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
  • 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
$299
Frontier Airlines outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)
Frontier Airlines inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)
$302
Frontier Airlines outward: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)
Frontier Airlines inbound: Aug 27, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$303
Frontier Airlines outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)
Frontier Airlines inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)
$304
Frontier Airlines outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)
Frontier Airlines inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)
$304
Frontier Airlines outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)
Frontier Airlines inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)
$304
Frontier Airlines outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)
Frontier Airlines inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)
$310
JetBlue outward: Aug 21, 2019
2:02p ORD » 10:42p SJU
JetBlue 1 stop (8h40m)
Frontier Airlines inbound: Aug 28, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$323
JetBlue outward: Jul 5, 2019
2:02p ORD » 8:44p SJU
JetBlue direct (6h42m)
JetBlue inbound: Jul 6, 2019
8:26a SJU » 4:34p ORD
JetBlue 1 stop (8h08m)
$328
JetBlue outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)
JetBlue inbound: Feb 8, 2020
3:55p SJU » 1:00a ORD
JetBlue 1 stop (9h05m)
$328
JetBlue outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)
JetBlue inbound: Feb 8, 2020
10:00p SJU » 6:42a ORD
JetBlue 1 stop (8h42m)
$328
JetBlue outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)
JetBlue inbound: Feb 8, 2020
3:55p SJU » 1:00a ORD
JetBlue 1 stop (9h05m)
$333
JetBlue outward: Dec 27, 2019
1:55p ORD » 1:50p SJU
JetBlue 1 stop (23h55m)
JetBlue inbound: Jan 6, 2020
6:43a SJU » 3:41p ORD
JetBlue 1 stop (8h58m)
$339
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$339
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$339
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$339
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$340
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$341
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$341
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$341
JetBlue outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)
JetBlue inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)
$348
JetBlue outward: Sep 18, 2019
5:17p ORD » 9:22a SJU
JetBlue 1 stop (16h05m)
JetBlue inbound: Sep 23, 2019
5:10p SJU » 6:39a ORD
JetBlue 1 stop (13h29m)
$349
American Airlines outward: Jan 29, 2020
12:45p ORD » 7:23p SJU
American Airlines 1 stop (6h38m)
American Airlines inbound: Feb 8, 2020
10:40p SJU » 6:28a ORD
American Airlines 1 stop (7h48m)
$351
Spirit Airlines outward: Jul 23, 2019
4:40p ORD » 3:10a SJU
Spirit Airlines 1 stop (10h30m)
Frontier Airlines inbound: Aug 20, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$351
Frontier Airlines outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)
Spirit Airlines inbound: Nov 19, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)
$351
Frontier Airlines outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)
Spirit Airlines inbound: Nov 20, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)
$351
United Airlines outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)
Frontier Airlines inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$351
United Airlines outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)
Frontier Airlines inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$351
United Airlines outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)
Frontier Airlines inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$351
United Airlines outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)
Frontier Airlines inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
$352
United Airlines outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)
Frontier Airlines inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)
Return
Departure
30 June Jun Sunday $retDate.dayShortName
01 July Jul Monday $retDate.dayShortName
02 July Jul Tuesday $retDate.dayShortName
03 July Jul Wednesday $retDate.dayShortName
04 July Jul Thursday $retDate.dayShortName
05 July Jul Friday $retDate.dayShortName
06 July Jul Saturday $retDate.dayShortName
18 June Jun Tuesday $outDate.dayShortName
$394 $416 $480
19 June Jun Wednesday $outDate.dayShortName
$425 $462
20 June Jun Thursday $outDate.dayShortName
$523 $526 $454
21 June Jun Friday $outDate.dayShortName
$514 $541 $443
22 June Jun Saturday $outDate.dayShortName
$454
23 June Jun Sunday $outDate.dayShortName
24 June Jun Monday $outDate.dayShortName
$452
Choose when you'd like to depart to San Juan (Puerto Rico):
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
  • 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
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
JetBlue
outbound: Sep 6, 2019
JetBlue 1 stop
return: Sep 23, 2019
JetBlue 1 stop
Spirit Airlines
outbound: Sep 6, 2019
Spirit Airlines 1 stop
return: Sep 23, 2019
Spirit Airlines 1 stop
Southwest Airlines
outbound: Jun 21, 2019
Southwest Airlines 1 stop
return: Jul 15, 2019
Spirit Airlines 1 stop
Frontier Airlines
outbound: Jul 23, 2019
Frontier Airlines 1 stop
return: Jul 30, 2019
Frontier Airlines 1 stop
American Airlines
outbound: Nov 2, 2019
American Airlines 1 stop
return: Nov 10, 2019
Frontier Airlines 1 stop
United Airlines
outbound: Jul 26, 2019
United Airlines 1 stop
return: Aug 5, 2019
United Airlines 1 stop
Delta Air Lines
outbound: Sep 6, 2019
Delta Air Lines 1 stop
return: Sep 23, 2019
Spirit Airlines 1 stop
Air Canada
outbound: Dec 21, 2019
Air Canada 1 stop
return: Dec 29, 2019
Delta Air Lines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 4h59m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Jun 17, 2019 4:41 AM, GMT-4
  • Weather:
  • min. 35ºF, max. 54ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 17, 2019 3:41 AM, GMT-5
  • Weather:
  • min. 54ºF, max. 63ºF

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!