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
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • any
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • price
  • month of departure
  • month of return
$240
outward: Jan 24, 2018
1:25a ORD » 2:26p SJU
Unknown Company 1 stop (13h01m)
inbound: Jan 30, 2018
10:44p SJU » 6:58a ORD
Spirit Airlines 1 stop (8h14m)
$245
outward: Jan 31, 2018
10:05p ORD » 8:30p SJU
Unknown Company 1 stop (22h25m)
inbound: Feb 7, 2018
10:44p SJU » 6:58a ORD
Spirit Airlines 1 stop (8h14m)
$259
outward: Feb 11, 2018
1:25a ORD » 7:12p SJU
Spirit Airlines 1 stop (17h47m)
inbound: Feb 28, 2018
10:28p SJU » 7:01a ORD
Unknown Company 1 stop (8h33m)
$259
outward: Feb 11, 2018
1:25a ORD » 7:12p SJU
Spirit Airlines 1 stop (17h47m)
inbound: Feb 28, 2018
10:28p SJU » 7:01a ORD
Unknown Company 1 stop (8h33m)
$263
outward: Jan 23, 2018
1:25a ORD » 2:26p SJU
Unknown Company 1 stop (13h01m)
inbound: Jan 25, 2018
10:44p SJU » 6:58a ORD
Spirit Airlines 1 stop (8h14m)
$307
outward: Jan 21, 2018
11:25p ORD » 7:12p SJU
Spirit Airlines 2 stops (19h47m)
inbound: Jan 25, 2018
10:44p SJU » 5:55a ORD
Spirit Airlines 2 stops (31h11m)
$323
outward: Mar 7, 2018
6:15p ORD » 4:57a SJU
Unknown Company 1 stop (10h42m)
inbound: Mar 15, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$342
outward: Jan 22, 2018
2:00p ORD » 2:26p SJU
JetBlue 1 stop (24h26m)
inbound: Jan 26, 2018
2:14a SJU » 6:01a ORD
JetBlue 1 stop (27h47m)
$344
outward: Jan 22, 2018
1:25a ORD » 2:26p SJU
Unknown Company 1 stop (13h01m)
inbound: Jan 25, 2018
10:44p SJU » 6:58a ORD
Spirit Airlines 1 stop (8h14m)
$369
outward: Jan 21, 2018
2:00p ORD » 4:28p SJU
JetBlue 1 stop (26h28m)
inbound: Jan 25, 2018
4:10p SJU » 6:01a ORD
JetBlue 1 stop (13h51m)
$371
outward: Mar 16, 2018
1:19p ORD » 8:34p SJU
American Airlines 1 stop (7h15m)
inbound: Mar 24, 2018
9:25p SJU » 6:57a ORD
American Airlines 1 stop (8h32m)
$380
outward: Mar 10, 2018
12:50a ORD » 7:49a SJU
United Airlines 1 stop (6h59m)
inbound: Mar 18, 2018
7:45a SJU » 4:46p ORD
United Airlines 1 stop (9h01m)
$383
outward: Mar 10, 2018
12:50a ORD » 7:49a SJU
United Airlines 1 stop (6h59m)
inbound: Mar 18, 2018
7:45a SJU » 5:55p ORD
United Airlines 1 stop (10h10m)
$388
outward: Mar 17, 2018
1:45p ORD » 6:22p SJU
United Airlines direct (4h37m)
inbound: Mar 24, 2018
7:17p SJU » 12:27a ORD
United Airlines direct (5h10m)
$389
outward: Aug 23, 2018
12:55a ORD » 9:47a SJU
JetBlue 1 stop (8h52m)
inbound: Aug 27, 2018
8:12p SJU » 3:05a ORD
Spirit Airlines 1 stop (6h53m)
$389
outward: Jan 22, 2018
1:00p ORD » 8:44p SJU
Unknown Company 1 stop (7h44m)
inbound: Jan 25, 2018
10:44p SJU » 6:58a ORD
Spirit Airlines 1 stop (8h14m)
$397
outward: Dec 1, 2018
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)
inbound: Dec 9, 2018
12:40p SJU » 7:54p ORD
American Airlines 1 stop (7h14m)
$415
outward: Jun 28, 2018
2:30p MDW » 8:27p SJU
Unknown Airline 1 stop (5h57m)
inbound: Jul 7, 2018
1:00p SJU » 10:25p MDW
Unknown Airline 1 stop (9h25m)
$421
outward: Jan 21, 2018
11:25p ORD » 7:12p SJU
Spirit Airlines 2 stops (19h47m)
inbound: Jan 25, 2018
10:44p SJU » 5:55a ORD
Spirit Airlines 2 stops (31h11m)
$425
outward: Mar 6, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 14, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 6, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 15, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 6, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 16, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 7, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 14, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 7, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 16, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 8, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 14, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 8, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 15, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$425
outward: Mar 8, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 16, 2018
9:28p SJU » 5:52a ORD
Spirit Airlines 1 stop (8h24m)
$428
outward: Mar 8, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 19, 2018
9:37p SJU » 5:56a ORD
Spirit Airlines 1 stop (8h19m)
$428
outward: Mar 9, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 19, 2018
9:37p SJU » 5:56a ORD
Spirit Airlines 1 stop (8h19m)
$428
outward: Mar 8, 2018
12:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (7h01m)
inbound: Mar 19, 2018
9:37p SJU » 5:56a ORD
Spirit Airlines 1 stop (8h19m)
Return
Departure
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06 February Feb Tuesday $retDate.dayShortName
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27 January Jan Saturday $outDate.dayShortName
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$427 Spirit Airlines
1517310900000 ORD » 1517335920000 SJU, 1 (417)
1517953440000 SJU » 1517983080000 ORD, 1 (494)
$427 Spirit Airlines
1517310900000 ORD » 1517335920000 SJU, 1 (417)
1518039840000 SJU » 1518069480000 ORD, 1 (494)
$427 Spirit Airlines
1517310900000 ORD » 1517335920000 SJU, 1 (417)
1518126240000 SJU » 1518155880000 ORD, 1 (494)
31 January Jan Wednesday $outDate.dayShortName
$427 Spirit Airlines
1517397300000 ORD » 1517422320000 SJU, 1 (417)
1517953440000 SJU » 1517983080000 ORD, 1 (494)
$245 Multiple Airlines - Spirit Airlines
1517432700000 ORD » 1517513400000 SJU, 1 (1345)
1518039840000 SJU » 1518069480000 ORD, 1 (494)
$427 Spirit Airlines
1517397300000 ORD » 1517422320000 SJU, 1 (417)
1518126240000 SJU » 1518155880000 ORD, 1 (494)
01 February Feb Thursday $outDate.dayShortName
$427 Spirit Airlines
1517483700000 ORD » 1517508720000 SJU, 1 (417)
1517953440000 SJU » 1517983080000 ORD, 1 (494)
$427 Spirit Airlines
1517483700000 ORD » 1517508720000 SJU, 1 (417)
1518039840000 SJU » 1518069480000 ORD, 1 (494)
$427 Spirit Airlines
1517483700000 ORD » 1517508720000 SJU, 1 (417)
1518126240000 SJU » 1518155880000 ORD, 1 (494)
02 February Feb Friday $outDate.dayShortName
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: New York - San Juan London - San Juan Miami - San Juan See more routes

Airlines operating flights from Chicago to San Juan

  • any
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • all
  • American Airlines
  • JetBlue
  • Southwest Airlines
  • United Airlines
JetBlue
outbound: Feb 10, 2018
JetBlue 1 stop
return: Feb 28, 2018
JetBlue 1 stop
Southwest Airlines
outbound: Feb 10, 2018
Southwest Airlines 1 stop
return: Feb 28, 2018
Southwest Airlines 1 stop
United Airlines
outbound: Apr 5, 2018
United Airlines 1 stop
return: Apr 28, 2018
Spirit Airlines 1 stop
American Airlines
outbound: Jan 19, 2018
American Airlines 1 stop
return: Jan 21, 2018
American Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 8h27m (flight with stopovers)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Jan 17, 2018 1:52 PM, GMT-4
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jan 17, 2018 11:52 AM, GMT-6

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!