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
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • price
  • month of departure
  • month of return
$240
Spirit Airlines outward: Jan 29, 2020
2:00p ORD » 6:20a SJU
Spirit Airlines 1 stop (16h20m)
Spirit Airlines inbound: Feb 8, 2020
11:30a SJU » 4:39a ORD
Spirit Airlines 1 stop (17h09m)
$251
Spirit Airlines outward: Jan 29, 2020
2:00p ORD » 6:20a SJU
Spirit Airlines 1 stop (16h20m)
Spirit Airlines inbound: Feb 8, 2020
10:28p SJU » 7:05a ORD
Spirit Airlines 1 stop (8h37m)
$279
Spirit Airlines outward: Dec 5, 2019
11:24p ORD » 3:40p SJU
Spirit Airlines 1 stop (16h16m)
Spirit Airlines inbound: Dec 13, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 1 stop (19h24m)
$285
Spirit Airlines outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)
Spirit Airlines inbound: Feb 8, 2020
3:20p SJU » 4:39a ORD
Spirit Airlines 1 stop (13h19m)
$286
Spirit Airlines outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)
Spirit Airlines inbound: Feb 9, 2020
4:59a SJU » 5:00p ORD
Spirit Airlines 1 stop (12h01m)
$290
Spirit Airlines outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)
Unknown Company inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)
$291
Spirit Airlines outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)
Unknown Company inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)
$292
Spirit Airlines outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)
Unknown Company inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)
$298
Spirit Airlines outward: Dec 10, 2019
1:20a ORD » 4:31p SJU
Spirit Airlines 1 stop (15h11m)
Spirit Airlines inbound: Dec 17, 2019
8:03p SJU » 5:15a ORD
Spirit Airlines 1 stop (9h12m)
$302
Spirit Airlines outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)
Spirit Airlines inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)
$312
Spirit Airlines outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)
Spirit Airlines inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)
$312
Spirit Airlines outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)
Spirit Airlines inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)
$325
Spirit Airlines outward: Dec 6, 2019
11:24p ORD » 3:40p SJU
Spirit Airlines 1 stop (16h16m)
United Airlines inbound: Dec 19, 2019
8:35p SJU » 1:46a ORD
United Airlines direct (5h11m)
$341
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
United Airlines inbound: Mar 8, 2020
11:05a SJU » 4:12p ORD
United Airlines direct (5h07m)
$341
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
United Airlines inbound: Mar 8, 2020
11:05a SJU » 4:12p ORD
United Airlines direct (5h07m)
$342
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
United Airlines inbound: Mar 8, 2020
6:45a SJU » 11:46a ORD
United Airlines direct (5h01m)
$376
American Airlines outward: Apr 25, 2020
10:30p ORD » 3:25a SJU
American Airlines direct (4h55m)
American Airlines inbound: Apr 29, 2020
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)
$379
American Airlines outward: Apr 25, 2020
10:30p ORD » 3:25a SJU
American Airlines direct (4h55m)
American Airlines inbound: Apr 29, 2020
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)
$409
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
United Airlines inbound: Mar 8, 2020
7:01a SJU » 4:30p ORD
United Airlines 1 stop (9h29m)
$410
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
United Airlines inbound: Mar 8, 2020
7:01a SJU » 4:30p ORD
United Airlines 1 stop (9h29m)
$415
Frontier Airlines outward: Dec 2, 2019
5:29p ORD » 7:59a SJU
Frontier Airlines 1 stop (14h30m)
Frontier Airlines inbound: Dec 17, 2019
8:55a SJU » 3:03a ORD
Frontier Airlines 1 stop (18h08m)
$415
Frontier Airlines outward: Dec 2, 2019
5:29p ORD » 7:59a SJU
Frontier Airlines 1 stop (14h30m)
Frontier Airlines inbound: Dec 17, 2019
8:55a SJU » 3:03a ORD
Frontier Airlines 1 stop (18h08m)
$436
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
JetBlue inbound: Mar 9, 2020
1:05a SJU » 6:49a ORD
JetBlue 1 stop (29h44m)
$436
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)
JetBlue inbound: Mar 9, 2020
1:05a SJU » 6:49a ORD
JetBlue 1 stop (29h44m)
$453
Frontier Airlines outward: Mar 5, 2020
2:50p ORD » 7:55a SJU
Frontier Airlines 1 stop (17h05m)
Frontier Airlines inbound: Mar 8, 2020
7:55a SJU » 2:03a ORD
Frontier Airlines 1 stop (18h08m)
$466
JetBlue outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)
JetBlue inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)
$466
JetBlue outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)
JetBlue inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)
$466
JetBlue outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)
JetBlue inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)
$479
Spirit Airlines outward: Nov 24, 2019
3:45a ORD » 6:57p SJU
Spirit Airlines 1 stop (15h12m)
Spirit Airlines inbound: Dec 2, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)
$494
Frontier Airlines outward: Dec 26, 2019
2:50p ORD » 9:58p SJU
Frontier Airlines direct (7h08m)
Spirit Airlines inbound: Jan 10, 2020
4:59a SJU » 5:00p ORD
Spirit Airlines 1 stop (12h01m)
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
18 December Dec Wednesday $outDate.dayShortName
$566 $662 $511
19 December Dec Thursday $outDate.dayShortName
$558 $558 $549
20 December Dec Friday $outDate.dayShortName
$620
21 December Dec Saturday $outDate.dayShortName
$610
22 December Dec Sunday $outDate.dayShortName
$720
23 December Dec Monday $outDate.dayShortName
$591 $625 $447 $614 $560
24 December Dec Tuesday $outDate.dayShortName
$581 $801 $727 $568
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
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • all
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
JetBlue
outbound: Dec 18, 2019
JetBlue 1 stop
return: Dec 23, 2019
Spirit Airlines 1 stop
Spirit Airlines
outbound: Nov 22, 2019
Spirit Airlines 1 stop
return: Dec 1, 2019
Spirit Airlines 2 stops
Frontier Airlines
outbound: Nov 22, 2019
Frontier Airlines 1 stop
return: Dec 1, 2019
Air Canada 1 stop
United Airlines
outbound: Nov 22, 2019
United Airlines 1 stop
return: Dec 1, 2019
United Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 7h13m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Oct 23, 2019 9:42 PM, GMT-4
  • Weather:
  • min. 59ºF, max. 83ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 23, 2019 8:42 PM, GMT-5
  • Weather:
  • min. 42ºF, max. 50ºF

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!