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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
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • any
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • price
  • month of departure
  • month of return
$184
outward: Aug 29, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 5, 2018
10:42p SJU » 7:13a ORD
Spirit Airlines 1 stop (8h31m)
Verify
18 days ago
$190
outward: Aug 29, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 5, 2018
10:42p SJU » 7:13a ORD
Spirit Airlines 1 stop (8h31m)
Verify
23 days ago
$223
outward: Aug 2, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 8, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$223
outward: Aug 2, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 7, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$228
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
19 days ago
$228
outward: Aug 29, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 12, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
19 days ago
$228
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
19 days ago
$229
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
18 days ago
$229
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
18 days ago
$229
outward: Aug 29, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 12, 2018
9:20p SJU » 2:15a MDW
Southwest Airlines direct (4h55m)
Verify
18 days ago
$238
outward: Aug 3, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 7, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$238
outward: Jun 27, 2018
1:15a ORD » 8:28a SJU
Frontier Airlines direct (7h13m)
inbound: Jul 2, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$238
outward: Jun 28, 2018
1:15a ORD » 8:28a SJU
Frontier Airlines direct (7h13m)
inbound: Jul 2, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$238
outward: Aug 2, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 5, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$238
outward: Jul 5, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Jul 9, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$238
outward: Jul 6, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 7, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
18 days ago
$241
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
10:40p SJU » 6:55a ORD
Spirit Airlines 1 stop (8h15m)
Verify
23 days ago
$241
outward: Aug 28, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 11, 2018
10:40p SJU » 6:55a ORD
Spirit Airlines 1 stop (8h15m)
Verify
22 days ago
$241
outward: Aug 29, 2018
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)
inbound: Sep 12, 2018
10:40p SJU » 6:55a ORD
Spirit Airlines 1 stop (8h15m)
Verify
22 days ago
$242
outward: Jul 18, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 7, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
11 days ago
$242
outward: Jul 18, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 8, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
11 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 7, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
11 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 8, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
11 days ago
$242
outward: Jul 18, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 1, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
10 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 1, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
10 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 1, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
10 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 1, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
9 days ago
$242
outward: Aug 2, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 8, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
9 days ago
$242
outward: Jul 19, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 1, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
8 days ago
$242
outward: Aug 2, 2018
12:57a ORD » 8:39a SJU
Frontier Airlines direct (7h42m)
inbound: Aug 8, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines direct (8h32m)
Verify
8 days ago
Return
Departure
06 July Jul Friday $retDate.dayShortName
07 July Jul Saturday $retDate.dayShortName
08 July Jul Sunday $retDate.dayShortName
09 July Jul Monday $retDate.dayShortName
10 July Jul Tuesday $retDate.dayShortName
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12 July Jul Thursday $retDate.dayShortName
30 June Jun Saturday $outDate.dayShortName
$358 $356
01 July Jul Sunday $outDate.dayShortName
$366 $379 $344
02 July Jul Monday $outDate.dayShortName
$419
03 July Jul Tuesday $outDate.dayShortName
$325 $349
04 July Jul Wednesday $outDate.dayShortName
$332 $332 $277 $328
05 July Jul Thursday $outDate.dayShortName
$292 $292 $237 $283 $331
06 July Jul Friday $outDate.dayShortName
$307 $307 $252
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
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • all
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Sep 12, 2018
Spirit Airlines 1 stop
return: Sep 17, 2018
Spirit Airlines 1 stop
$272 Verify
10 days ago
JetBlue
outbound: Sep 12, 2018
JetBlue 1 stop
return: Sep 17, 2018
JetBlue 1 stop
$293 Verify
10 days ago
Southwest Airlines
outbound: Dec 16, 2018
Southwest Airlines direct
return: Dec 23, 2018
Southwest Airlines 2 stops
$460 Verify
10 days ago
Frontier Airlines
outbound: Jul 27, 2018
Frontier Airlines 1 stop
return: Jul 31, 2018
Frontier Airlines 1 stop
$258 Verify
13 days ago
United Airlines
outbound: Sep 13, 2018
United Airlines direct
return: Sep 17, 2018
United Airlines direct
$344 Verify
10 days ago
American Airlines
outbound: Apr 27, 2019
American Airlines direct
return: May 5, 2019
American Airlines direct
$410 Verify
13 days ago
Delta Air Lines
outbound: Dec 27, 2018
Delta Air Lines 1 stop
return: Jan 3, 2019
Delta Air Lines 1 stop
$707 Verify
10 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: 8h02m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Jun 25, 2018 11:43 AM, GMT-4
  • Weather:
  • min. 49ºF, max. 65ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 25, 2018 10:43 AM, GMT-5
  • Weather:
  • min. 68ºF, max. 77ºF

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!