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
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$262
outward: Dec 7, 2018
12:15p ORD » 9:23p EYW
Unknown Company 1 stop (33h08m)
inbound: Dec 11, 2018
3:05p EYW » 6:59a ORD
Unknown Company 1 stop (15h54m)
$275
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (7h13m)
$276
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (7h13m)
$277
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (7h13m)
$277
outward: Jan 23, 2019
1:55p ORD » 9:23p EYW
Unknown Company 1 stop (7h28m)
inbound: Jan 24, 2019
11:46p EYW » 6:38a ORD
Unknown Company 1 stop (6h52m)
$277
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (39h49m)
$277
outward: Dec 8, 2018
1:23a ORD » 10:05p EYW
Unknown Company 1 stop (20h42m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$277
outward: Dec 8, 2018
1:23a ORD » 10:05p EYW
Unknown Company 1 stop (20h42m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$277
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$278
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (7h13m)
$279
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (7h13m)
$279
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$279
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$279
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (15h49m)
$280
outward: Dec 8, 2018
1:23a ORD » 7:34p EYW
Unknown Company 1 stop (18h11m)
inbound: Dec 11, 2018
8:56p EYW » 5:45a ORD
Unknown Company 1 stop (8h49m)
$282
outward: Dec 8, 2018
1:23a ORD » 10:53p EYW
Unknown Company 1 stop (21h30m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (31h13m)
$282
outward: Dec 8, 2018
1:23a ORD » 10:53p EYW
Unknown Company 1 stop (21h30m)
inbound: Dec 11, 2018
11:46p EYW » 6:59a ORD
Unknown Company 1 stop (31h13m)
$283
outward: Dec 7, 2018
1:00p ORD » 3:25p EYW
Unknown Company 1 stop (26h25m)
inbound: Dec 11, 2018
3:55p EYW » 3:22a ORD
Unknown Company 1 stop (11h27m)
$284
outward: Dec 8, 2018
1:23a ORD » 2:30a EYW
Unknown Company 1 stop (25h07m)
inbound: Dec 11, 2018
3:10p EYW » 6:59a ORD
Unknown Company 1 stop (39h49m)
$290
outward: Dec 8, 2018
1:23a ORD » 7:34p EYW
Unknown Company 1 stop (18h11m)
inbound: Dec 11, 2018
3:55p EYW » 4:55a ORD
Unknown Company 1 stop (13h)
$290
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
3:55p EYW » 9:19p ORD
Unknown Company 1 stop (5h24m)
$290
outward: Dec 7, 2018
12:15p ORD » 2:31a EYW
Unknown Company 1 stop (14h16m)
inbound: Dec 11, 2018
3:55p EYW » 4:55a ORD
Unknown Company 1 stop (13h)
$291
outward: Dec 7, 2018
12:15p ORD » 2:31a EYW
Unknown Company 1 stop (14h16m)
inbound: Dec 11, 2018
3:55p EYW » 4:55a ORD
Unknown Company 1 stop (13h)
$291
outward: Dec 7, 2018
12:15p ORD » 2:31a EYW
Unknown Company 1 stop (14h16m)
inbound: Dec 11, 2018
3:55p EYW » 4:55a ORD
Unknown Company 1 stop (13h)
$291
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
8:56p EYW » 5:45a ORD
Unknown Company 1 stop (8h49m)
$291
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
3:55p EYW » 9:19p ORD
Unknown Company 1 stop (5h24m)
$291
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
8:56p EYW » 5:45a ORD
Unknown Company 1 stop (8h49m)
$292
outward: Dec 7, 2018
12:15p ORD » 2:31a EYW
Unknown Company 1 stop (14h16m)
inbound: Dec 11, 2018
3:55p EYW » 4:55a ORD
Unknown Company 1 stop (13h)
$294
outward: Dec 8, 2018
1:20a ORD » 7:34p EYW
Unknown Company 1 stop (18h14m)
inbound: Dec 11, 2018
8:56p EYW » 5:45a ORD
Unknown Company 1 stop (8h49m)
$318
outward: Feb 21, 2019
2:00p ORD » 5:48p EYW
Unknown Company 1 stop (27h48m)
inbound: Feb 24, 2019
6:18p EYW » 6:38a ORD
Unknown Company 1 stop (12h20m)
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: Las Vegas - Key West New York - Key West London - Key West Miami - Key West See more routes

Airlines operating flights from Chicago to Key West

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • all
  • American Airlines
  • JetBlue
  • Spirit Airlines
Spirit Airlines
outbound: Oct 4, 2018
Spirit Airlines 1 stop
return: Oct 8, 2018
United Airlines 1 stop
JetBlue
outbound: Oct 4, 2018
JetBlue 1 stop
return: Oct 8, 2018
JetBlue 2 stops
American Airlines
outbound: Oct 4, 2018
American Airlines 1 stop
return: Oct 8, 2018
American Airlines 1 stop

Travel tips for flights Chicago - Key West

Average flight duration: 19h11m (flight with stopovers)

  • Arrival city:
  • Key West, USA
  • Airport(s):
  • Key West International Airport (EYW)
  • Local time:
  • Sep 23, 2018 12:17 AM, GMT-4
  • Weather:
  • min. 83ºF, max. 86ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 22, 2018 11:17 PM, GMT-5
  • Weather:
  • min. 61ºF, max. 71ºF