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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$278
outward: Sep 4, 2018
12:15p ORD » 5:38p EYW
Unknown Company 1 stop (5h23m)
inbound: Sep 7, 2018
11:46p EYW » 7:16a ORD
Unknown Company 1 stop (7h30m)
$327
outward: Dec 7, 2018
2:00p ORD » 9:23p EYW
JetBlue 1 stop (7h23m)
inbound: Dec 11, 2018
11:46p EYW » 6:06a ORD
Unknown Company 1 stop (6h20m)
$328
outward: Dec 8, 2018
1:20a ORD » 12:06a EYW
Unknown Company 1 stop (22h46m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (31h11m)
$328
outward: Dec 7, 2018
12:15p ORD » 12:06a EYW
Unknown Company 1 stop (35h51m)
inbound: Dec 11, 2018
10:48p EYW » 6:59a ORD
Unknown Company 1 stop (32h11m)
$328
outward: Dec 8, 2018
1:20a ORD » 12:06a EYW
Unknown Company 1 stop (22h46m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (31h11m)
$329
outward: Dec 7, 2018
12:15p ORD » 12:06a EYW
Unknown Company 1 stop (35h51m)
inbound: Dec 11, 2018
10:48p EYW » 6:59a ORD
Unknown Company 1 stop (32h11m)
$329
outward: Dec 7, 2018
12:15p ORD » 12:06a EYW
Unknown Company 1 stop (35h51m)
inbound: Dec 11, 2018
10:48p EYW » 6:59a ORD
Unknown Company 1 stop (32h11m)
$329
outward: Dec 7, 2018
12:15p ORD » 12:06a EYW
Unknown Company 1 stop (35h51m)
inbound: Dec 11, 2018
10:48p EYW » 6:59a ORD
Unknown Company 1 stop (32h11m)
$339
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$340
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$342
outward: Dec 7, 2018
2:00p ORD » 9:13p EYW
JetBlue 1 stop (7h13m)
inbound: Dec 11, 2018
6:18p EYW » 6:06a ORD
Unknown Company 1 stop (11h48m)
$343
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 5:01p ORD
Unknown Company 1 stop (17h13m)
$344
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$360
outward: Sep 6, 2018
2:02p ORD » 7:34p EYW
JetBlue 1 stop (5h32m)
inbound: Sep 12, 2018
11:46p EYW » 6:56a ORD
Unknown Company 1 stop (7h10m)
$360
outward: Sep 6, 2018
2:02p ORD » 7:34p EYW
JetBlue 1 stop (5h32m)
inbound: Sep 12, 2018
11:46p EYW » 6:56a ORD
Unknown Company 1 stop (7h10m)
$360
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$361
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$363
outward: Dec 7, 2018
11:50p ORD » 4:52a EYW
American Airlines 1 stop (5h02m)
inbound: Dec 12, 2018
1:05a EYW » 6:57a ORD
American Airlines 1 stop (5h52m)
$363
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
6:18p EYW » 6:59a ORD
Unknown Company 1 stop (12h41m)
$365
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$365
outward: Nov 19, 2018
2:00p ORD » 10:18p EYW
Unknown Company 1 stop (8h18m)
inbound: Dec 5, 2018
6:18p EYW » 6:06a ORD
Unknown Company 1 stop (11h48m)
$365
outward: Aug 2, 2018
8:41p ORD » 4:50a EYW
American Airlines 1 stop (8h09m)
inbound: Aug 7, 2018
1:08a EYW » 4:14p ORD
American Airlines 1 stop (15h06m)
$365
outward: Aug 2, 2018
8:41p ORD » 4:50a EYW
American Airlines 1 stop (8h09m)
inbound: Aug 7, 2018
1:08a EYW » 4:14p ORD
American Airlines 1 stop (15h06m)
$366
outward: Aug 2, 2018
2:00p ORD » 12:37a EYW
American Airlines 1 stop (10h37m)
inbound: Aug 7, 2018
1:08a EYW » 4:14p ORD
American Airlines 1 stop (15h06m)
$366
outward: Aug 2, 2018
11:50p ORD » 4:50a EYW
American Airlines 1 stop (5h)
inbound: Aug 7, 2018
1:08a EYW » 4:14p ORD
American Airlines 1 stop (15h06m)
$366
outward: Aug 2, 2018
8:41p ORD » 4:50a EYW
American Airlines 1 stop (8h09m)
inbound: Aug 7, 2018
1:08a EYW » 4:14p ORD
American Airlines 1 stop (15h06m)
$370
outward: Dec 8, 2018
1:20a ORD » 5:48p EYW
Unknown Company 1 stop (16h28m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$370
outward: Dec 7, 2018
6:25p ORD » 3:32p EYW
Unknown Company 1 stop (21h07m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$370
outward: Dec 7, 2018
2:00p ORD » 5:48p EYW
Unknown Company 1 stop (27h48m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
$371
outward: Dec 7, 2018
12:15p ORD » 5:48p EYW
Unknown Company 1 stop (5h33m)
inbound: Dec 11, 2018
11:48p EYW » 6:59a ORD
Unknown Company 1 stop (7h11m)
Return
Departure
Choose when you'd like to depart to Key West (USA):
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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • all
  • Spirit Airlines
Spirit Airlines
outbound: Sep 4, 2018
Spirit Airlines 1 stop
return: Sep 7, 2018
United Airlines 1 stop

Travel tips for flights Chicago - Key West

Average flight duration: 11h23m (flight with stopovers)

  • Arrival city:
  • Key West, USA
  • Airport(s):
  • Key West International Airport (EYW)
  • Local time:
  • Jul 19, 2018 5:52 AM, GMT-4
  • Weather:
  • min. 76ºF, max. 87ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 19, 2018 4:52 AM, GMT-5
  • Weather:
  • min. 67ºF, max. 76ºF