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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
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • any
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • price
  • month of departure
  • month of return
$235
outward: Oct 23, 2018
12:15p ORD » 7:18p SJU
Spirit Airlines 1 stop (7h03m)
inbound: Oct 30, 2018
9:40p SJU » 6:16a ORD
Spirit Airlines 1 stop (8h36m)
Verify
21 days ago
$285
outward: Nov 19, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 11, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$292
outward: Nov 19, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 10, 2018
10:28p SJU » 4:58p ORD
Spirit Airlines 1 stop (18h30m)
Verify
21 days ago
$295
outward: Nov 20, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 11, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$324
outward: Nov 18, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 11, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$328
outward: Oct 21, 2018
4:35a ORD » 6:20p SJU
United Airlines 1 stop (13h45m)
inbound: Oct 28, 2018
9:42p SJU » 3:37a ORD
Unknown Company 1 stop (29h55m)
Verify
16 days ago
$333
outward: Nov 20, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 10, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$362
outward: Nov 18, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 10, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$364
outward: Nov 19, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 9, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$374
outward: Nov 20, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 9, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$404
outward: Nov 18, 2018
12:15p ORD » 7:14p SJU
Spirit Airlines 1 stop (6h59m)
inbound: Dec 9, 2018
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)
Verify
21 days ago
$458
outward: Jan 2, 2019
1:20a ORD » 8:26a SJU
Spirit Airlines 1 stop (7h06m)
inbound: Jan 9, 2019
3:07a SJU » 6:39a ORD
JetBlue 1 stop (27h32m)
Verify
22 days ago
$460
outward: Oct 20, 2018
5:15p ORD » 4:18a SJU
United Airlines 1 stop (11h03m)
inbound: Oct 28, 2018
9:00a SJU » 4:22p ORD
Unknown Company 1 stop (7h22m)
Verify
3 days ago
$490
outward: Jan 2, 2019
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 9, 2019
12:39a SJU » 5:01p ORD
Spirit Airlines 1 stop (16h22m)
Verify
25 days ago
$495
outward: Apr 11, 2019
3:28p ORD » 8:48p SJU
Unknown Company 1 stop (29h20m)
inbound: Apr 21, 2019
11:40a SJU » 4:50p ORD
United Airlines direct (5h10m)
Verify
5 days ago
$559
outward: Dec 17, 2018
11:30p ORD » 8:29a SJU
Spirit Airlines 2 stops (8h59m)
inbound: Dec 30, 2018
5:40p SJU » 12:43a ORD
Spirit Airlines 1 stop (7h03m)
Verify
3 days ago
$604
outward: Dec 22, 2018
3:45p ORD » 7:51a SJU
United Airlines 1 stop (16h06m)
inbound: Jan 10, 2019
7:01a SJU » 4:16p ORD
United Airlines 1 stop (9h15m)
Verify
22 days ago
$711
outward: Dec 24, 2018
1:35a ORD » 7:59a SJU
Spirit Airlines 1 stop (6h24m)
inbound: Jan 3, 2019
9:30a SJU » 4:55p ORD
Spirit Airlines 1 stop (7h25m)
Verify
12 days ago
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$403 $362 $324
19 November Nov Monday $outDate.dayShortName
$363 $291 $284
20 November Nov Tuesday $outDate.dayShortName
$373 $333 $294
21 November Nov Wednesday $outDate.dayShortName
Availability of fares is not guaranteed for offers found in the last 7 days.
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 See more routes

Airlines operating flights from Chicago to San Juan

  • any
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • all
  • American Airlines
  • Delta Air Lines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Nov 19, 2018
Spirit Airlines 1 stop
return: Dec 10, 2018
Spirit Airlines 1 stop
$298 Verify
21 days ago
American Airlines
outbound: Nov 19, 2018
American Airlines direct
return: Dec 10, 2018
American Airlines direct
$371 Verify
21 days ago
United Airlines
outbound: Nov 19, 2018
United Airlines 1 stop
return: Dec 10, 2018
United Airlines 1 stop
$435 Verify
21 days ago
Delta Air Lines
outbound: Dec 22, 2018
Delta Air Lines 1 stop
return: Jan 10, 2019
Delta Air Lines 1 stop
$831 Verify
22 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: 8h18m (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:
  • Oct 17, 2018 3:14 AM, GMT-4
  • Weather:
  • min. 61ºF, max. 82ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 17, 2018 2:14 AM, GMT-5
  • Weather:
  • min. 38ºF, max. 50ºF

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!