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
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • any
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • price
  • month of departure
  • month of return
$99
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
Spirit Airlines inbound: Oct 29, 2020
12:00p SJU » 11:31p ORD
Spirit Airlines 1 stop (11h31m)
$99
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
Spirit Airlines inbound: Oct 29, 2020
12:00p SJU » 11:31p ORD
Spirit Airlines 1 stop (11h31m)
$99
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
Spirit Airlines inbound: Oct 29, 2020
12:00p SJU » 11:31p ORD
Spirit Airlines 1 stop (11h31m)
$113
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
12:00p SJU » 11:31p ORD
Spirit Airlines 1 stop (11h31m)
$114
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
Unknown Company inbound: Oct 29, 2020
12:00p SJU » 8:21p ORD
Unknown Company 1 stop (8h21m)
$117
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
3:54p SJU » 3:23a ORD
Spirit Airlines 1 stop (11h29m)
$121
Spirit Airlines outward: Oct 22, 2020
12:30p ORD » 7:16p SJU
Spirit Airlines 1 stop (6h46m)
Spirit Airlines inbound: Oct 29, 2020
7:11p SJU » 1:44a ORD
Spirit Airlines 1 stop (6h33m)
$121
Spirit Airlines outward: Oct 23, 2020
1:36a ORD » 8:30a SJU
Spirit Airlines 1 stop (6h54m)
Spirit Airlines inbound: Oct 29, 2020
8:30a SJU » 3:48p ORD
Spirit Airlines 1 stop (7h18m)
$121
Spirit Airlines outward: Oct 22, 2020
4:15p ORD » 7:16p SJU
Spirit Airlines 1 stop (27h01m)
Spirit Airlines inbound: Oct 29, 2020
8:30a SJU » 1:44a ORD
Spirit Airlines 1 stop (17h14m)
$121
Spirit Airlines outward: Oct 22, 2020
12:30p ORD » 8:30a SJU
Spirit Airlines 1 stop (20h)
Spirit Airlines inbound: Oct 29, 2020
7:11p SJU » 6:14a ORD
Spirit Airlines 1 stop (11h03m)
$121
Spirit Airlines outward: Oct 23, 2020
1:36a ORD » 8:30a SJU
Spirit Airlines 1 stop (6h54m)
Spirit Airlines inbound: Oct 29, 2020
7:11p SJU » 6:14a ORD
Spirit Airlines 1 stop (11h03m)
$121
Spirit Airlines outward: Oct 22, 2020
4:15p ORD » 8:30a SJU
Spirit Airlines 1 stop (16h15m)
Spirit Airlines inbound: Oct 29, 2020
4:52p SJU » 2:49a ORD
Spirit Airlines 1 stop (9h57m)
$121
Spirit Airlines outward: Oct 22, 2020
12:30p ORD » 7:16p SJU
Spirit Airlines 1 stop (6h46m)
Spirit Airlines inbound: Oct 30, 2020
4:59a SJU » 3:13p ORD
Spirit Airlines 1 stop (10h14m)
$121
Spirit Airlines outward: Oct 23, 2020
1:36a ORD » 8:30a SJU
Spirit Airlines 1 stop (6h54m)
Spirit Airlines inbound: Oct 29, 2020
7:11p SJU » 3:48p ORD
Spirit Airlines 1 stop (20h37m)
$121
Spirit Airlines outward: Oct 22, 2020
12:30p ORD » 7:16p SJU
Spirit Airlines 1 stop (6h46m)
Spirit Airlines inbound: Oct 29, 2020
7:11p SJU » 6:14a ORD
Spirit Airlines 1 stop (11h03m)
$121
Spirit Airlines outward: Oct 23, 2020
1:36a ORD » 8:30a SJU
Spirit Airlines 1 stop (6h54m)
Spirit Airlines inbound: Oct 29, 2020
8:30a SJU » 3:48p ORD
Spirit Airlines 1 stop (7h18m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
3:54p SJU » 3:23a ORD
Spirit Airlines 1 stop (11h29m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
7:39p SJU » 3:23a ORD
Spirit Airlines 1 stop (7h44m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
3:54p SJU » 3:23a ORD
Spirit Airlines 1 stop (11h29m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
3:54p SJU » 3:23a ORD
Spirit Airlines 1 stop (11h29m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
7:39p SJU » 3:23a ORD
Spirit Airlines 1 stop (7h44m)
$122
Spirit Airlines outward: Oct 22, 2020
2:20p ORD » 8:42p SJU
Spirit Airlines 1 stop (6h22m)
Spirit Airlines inbound: Oct 29, 2020
7:39p SJU » 3:23a ORD
Spirit Airlines 1 stop (7h44m)
$123
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
Unknown Company inbound: Oct 29, 2020
12:00p SJU » 8:21p ORD
Unknown Company 1 stop (8h21m)
$123
Spirit Airlines outward: Oct 22, 2020
1:00p ORD » 3:17a SJU
Spirit Airlines 1 stop (14h17m)
JetBlue inbound: Oct 29, 2020
11:01a SJU » 8:56p ORD
JetBlue 1 stop (9h55m)
$128
Spirit Airlines outward: Oct 22, 2020
11:45p ORD » 3:17a SJU
Spirit Airlines 1 stop (27h32m)
JetBlue inbound: Oct 29, 2020
11:01a SJU » 8:56p ORD
JetBlue 1 stop (9h55m)
$128
Spirit Airlines outward: Oct 22, 2020
11:45p ORD » 3:17a SJU
Spirit Airlines 1 stop (27h32m)
JetBlue inbound: Oct 29, 2020
11:01a SJU » 8:56p ORD
JetBlue 1 stop (9h55m)
$141
Unknown Company outward: Oct 22, 2020
1:20p ORD » 9:56p SJU
Unknown Company 1 stop (8h36m)
Frontier Airlines inbound: Oct 29, 2020
1:00p SJU » 2:08a ORD
Frontier Airlines 1 stop (13h08m)
$150
Unknown Company outward: Dec 4, 2020
4:05a ORD » 6:31p SJU
Unknown Company 1 stop (14h26m)
Spirit Airlines inbound: Dec 7, 2020
6:10a SJU » 4:13p ORD
Spirit Airlines 1 stop (10h03m)
$238
JetBlue outward: Nov 28, 2020
12:55p ORD » 2:10a SJU
JetBlue 1 stop (13h15m)
JetBlue inbound: Dec 5, 2020
12:00p SJU » 6:34a ORD
JetBlue 1 stop (18h34m)
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
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • all
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Dec 3, 2020
Spirit Airlines 1 stop
return: Dec 7, 2020
Spirit Airlines 1 stop
JetBlue
outbound: Nov 28, 2020
JetBlue 1 stop
return: Dec 5, 2020
JetBlue 1 stop
United Airlines
outbound: Dec 3, 2020
United Airlines 1 stop
return: Dec 7, 2020
Spirit Airlines 1 stop
American Airlines
outbound: Nov 28, 2020
American Airlines direct
return: Dec 5, 2020
American Airlines 1 stop
Frontier Airlines
outbound: Nov 28, 2020
Frontier Airlines direct
return: Dec 5, 2020
Spirit Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 12h35m (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:
  • Sep 19, 2020 1:44 AM, GMT-4
  • Weather:
  • min. 46ºF, max. 68ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 19, 2020 12:44 AM, GMT-5
  • Weather:
  • min. 55ºF, max. 65ºF

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!