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
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • any
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • price
  • month of departure
  • month of return
$163
Spirit Airlines outward: Sep 6, 2020
1:28a ORD » 7:16p SJU
Spirit Airlines 1 stop (17h48m)
Spirit Airlines inbound: Sep 19, 2020
8:11p SJU » 7:14a ORD
Spirit Airlines 1 stop (11h03m)
$163
Spirit Airlines outward: Sep 6, 2020
1:28a ORD » 7:16p SJU
Spirit Airlines 1 stop (17h48m)
Spirit Airlines inbound: Sep 19, 2020
8:11p SJU » 2:44a ORD
Spirit Airlines 1 stop (6h33m)
$181
Spirit Airlines outward: Jul 18, 2020
3:14a ORD » 4:54p SJU
Spirit Airlines 1 stop (13h40m)
Unknown Company inbound: Jul 21, 2020
3:55a SJU » 11:36p ORD
Unknown Company 1 stop (19h41m)
$190
Spirit Airlines outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)
Spirit Airlines inbound: Jul 21, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)
$190
Spirit Airlines outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)
Spirit Airlines inbound: Jul 21, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)
$190
Spirit Airlines outward: Jul 14, 2020
3:14p ORD » 8:13a SJU
Spirit Airlines 1 stop (16h59m)
Spirit Airlines inbound: Jul 22, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)
$212
Spirit Airlines outward: Jul 20, 2020
4:11p ORD » 2:51a SJU
Spirit Airlines 1 stop (10h40m)
Spirit Airlines inbound: Jul 27, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)
$241
Spirit Airlines outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)
Unknown Company inbound: Jul 21, 2020
3:18a SJU » 7:40p ORD
Unknown Company 1 stop (16h22m)
$289
American Airlines outward: Dec 31, 2020
6:45p ORD » 4:09a SJU
American Airlines 1 stop (9h24m)
American Airlines inbound: Jan 12, 2021
8:17p SJU » 1:50a ORD
American Airlines direct (5h33m)
$530
Frontier Airlines outward: Dec 21, 2020
4:45p ORD » 9:36p SJU
Frontier Airlines direct (4h51m)
Frontier Airlines inbound: Jan 2, 2021
12:39a SJU » 6:20a ORD
Frontier Airlines direct (5h41m)
Return
Departure
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
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • all
  • American Airlines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 13, 2020
Spirit Airlines 1 stop
return: Jul 21, 2020
Spirit Airlines 1 stop
American Airlines
outbound: Sep 5, 2020
American Airlines 1 stop
return: Sep 19, 2020
American Airlines 2 stops
United Airlines
outbound: Dec 31, 2020
United Airlines 1 stop
return: Jan 12, 2021
United Airlines 1 stop
Frontier Airlines
outbound: Dec 31, 2020
Frontier Airlines direct
return: Jan 12, 2021
United Airlines direct

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 9h47m (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:
  • Jul 11, 2020 9:41 AM, GMT-4
  • Weather:
  • min. 41ºF, max. 59ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 11, 2020 8:41 AM, GMT-5
  • Weather:
  • min. 72ºF, max. 80ºF

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!