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

Find cheap airline tickets from Chicago to San Juan by date

  • any
  • 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
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • price
  • month of departure
  • month of return
$301
Spirit Airlines outward: May 7, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)
Spirit Airlines inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$302
Spirit Airlines outward: May 7, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)
Spirit Airlines inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$305
Spirit Airlines outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
Spirit Airlines inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$308
JetBlue outward: Dec 26, 2019
1:55p ORD » 1:50p SJU
JetBlue 1 stop (23h55m)
JetBlue inbound: Jan 6, 2020
2:35p SJU » 7:06a ORD
JetBlue 1 stop (16h31m)
$312
Spirit Airlines outward: May 8, 2019
11:50p ORD » 9:39p SJU
Spirit Airlines 2 stops (21h49m)
Spirit Airlines inbound: May 16, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)
$316
Spirit Airlines outward: May 8, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)
Spirit Airlines inbound: May 15, 2019
5:00p SJU » 6:35a ORD
Spirit Airlines 1 stop (13h35m)
$318
Frontier Airlines outward: Sep 18, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
Spirit Airlines inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)
$326
American Airlines outward: Sep 19, 2019
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)
American Airlines inbound: Sep 26, 2019
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)
$331
Frontier Airlines outward: Sep 9, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
Frontier Airlines inbound: Sep 13, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$333
Frontier Airlines outward: Sep 19, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)
Frontier Airlines inbound: Sep 26, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$335
Spirit Airlines outward: May 7, 2019
4:42p ORD » 3:13a SJU
Spirit Airlines 2 stops (10h31m)
Spirit Airlines inbound: May 22, 2019
5:00p SJU » 6:35a ORD
Spirit Airlines 1 stop (13h35m)
$337
Spirit Airlines outward: May 7, 2019
4:42p ORD » 3:13a SJU
Spirit Airlines 2 stops (10h31m)
Spirit Airlines inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$343
JetBlue outward: Sep 18, 2019
9:09p ORD » 8:11a SJU
JetBlue 1 stop (11h02m)
Spirit Airlines inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)
$343
JetBlue outward: Sep 18, 2019
9:09p ORD » 8:11a SJU
JetBlue 1 stop (11h02m)
Spirit Airlines inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)
$343
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)
$344
Spirit Airlines outward: May 9, 2019
11:50p ORD » 8:38a SJU
Spirit Airlines 2 stops (8h48m)
Spirit Airlines inbound: May 10, 2019
5:00p SJU » 7:27a ORD
Spirit Airlines 1 stop (14h27m)
$344
Spirit Airlines outward: Apr 24, 2019
11:40p ORD » 8:45a SJU
Spirit Airlines 2 stops (33h05m)
Spirit Airlines inbound: Apr 30, 2019
1:53a SJU » 6:19a ORD
Spirit Airlines 1 stop (28h26m)
$347
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)
$347
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)
$348
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)
$349
Spirit Airlines outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
Spirit Airlines inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$352
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$353
Spirit Airlines outward: May 9, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
Spirit Airlines inbound: May 10, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$353
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$354
Spirit Airlines outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
Spirit Airlines inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)
$355
JetBlue outward: May 8, 2019
1:57p ORD » 8:30a SJU
JetBlue 1 stop (18h33m)
JetBlue inbound: May 16, 2019
2:32a SJU » 5:48a ORD
JetBlue 1 stop (27h16m)
$356
American Airlines outward: Sep 30, 2019
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)
American Airlines inbound: Oct 7, 2019
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)
$358
Unknown Company outward: May 8, 2019
11:50p ORD » 8:21p SJU
Unknown Company 1 stop (20h31m)
Unknown Company inbound: May 15, 2019
9:50a SJU » 3:15a ORD
Unknown Company 1 stop (17h25m)
$360
Spirit Airlines outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
Spirit Airlines inbound: May 23, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)
$360
Spirit Airlines outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
Spirit Airlines inbound: May 23, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)
Return
Departure
01 January Jan Wednesday $retDate.dayShortName
02 January Jan Thursday $retDate.dayShortName
03 January Jan Friday $retDate.dayShortName
04 January Jan Saturday $retDate.dayShortName
05 January Jan Sunday $retDate.dayShortName
06 January Jan Monday $retDate.dayShortName
07 January Jan Tuesday $retDate.dayShortName
21 December Dec Saturday $outDate.dayShortName
22 December Dec Sunday $outDate.dayShortName
23 December Dec Monday $outDate.dayShortName
$656 $694 $798
24 December Dec Tuesday $outDate.dayShortName
$694 $755
25 December Dec Wednesday $outDate.dayShortName
26 December Dec Thursday $outDate.dayShortName
$299 $813
27 December Dec Friday $outDate.dayShortName
$745
Find the cheapest Chicago San Juan flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - San Juan with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to San Juan

  • any
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • all
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Apr 26, 2019
Spirit Airlines 1 stop
return: Apr 29, 2019
Spirit Airlines 2 stops
JetBlue
outbound: Dec 18, 2019
JetBlue 1 stop
return: Jan 2, 2020
JetBlue 1 stop
Frontier Airlines
outbound: Apr 26, 2019
Frontier Airlines 1 stop
return: Apr 29, 2019
Spirit Airlines 1 stop
American Airlines
outbound: Apr 26, 2019
American Airlines direct
return: Apr 29, 2019
American Airlines 1 stop
United Airlines
outbound: Apr 26, 2019
United Airlines direct
return: Apr 29, 2019
United Airlines 1 stop
Delta Air Lines
outbound: Apr 24, 2019
Delta Air Lines 1 stop
return: Apr 29, 2019
Delta Air Lines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 4h58m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Apr 20, 2019 8:20 AM, GMT-4
  • Weather:
  • min. 61ºF, max. 72ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Apr 20, 2019 7:20 AM, GMT-5
  • Weather:
  • min. 44ºF, max. 60ºF

Why travel by plane from Chicago to San Juan?

When traveling from Chicago to San Juan, travelers are able to take advantage of daily non-stop flights between the two cities, operated by a number of airlines including regular and low-cost operators. These include American Airlines, Southwest Airlines and United Airlines, which operate direct flights to San Juan with a flight time of around 4h 40m. Connecting flights are also available with a flight time of upwards of 6h. Departing from either O'Hare International Airport or Chicago Midway International Airport, flights touch down in San Juan's Luis Muñoz Marín International Airport.

What is there to see and do in San Juan?

The Puerto Rican capital city of San Juan is home to a host of activities and sights for visitors to enjoy. As well as the must-visit area of Old San Juan, filled with colorful houses and interesting attractions, there's also the opportunity to learn more about Bacardi rum at the Casa Bacardi factory and museum. Other museums to visit include the Museo de las Americas, the Museum of the Sea, and the Museum of Art Puerto Rico. After a day of exploring, relax in one of San Juan's restaurants or bars – the city boasts a lively nightlife scene!