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
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • any
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • price
  • month of departure
  • month of return
$242
Spirit Airlines outward: Sep 18, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)
Spirit Airlines inbound: Sep 23, 2019
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
$243
Spirit Airlines outward: Oct 3, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)
Spirit Airlines inbound: Oct 31, 2019
11:20a SJU » 2:05a ORD
Spirit Airlines 1 stop (14h45m)
$247
Spirit Airlines outward: Sep 18, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)
Spirit Airlines inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)
$252
Spirit Airlines outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)
Spirit Airlines inbound: Nov 16, 2019
9:30a SJU » 5:44p ORD
Spirit Airlines 1 stop (8h14m)
$253
Spirit Airlines outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)
Spirit Airlines inbound: Nov 16, 2019
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
$258
Spirit Airlines outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)
Spirit Airlines inbound: Nov 16, 2019
9:30a SJU » 5:01p ORD
Spirit Airlines 1 stop (7h31m)
$259
Spirit Airlines outward: Sep 18, 2019
10:40p ORD » 5:59a SJU
Spirit Airlines 1 stop (7h19m)
Spirit Airlines inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)
$259
Frontier Airlines outward: Sep 24, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)
Spirit Airlines inbound: Oct 1, 2019
8:20a SJU » 5:37p ORD
Spirit Airlines 1 stop (9h17m)
$261
Spirit Airlines outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)
Spirit Airlines inbound: Nov 16, 2019
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
$261
Spirit Airlines outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)
Spirit Airlines inbound: Nov 16, 2019
5:21p SJU » 6:59a ORD
Spirit Airlines 1 stop (13h38m)
$263
Spirit Airlines outward: Sep 28, 2019
11:50p ORD » 3:53p SJU
Spirit Airlines 1 stop (16h03m)
Spirit Airlines inbound: Oct 7, 2019
2:55a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h30m)
$263
Spirit Airlines outward: Jan 29, 2020
12:15p ORD » 4:08a SJU
Spirit Airlines 1 stop (15h53m)
Spirit Airlines inbound: Feb 9, 2020
4:59a SJU » 5:00p ORD
Spirit Airlines 1 stop (12h01m)
$264
Spirit Airlines outward: Sep 18, 2019
10:40p ORD » 5:59a SJU
Spirit Airlines 1 stop (7h19m)
Spirit Airlines inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)
$264
Spirit Airlines outward: Sep 28, 2019
11:50p ORD » 3:53p SJU
Spirit Airlines 1 stop (16h03m)
Spirit Airlines inbound: Oct 7, 2019
2:55a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h30m)
$267
Frontier Airlines outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)
Unknown Company inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)
$267
Frontier Airlines outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)
Unknown Company inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)
$267
Frontier Airlines outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)
Unknown Company inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)
$270
Spirit Airlines outward: Sep 28, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)
Spirit Airlines inbound: Oct 7, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)
$274
Spirit Airlines outward: Sep 28, 2019
4:30p ORD » 3:05a SJU
Spirit Airlines 1 stop (10h35m)
Spirit Airlines inbound: Oct 7, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)
$276
Spirit Airlines outward: Sep 18, 2019
4:30p ORD » 9:37p SJU
Spirit Airlines 1 stop (29h07m)
Spirit Airlines inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)
$281
Frontier Airlines outward: Aug 21, 2019
2:49p ORD » 7:07a SJU
Frontier Airlines 1 stop (16h18m)
Frontier Airlines inbound: Aug 28, 2019
9:35a SJU » 9:48p ORD
Frontier Airlines 1 stop (12h13m)
$282
Spirit Airlines outward: Oct 3, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)
Spirit Airlines inbound: Oct 31, 2019
7:22p SJU » 1:49a ORD
Spirit Airlines 1 stop (6h27m)
$291
Spirit Airlines outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)
Spirit Airlines inbound: Nov 16, 2019
5:21p SJU » 6:59a ORD
Spirit Airlines 1 stop (13h38m)
$294
Frontier Airlines outward: Jan 30, 2020
12:23a ORD » 7:19a SJU
Frontier Airlines 1 stop (6h56m)
Frontier Airlines inbound: Feb 8, 2020
8:56a SJU » 4:08p ORD
Frontier Airlines 1 stop (7h12m)
$294
Frontier Airlines outward: Jan 29, 2020
2:00p ORD » 8:57p SJU
Frontier Airlines 1 stop (6h57m)
Frontier Airlines inbound: Feb 8, 2020
8:56a SJU » 4:08p ORD
Frontier Airlines 1 stop (7h12m)
$304
Spirit Airlines outward: Oct 3, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)
Spirit Airlines inbound: Oct 31, 2019
11:20a SJU » 2:05a ORD
Spirit Airlines 1 stop (14h45m)
$307
Spirit Airlines outward: Aug 30, 2019
11:08p ORD » 6:26p SJU
Spirit Airlines 1 stop (19h18m)
Spirit Airlines inbound: Sep 9, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)
$318
Spirit Airlines outward: Nov 13, 2019
4:24p ORD » 9:28p SJU
Spirit Airlines 1 stop (29h04m)
Spirit Airlines inbound: Nov 17, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)
$318
Unknown Company outward: Aug 31, 2019
4:40a ORD » 9:31p SJU
Unknown Company 1 stop (16h51m)
Spirit Airlines inbound: Sep 9, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)
$320
Spirit Airlines outward: Nov 13, 2019
4:27p ORD » 9:28p SJU
Spirit Airlines 1 stop (29h01m)
Spirit Airlines inbound: Nov 16, 2019
8:03p SJU » 2:58p ORD
Spirit Airlines 1 stop (18h55m)
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
20 December Dec Friday $outDate.dayShortName
$771
21 December Dec Saturday $outDate.dayShortName
22 December Dec Sunday $outDate.dayShortName
$800
23 December Dec Monday $outDate.dayShortName
$391 $600 $598 $662
24 December Dec Tuesday $outDate.dayShortName
25 December Dec Wednesday $outDate.dayShortName
$623
26 December Dec Thursday $outDate.dayShortName
$721 $862 $764
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
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • all
  • Air New Zealand
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 23, 2019
Spirit Airlines 1 stop
return: Aug 26, 2019
Spirit Airlines 1 stop
Southwest Airlines
outbound: Nov 4, 2019
Southwest Airlines 1 stop
return: Dec 2, 2019
Spirit Airlines 1 stop
JetBlue
outbound: Dec 17, 2019
JetBlue 1 stop
return: Jan 7, 2020
JetBlue 1 stop
Frontier Airlines
outbound: Aug 23, 2019
Frontier Airlines 1 stop
return: Aug 26, 2019
Spirit Airlines 1 stop
United Airlines
outbound: Aug 23, 2019
United Airlines direct
return: Aug 26, 2019
United Airlines 1 stop
Air New Zealand
outbound: Dec 26, 2019
Air New Zealand direct
return: Dec 29, 2019
Air Canada 1 stop
American Airlines
outbound: Dec 18, 2019
American Airlines 1 stop
return: Jan 7, 2020
Frontier Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 5h22m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Aug 20, 2019 11:59 AM, GMT-4
  • Weather:
  • min. 39ºF, max. 65ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Aug 20, 2019 10:59 AM, GMT-5
  • Weather:
  • min. 74ºF, max. 85ºF

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!