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Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$299

outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)

inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)

$302

outward: Aug 20, 2019
2:49p ORD » 10:36p SJU
Frontier Airlines 1 stop (7h47m)

inbound: Aug 27, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$303

outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)

inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)

$304

outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)

inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)

$304

outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)

inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)

$304

outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)

inbound: Nov 12, 2019
8:59a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h48m)

$310

outward: Aug 21, 2019
2:02p ORD » 10:42p SJU
JetBlue 1 stop (8h40m)

inbound: Aug 28, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$323

outward: Jul 5, 2019
2:02p ORD » 8:44p SJU
JetBlue direct (6h42m)

inbound: Jul 6, 2019
8:26a SJU » 4:34p ORD
JetBlue 1 stop (8h08m)

$328

outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)

inbound: Feb 8, 2020
3:55p SJU » 1:00a ORD
JetBlue 1 stop (9h05m)

$328

outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)

inbound: Feb 8, 2020
10:00p SJU » 6:42a ORD
JetBlue 1 stop (8h42m)

$328

outward: Jan 29, 2020
1:55p ORD » 1:36p SJU
JetBlue 1 stop (23h41m)

inbound: Feb 8, 2020
3:55p SJU » 1:00a ORD
JetBlue 1 stop (9h05m)

$333

outward: Dec 27, 2019
1:55p ORD » 1:50p SJU
JetBlue 1 stop (23h55m)

inbound: Jan 6, 2020
6:43a SJU » 3:41p ORD
JetBlue 1 stop (8h58m)

$339

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$339

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$339

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$339

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$340

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$341

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$341

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$341

outward: Oct 3, 2019
12:33p ORD » 7:41p SJU
JetBlue 1 stop (7h08m)

inbound: Oct 31, 2019
7:33a SJU » 6:06a ORD
JetBlue 1 stop (22h33m)

$348

outward: Sep 18, 2019
5:17p ORD » 9:22a SJU
JetBlue 1 stop (16h05m)

inbound: Sep 23, 2019
5:10p SJU » 6:39a ORD
JetBlue 1 stop (13h29m)

$349

outward: Jan 29, 2020
12:45p ORD » 7:23p SJU
American Airlines 1 stop (6h38m)

inbound: Feb 8, 2020
10:40p SJU » 6:28a ORD
American Airlines 1 stop (7h48m)

$351

outward: Jul 23, 2019
4:40p ORD » 3:10a SJU
Spirit Airlines 1 stop (10h30m)

inbound: Aug 20, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$351

outward: Nov 5, 2019
11:16p ORD » 6:54a SJU
Frontier Airlines 1 stop (7h38m)

inbound: Nov 19, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)

$351

outward: Nov 5, 2019
2:49p ORD » 10:43p SJU
Frontier Airlines 1 stop (7h54m)

inbound: Nov 20, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)

$351

outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)

inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$351

outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)

inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$351

outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)

inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$351

outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)

inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$352

outward: Aug 11, 2019
3:10p ORD » 6:15a SJU
United Airlines 1 stop (15h05m)

inbound: Aug 21, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

Return

Departure

	30 June Jun Sunday $retDate.dayShortName	01 July Jul Monday $retDate.dayShortName	02 July Jul Tuesday $retDate.dayShortName	03 July Jul Wednesday $retDate.dayShortName	04 July Jul Thursday $retDate.dayShortName	05 July Jul Friday $retDate.dayShortName	06 July Jul Saturday $retDate.dayShortName
18 June Jun Tuesday $outDate.dayShortName			$394	$416	$480
19 June Jun Wednesday $outDate.dayShortName			$425	$462
20 June Jun Thursday $outDate.dayShortName	$523	$526		$454
21 June Jun Friday $outDate.dayShortName	$514	$541					$443
22 June Jun Saturday $outDate.dayShortName							$454
23 June Jun Sunday $outDate.dayShortName
24 June Jun Monday $outDate.dayShortName							$452

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

Departure: Airline

JetBlue

outbound: Sep 6, 2019
JetBlue 1 stop

return: Sep 23, 2019
JetBlue 1 stop

Spirit Airlines

outbound: Sep 6, 2019
Spirit Airlines 1 stop

return: Sep 23, 2019
Spirit Airlines 1 stop

Southwest Airlines

outbound: Jun 21, 2019
Southwest Airlines 1 stop

return: Jul 15, 2019
Spirit Airlines 1 stop

Frontier Airlines

outbound: Jul 23, 2019
Frontier Airlines 1 stop

return: Jul 30, 2019
Frontier Airlines 1 stop

American Airlines

outbound: Nov 2, 2019
American Airlines 1 stop

return: Nov 10, 2019
Frontier Airlines 1 stop

United Airlines

outbound: Jul 26, 2019
United Airlines 1 stop

return: Aug 5, 2019
United Airlines 1 stop

Delta Air Lines

outbound: Sep 6, 2019
Delta Air Lines 1 stop

return: Sep 23, 2019
Spirit Airlines 1 stop

Air Canada

outbound: Dec 21, 2019
Air Canada 1 stop

return: Dec 29, 2019
Delta Air Lines 1 stop

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: 4h59m (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 17, 2019 4:41 AM, GMT-4
Weather:
min. 35ºF, max. 54ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Jun 17, 2019 3:41 AM, GMT-5
Weather:
min. 54ºF, max. 63ºF

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!

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