stop (8h56m)
$395
outward: Feb 22, 2019
12:45a ORD » 2:20a EYW
Unknown Company 1 stop (25h35m)
inbound: Feb 24, 2019
9:40p EYW » 6:59a ORD
Unknown Company 1 stop (33h19m)
$397
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
9:40p EYW » 11:47p ORD
Unknown Company 2 stops (50h07m)
$398
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
3:45p EYW » 11:47p ORD
Unknown Company 2 stops (56h02m)
$398
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
3:45p EYW » 11:47p ORD
Unknown Company 2 stops (56h02m)
$399
outward: Feb 21, 2019
12:15p ORD » 2:20a EYW
Unknown Company 1 stop (38h05m)
inbound: Feb 24, 2019
9:40p EYW » 11:47p ORD
Unknown Company 2 stops (50h07m)
$405
outward: Apr 13, 2019
12:15p ORD » 11:50p EYW
Unknown Company 1 stop (11h35m)
inbound: Apr 21, 2019
12:20a EYW » 3:14p ORD
Unknown Company 2 stops (38h54m)
$413
outward: Apr 13, 2019
12:15p ORD » 6:10p EYW
Unknown Company 1 stop (5h55m)
inbound: Apr 21, 2019
12:20a EYW » 7:01a ORD
Unknown Company 1 stop (6h41m)
$413
outward: Feb 21, 2019
12:15p ORD » 2:20a EYW
Unknown Company 1 stop (14h05m)
inbound: Feb 24, 2019
3:45p EYW » 6:59a ORD
Unknown Company 1 stop (39h14m)
$419
outward: Apr 13, 2019
12:15p ORD » 2:20a EYW
Unknown Company 1 stop (14h05m)
inbound: Apr 21, 2019
12:20a EYW » 3:14p ORD
Unknown Company 2 stops (38h54m)
$421
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
3:45p EYW » 3:04p ORD
Unknown Company 2 stops (23h19m)
$421
outward: Feb 21, 2019
12:15p ORD » 2:20a EYW
Unknown Company 1 stop (38h05m)
inbound: Feb 24, 2019
3:45p EYW » 3:04p ORD
Unknown Company 2 stops (23h19m)
$422
outward: Feb 22, 2019
12:45a ORD » 2:20a EYW
Unknown Company 1 stop (25h35m)
inbound: Feb 24, 2019
9:40p EYW » 4:30p ORD
Unknown Company 1 stop (18h50m)
$455
outward: Apr 13, 2019
11:00p ORD » 9:10p EYW
Unknown Company 2 stops (22h10m)
inbound: Apr 20, 2019
10:45p EYW » 6:19a ORD
Unknown Company 1 stop (31h34m)
$462
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
3:45p EYW » 4:41p ORD
Unknown Company 1 stop (24h56m)
$470
outward: Apr 13, 2019
12:15p ORD » 2:20a EYW
Unknown Company 1 stop (14h05m)
inbound: Apr 21, 2019
12:20a EYW » 6:19a ORD
Unknown Company 2 stops (53h59m)
$480
outward: Feb 22, 2019
12:55a ORD » 2:20a EYW
Unknown Company 1 stop (25h25m)
inbound: Feb 24, 2019
3:45p EYW » 4:41p ORD
Unknown Company 1 stop (24h56m)
$482
outward: Apr 13, 2019
1:59p ORD » 6:10p EYW
Unknown Company 1 stop (28h11m)
inbound: Apr 21, 2019
12:20a EYW » 7:01a ORD
Unknown Company 1 stop (6h41m)
$482
outward: Apr 13, 2019
1:59p ORD » 11:50p EYW
Unknown Company 1 stop (9h51m)
inbound: Apr 21, 2019
12:20a EYW » 7:01a ORD
Unknown Company 1 stop (6h41m)
$485
outward: Apr 13, 2019
1:59p ORD » 6:10p EYW
Unknown Company 1 stop (28h11m)
inbound: Apr 21, 2019
12:20a EYW » 7:01a ORD
Unknown Company 1 stop (6h41m)
$486
outward: Apr 14, 2019
1:40a ORD » 8:15p EYW
Unknown Company 1 stop (18h35m)
inbound: Apr 20, 2019
10:45p EYW » 6:19a ORD
Unknown Company 1 stop (7h34m)
$494
outward: Apr 13, 2019
11:10p MDW » 8:15p EYW
Unknown Company 1 stop (21h05m)
inbound: Apr 20, 2019
8:55p EYW » 5:50a ORD
Unknown Company 1 stop (8h55m)
$494
outward: Apr 13, 2019
11:10p MDW » 8:15p EYW
Unknown Company 1 stop (21h05m)
inbound: Apr 20, 2019
8:55p EYW » 5:50a ORD
Unknown Company 1 stop (8h55m)
$500
outward: Feb 22, 2019
3:45a ORD » 10:45p EYW
American Airlines 1 stop (19h)
inbound: Feb 25, 2019
1:18a EYW » 1:55a ORD
American Airlines 1 stop (24h37m)
$528
outward: Apr 13, 2019
12:15p ORD » 6:10p EYW
Unknown Company 1 stop (5h55m)
inbound: Apr 20, 2019
8:55p EYW » 5:50a ORD
Unknown Company 1 stop (8h55m)
$531
outward: Feb 22, 2019
3:45a ORD » 10:45p EYW
American Airlines 1 stop (19h)
inbound: Feb 25, 2019
1:18a EYW » 2:29a ORD
American Airlines 1 stop (25h11m)
Return
Departure
Find the cheapest Chicago Key West flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Key West with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Key West

Sorry! We haven't found any airline tickets from Chicago to Key West. Try launching another search above.

Travel tips for flights Chicago - Key West

Average flight duration: 25h58m (flight with stopovers)

  • Arrival city:
  • Key West, USA
  • Airport(s):
  • Key West International Airport (EYW)
  • Local time:
  • Jan 18, 2019 2:26 AM, GMT-5
  • Weather:
  • min. 63ºF, max. 75ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jan 18, 2019 1:26 AM, GMT-6
  • Weather:
  • min. 22ºF, max. 28ºF