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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
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • any
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • price
  • month of departure
  • month of return
$195
outward: Sep 19, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 26, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$195
outward: Sep 19, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 27, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$195
outward: Sep 19, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 28, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$195
outward: Sep 20, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 26, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$195
outward: Sep 20, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 27, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$195
outward: Sep 20, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 28, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$200
outward: Sep 4, 2018
2:35p ORD » 7:13p SJU
Spirit Airlines 1 stop (28h38m)
inbound: Sep 18, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
14 days ago
$215
outward: Sep 4, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 18, 2018
8:22p SJU » 3:03a ORD
Spirit Airlines 1 stop (6h41m)
Verify
20 days ago
$216
outward: Aug 28, 2018
4:40p ORD » 3:16a SJU
Spirit Airlines 1 stop (10h36m)
inbound: Sep 11, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
20 days ago
$233
outward: Sep 21, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 26, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$233
outward: Sep 21, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 27, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$233
outward: Sep 21, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Sep 28, 2018
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
13 days ago
$236
outward: Aug 22, 2018
4:40p ORD » 3:16a SJU
Spirit Airlines 1 stop (10h36m)
inbound: Aug 29, 2018
10:42p SJU » 7:13a ORD
Spirit Airlines 1 stop (8h31m)
Verify
20 days ago
$249
outward: Oct 4, 2018
2:50p ORD » 7:41p SJU
United Airlines direct (4h51m)
inbound: Oct 7, 2018
1:00p SJU » 8:50p ORD
Delta Air Lines 1 stop (7h50m)
Verify
5 days ago
$271
outward: Oct 4, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Oct 7, 2018
10:40p SJU » 5:22p ORD
Spirit Airlines 1 stop (18h42m)
Verify
13 days ago
$289
outward: Oct 4, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Oct 7, 2018
10:40p SJU » 5:22p ORD
Spirit Airlines 1 stop (18h42m)
Verify
5 days ago
$290
outward: Oct 20, 2018
4:35a ORD » 7:18p SJU
Spirit Airlines 1 stop (14h43m)
inbound: Oct 29, 2018
9:40p SJU » 6:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
21 days ago
$337
outward: Apr 20, 2019
6:00a ORD » 10:45a SJU
United Airlines direct (4h45m)
inbound: Apr 23, 2019
10:45p SJU » 7:10a ORD
United Airlines 1 stop (8h25m)
Verify
3 days ago
$354
outward: Aug 27, 2018
4:40p ORD » 8:11a SJU
Spirit Airlines 1 stop (15h31m)
inbound: Aug 31, 2018
10:42p SJU » 7:13a ORD
Spirit Airlines 1 stop (8h31m)
Verify
7 days ago
$354
outward: Aug 27, 2018
4:40p ORD » 8:11a SJU
Spirit Airlines 1 stop (15h31m)
inbound: Aug 31, 2018
10:42p SJU » 7:13a ORD
Spirit Airlines 1 stop (8h31m)
Verify
7 days ago
$357
outward: Apr 19, 2019
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)
inbound: Apr 23, 2019
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)
Verify
20 days ago
$358
outward: Nov 23, 2018
12:45p ORD » 7:27a SJU
JetBlue 1 stop (18h42m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
20 days ago
$358
outward: Nov 23, 2018
12:45p ORD » 7:27a SJU
JetBlue 1 stop (18h42m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
20 days ago
$358
outward: Nov 23, 2018
12:45p ORD » 7:27a SJU
JetBlue 1 stop (18h42m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
20 days ago
$362
outward: May 11, 2019
10:30p ORD » 3:25a SJU
American Airlines direct (4h55m)
inbound: May 19, 2019
1:30p SJU » 6:32p ORD
American Airlines direct (5h02m)
Verify
5 days ago
$382
outward: Nov 24, 2018
2:54p ORD » 7:35p SJU
United Airlines direct (4h41m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
13 days ago
$383
outward: Nov 24, 2018
4:33a ORD » 5:52p SJU
United Airlines 1 stop (13h19m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
14 days ago
$385
outward: Nov 24, 2018
4:33a ORD » 5:52p SJU
United Airlines 1 stop (13h19m)
inbound: Dec 1, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
13 days ago
$389
outward: Nov 24, 2018
2:54p ORD » 7:35p SJU
United Airlines direct (4h41m)
inbound: Dec 1, 2018
1:00p SJU » 7:17p MDW
Delta Air Lines 1 stop (6h17m)
Verify
5 days ago
$399
outward: Dec 19, 2018
2:00p ORD » 7:32a SJU
JetBlue 1 stop (17h32m)
inbound: Jan 9, 2019
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
13 days ago
Return
Departure
Availability of fares is not guaranteed for offers found in the last 7 days.
Choose when you'd like to depart to San Juan (Puerto Rico):
*Best price per person, all taxes and surcharges included; found in the last 14 days on liligo.com
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
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • all
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 27, 2018
Spirit Airlines 1 stop
return: Aug 31, 2018
Spirit Airlines 1 stop
$354 Verify
7 days ago
United Airlines
outbound: Aug 27, 2018
United Airlines direct
return: Aug 31, 2018
United Airlines direct
$580 Verify
7 days ago
Airline tickets Chicago - San Juan found in the last 30 days.

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 4h55m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Aug 19, 2018 9:12 PM, GMT-4
  • Weather:
  • min. 47ºF, max. 62ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Aug 19, 2018 8:12 PM, GMT-5
  • Weather:
  • min. 65ºF, max. 76ºF

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!