Take off on cheap flights from San Juan to Chicago, your adventure starts now!

Find cheap airline tickets from San Juan to Chicago by date

  • any
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • any
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • price
  • month of departure
  • month of return
$372
Delta Air Lines outward: Aug 22, 2019
10:27p SJU » 6:26a MDW
Delta Air Lines 1 stop (7h59m)
United Airlines inbound: Sep 2, 2019
4:30a ORD » 6:00p SJU
United Airlines 1 stop (13h30m)
$376
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$377
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$378
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$379
Unknown Company outward: Aug 20, 2019
2:30p SJU » 1:21a ORD
Unknown Company 1 stop (10h51m)
Unknown Company inbound: Sep 1, 2019
12:00a ORD » 8:17p SJU
Unknown Company 1 stop (20h17m)
$379
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$380
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$380
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$380
Spirit Airlines outward: Aug 1, 2019
7:26p SJU » 3:13a ORD
Spirit Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$382
Spirit Airlines outward: Jul 10, 2019
2:45a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h40m)
Spirit Airlines inbound: Jul 30, 2019
4:40p ORD » 3:18a SJU
Spirit Airlines 1 stop (10h38m)
$385
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$385
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$385
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$386
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$387
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$387
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$387
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$387
Frontier Airlines outward: Aug 6, 2019
9:40a SJU » 3:13a ORD
Frontier Airlines 1 stop (17h33m)
Frontier Airlines inbound: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
$387
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$388
Frontier Airlines outward: Oct 11, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 14, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$388
Spirit Airlines outward: Jul 10, 2019
2:45a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h40m)
Spirit Airlines inbound: Jul 30, 2019
4:40p ORD » 3:18a SJU
Spirit Airlines 1 stop (10h38m)
$389
Frontier Airlines outward: Sep 26, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Frontier Airlines inbound: Oct 9, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
$390
JetBlue outward: Aug 23, 2019
3:20a SJU » 6:49a ORD
JetBlue 1 stop (27h29m)
JetBlue inbound: Sep 5, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
$392
Spirit Airlines outward: Jul 9, 2019
7:26p SJU » 3:18a ORD
Spirit Airlines 1 stop (7h52m)
Spirit Airlines inbound: Jul 30, 2019
6:50p ORD » 3:40p SJU
Spirit Airlines 1 stop (20h50m)
$392
Spirit Airlines outward: Jul 10, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)
Spirit Airlines inbound: Jul 30, 2019
4:40p ORD » 3:18a SJU
Spirit Airlines 1 stop (10h38m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest San Juan Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for San Juan - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from San Juan to Chicago

  • any
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • all
  • Air Canada
  • Air New Zealand
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • SAS
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 30, 2019
Spirit Airlines 1 stop
return: Aug 20, 2019
Spirit Airlines 1 stop
JetBlue
outbound: Aug 1, 2019
JetBlue 1 stop
return: Aug 20, 2019
JetBlue 1 stop
Southwest Airlines
outbound: Sep 26, 2019
Southwest Airlines 1 stop
return: Oct 9, 2019
United Airlines 1 stop
Frontier Airlines
outbound: Jul 16, 2019
Frontier Airlines 1 stop
return: Aug 20, 2019
Frontier Airlines 1 stop
United Airlines
outbound: Aug 1, 2019
United Airlines 1 stop
return: Aug 20, 2019
Frontier Airlines 1 stop
Air Canada
outbound: Jul 16, 2019
Air Canada 1 stop
return: Aug 20, 2019
United Airlines 1 stop
SAS
outbound: Aug 1, 2019
SAS 1 stop
return: Aug 20, 2019
United Airlines 1 stop
American Airlines
outbound: Jul 30, 2019
American Airlines direct
return: Aug 20, 2019
American Airlines direct
Air New Zealand
outbound: Jan 29, 2020
Air New Zealand direct
return: Feb 8, 2020
Aer Lingus 2 stops

Travel tips for flights San Juan - Chicago

Average flight duration: 13h (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 17, 2019 9:43 PM, GMT-5
  • Weather:
  • min. 55ºF, max. 67ºF
  • Departure city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Jun 17, 2019 10:43 PM, GMT-4
  • Weather:
  • min. 39ºF, max. 63ºF