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
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • any
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • price
  • month of departure
  • month of return
$276
outward: Jan 25, 2019
1:35a ORD » 7:57a SJU
Spirit Airlines 1 stop (6h22m)
inbound: Feb 7, 2019
5:40p SJU » 12:45a ORD
Spirit Airlines 1 stop (7h05m)
$294
outward: Jan 20, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$294
outward: Jan 20, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$294
outward: Jan 20, 2019
6:05p ORD » 7:57a SJU
Spirit Airlines 1 stop (13h52m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 21, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 26, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 21, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 21, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 28, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 22, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 26, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 22, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 23, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 26, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 23, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 27, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$296
outward: Jan 23, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 28, 2019
9:35a SJU » 4:58p ORD
Spirit Airlines 1 stop (7h23m)
$310
outward: Jan 20, 2019
1:35a ORD » 7:50a SJU
Spirit Airlines 1 stop (6h15m)
inbound: Jan 27, 2019
8:59a SJU » 6:12a ORD
Frontier Airlines 1 stop (21h13m)
$310
outward: Jan 20, 2019
1:35a ORD » 7:50a SJU
Spirit Airlines 1 stop (6h15m)
inbound: Jan 27, 2019
8:59a SJU » 6:12a ORD
Frontier Airlines 1 stop (21h13m)
$311
outward: Jan 20, 2019
1:35a ORD » 7:50a SJU
Spirit Airlines 1 stop (6h15m)
inbound: Jan 27, 2019
8:59a SJU » 6:12a ORD
Frontier Airlines 1 stop (21h13m)
$311
outward: Feb 9, 2019
7:11p ORD » 4:02a SJU
American Airlines 1 stop (8h51m)
inbound: Feb 16, 2019
9:02p SJU » 2:35a ORD
American Airlines direct (5h33m)
$311
outward: Feb 9, 2019
7:11p ORD » 4:02a SJU
American Airlines 1 stop (8h51m)
inbound: Feb 16, 2019
9:02p SJU » 2:35a ORD
American Airlines direct (5h33m)
$314
outward: Jan 20, 2019
1:35a ORD » 7:50a SJU
Spirit Airlines 1 stop (6h15m)
inbound: Jan 28, 2019
12:39a SJU » 4:58p ORD
Spirit Airlines 1 stop (16h19m)
$325
outward: Feb 10, 2019
6:05p ORD » 7:59a SJU
Spirit Airlines 1 stop (13h54m)
inbound: Feb 15, 2019
8:11a SJU » 6:38a ORD
JetBlue 1 stop (22h27m)
$329
outward: Jan 16, 2019
1:35a ORD » 7:50a SJU
Spirit Airlines 1 stop (6h15m)
inbound: Jan 22, 2019
12:39a SJU » 9:18p ORD
Spirit Airlines 2 stops (20h39m)
$335
outward: Jan 5, 2019
1:00p ORD » 8:50p SJU
Unknown Company 1 stop (7h50m)
inbound: Jan 13, 2019
8:59a SJU » 6:12a ORD
Frontier Airlines 1 stop (21h13m)
$342
outward: Feb 6, 2019
12:51p ORD » 9:49p SJU
American Airlines 1 stop (8h58m)
inbound: Feb 17, 2019
1:04p SJU » 6:32p ORD
American Airlines direct (5h28m)
$346
outward: Feb 8, 2019
8:36p ORD » 4:29a SJU
American Airlines 1 stop (7h53m)
inbound: Feb 17, 2019
1:04p SJU » 6:32p ORD
American Airlines direct (5h28m)
$353
outward: Apr 27, 2019
6:00a ORD » 10:45a SJU
United Airlines direct (4h45m)
inbound: Apr 29, 2019
9:53p SJU » 10:04p ORD
Unknown Company 1 stop (24h11m)
$357
outward: Mar 30, 2019
4:29a ORD » 9:10a SJU
United Airlines direct (4h41m)
inbound: Apr 7, 2019
11:00a SJU » 1:49p ORD
United Airlines 1 stop (26h49m)
$363
outward: Dec 22, 2018
2:00p ORD » 12:51a SJU
JetBlue 1 stop (10h51m)
inbound: Jan 9, 2019
3:22p SJU » 6:51a ORD
JetBlue 1 stop (15h29m)
$365
outward: Jan 6, 2019
1:35a ORD » 9:15a SJU
Spirit Airlines 1 stop (7h40m)
inbound: Jan 13, 2019
8:39p SJU » 3:08p ORD
Spirit Airlines 1 stop (18h29m)
$370
outward: Jan 5, 2019
1:00p ORD » 8:50p SJU
Unknown Company 1 stop (7h50m)
inbound: Jan 13, 2019
8:59a SJU » 6:12a ORD
Frontier Airlines 1 stop (21h13m)
$371
outward: Mar 2, 2019
11:40p ORD » 4:10p SJU
Spirit Airlines 1 stop (16h30m)
inbound: Mar 9, 2019
9:40p SJU » 5:00a MDW
Southwest Airlines 1 stop (7h20m)
$374
outward: Feb 6, 2019
12:51p ORD » 9:49p SJU
American Airlines 1 stop (8h58m)
inbound: Feb 17, 2019
1:04p SJU » 6:32p ORD
American Airlines direct (5h28m)
Return
Departure
01 January Jan Tuesday $retDate.dayShortName
02 January Jan Wednesday $retDate.dayShortName
03 January Jan Thursday $retDate.dayShortName
04 January Jan Friday $retDate.dayShortName
05 January Jan Saturday $retDate.dayShortName
06 January Jan Sunday $retDate.dayShortName
07 January Jan Monday $retDate.dayShortName
19 December Dec Wednesday $outDate.dayShortName
20 December Dec Thursday $outDate.dayShortName
$747
21 December Dec Friday $outDate.dayShortName
$784 $1,041
22 December Dec Saturday $outDate.dayShortName
$956 $1,034 $854 $916
23 December Dec Sunday $outDate.dayShortName
$777 $750 $933 $770 $820
24 December Dec Monday $outDate.dayShortName
$726 $698 $624 $696 $533
25 December Dec Tuesday $outDate.dayShortName
$710 $759
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
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • all
  • Air Canada
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jan 15, 2019
Spirit Airlines 1 stop
return: Jan 21, 2019
Spirit Airlines 2 stops
JetBlue
outbound: Jan 15, 2019
JetBlue 1 stop
return: Jan 21, 2019
JetBlue 1 stop
United Airlines
outbound: Jan 15, 2019
United Airlines 1 stop
return: Jan 21, 2019
United Airlines 1 stop
Frontier Airlines
outbound: Dec 14, 2018
Frontier Airlines 1 stop
return: Dec 22, 2018
Spirit Airlines 1 stop
Air Canada
outbound: Dec 14, 2018
Air Canada direct
return: Dec 22, 2018
Air Canada 1 stop
American Airlines
outbound: Dec 15, 2018
American Airlines 1 stop
return: Jan 3, 2019
American Airlines 1 stop
Delta Air Lines
outbound: Dec 15, 2018
Delta Air Lines 1 stop
return: Jan 3, 2019
Delta Air Lines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 5h04m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Dec 11, 2018 1:47 PM, GMT-4
  • Weather:
  • min. 71ºF, max. 86ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 11, 2018 11:47 AM, GMT-6
  • Weather:
  • min. 29ºF, max. 35ºF

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!