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 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • any
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • price
  • month of departure
  • month of return
$135
Spirit Airlines outward: Mar 3, 2020
12:15p ORD » 7:19p SJU
Spirit Airlines 1 stop (7h04m)
Spirit Airlines inbound: Mar 11, 2020
9:28p SJU » 4:22a ORD
Spirit Airlines 1 stop (6h54m)
$146
Spirit Airlines outward: Mar 3, 2020
12:15p ORD » 7:19p SJU
Spirit Airlines 1 stop (7h04m)
Spirit Airlines inbound: Mar 11, 2020
7:15p SJU » 5:52a ORD
Spirit Airlines 1 stop (10h37m)
$169
Spirit Airlines outward: Mar 3, 2020
2:00p ORD » 6:52a SJU
Spirit Airlines 1 stop (16h52m)
Spirit Airlines inbound: Mar 11, 2020
7:15p SJU » 5:52a ORD
Spirit Airlines 1 stop (10h37m)
$177
Spirit Airlines outward: Feb 10, 2020
2:00p ORD » 6:50a SJU
Spirit Airlines 1 stop (16h50m)
Spirit Airlines inbound: Feb 28, 2020
6:51p SJU » 6:21a ORD
Spirit Airlines 1 stop (11h30m)
$198
Spirit Airlines outward: Feb 10, 2020
6:00p ORD » 5:27a SJU
Spirit Airlines 1 stop (11h27m)
Spirit Airlines inbound: Feb 28, 2020
11:00a SJU » 5:25p ORD
Spirit Airlines 1 stop (30h25m)
$203
Spirit Airlines outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)
Spirit Airlines inbound: Feb 9, 2020
2:45a SJU » 10:16p ORD
Spirit Airlines 2 stops (19h31m)
$227
Spirit Airlines outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)
Spirit Airlines inbound: Feb 8, 2020
3:35p SJU » 4:44a ORD
Spirit Airlines 1 stop (13h09m)
$255
Frontier Airlines outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)
Frontier Airlines inbound: Jun 25, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)
$262
Spirit Airlines outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)
Spirit Airlines inbound: Feb 8, 2020
6:30a SJU » 5:28p ORD
Spirit Airlines 1 stop (10h58m)
$287
Frontier Airlines outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)
Frontier Airlines inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)
$287
Frontier Airlines outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)
Frontier Airlines inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)
$290
Frontier Airlines outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)
Frontier Airlines inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)
$306
Frontier Airlines outward: Mar 5, 2020
3:01p ORD » 10:13p SJU
Frontier Airlines 1 stop (7h12m)
Unknown Company inbound: Mar 8, 2020
11:00a SJU » 4:10p ORD
Unknown Company 1 stop (29h10m)
$308
Frontier Airlines outward: Mar 5, 2020
3:01p ORD » 8:00a SJU
Frontier Airlines 1 stop (16h59m)
Unknown Company inbound: Mar 8, 2020
10:13p SJU » 2:07p ORD
Unknown Company 1 stop (15h54m)
$331
JetBlue outward: Mar 5, 2020
2:17p ORD » 8:24a SJU
JetBlue 1 stop (18h07m)
JetBlue inbound: Mar 9, 2020
4:45a SJU » 6:49a ORD
JetBlue 1 stop (26h04m)
$332
JetBlue outward: Apr 9, 2020
2:30p ORD » 2:35a SJU
JetBlue 1 stop (12h05m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$337
JetBlue outward: Aug 17, 2020
12:09p ORD » 6:27p SJU
JetBlue 1 stop (6h18m)
Spirit Airlines inbound: Aug 22, 2020
5:59a SJU » 4:13p ORD
Spirit Airlines 1 stop (10h14m)
$347
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$348
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$351
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)
JetBlue inbound: Apr 13, 2020
2:15p SJU » 7:49a ORD
JetBlue 1 stop (17h34m)
$353
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)
$353
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)
$353
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)
$353
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)
$358
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)
JetBlue inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)
$364
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$365
JetBlue outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$365
JetBlue outward: Apr 9, 2020
2:30p ORD » 2:12a SJU
JetBlue 1 stop (11h42m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$370
JetBlue outward: Apr 9, 2020
2:30p ORD » 2:12a SJU
JetBlue 1 stop (11h42m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
$371
JetBlue outward: Apr 9, 2020
2:30p ORD » 12:57a SJU
JetBlue 1 stop (10h27m)
JetBlue inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)
Return
Departure
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
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • all
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • United Airlines
JetBlue
outbound: Aug 17, 2020
JetBlue 1 stop
return: Aug 21, 2020
Spirit Airlines 1 stop
American Airlines
outbound: Aug 17, 2020
American Airlines 1 stop
return: Aug 21, 2020
Spirit Airlines 1 stop
Frontier Airlines
outbound: Aug 17, 2020
Frontier Airlines direct
return: Aug 21, 2020
American Airlines 1 stop
United Airlines
outbound: Aug 17, 2020
United Airlines direct
return: Aug 21, 2020
United Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 12h47m (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 25, 2020 6:43 PM, GMT-4
  • Weather:
  • min. 83ºF, max. 97ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jan 25, 2020 4:43 PM, GMT-6
  • Weather:
  • min. 31ºF, max. 34ºF

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!