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Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$242

outward: Sep 18, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)

inbound: Sep 23, 2019
10:40p SJU » 7:16a ORD
Spirit Airlines 1 stop (8h36m)

$243

outward: Oct 3, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)

inbound: Oct 31, 2019
11:20a SJU » 2:05a ORD
Spirit Airlines 1 stop (14h45m)

$247

outward: Sep 18, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)

inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)

$252

outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)

inbound: Nov 16, 2019
9:30a SJU » 5:44p ORD
Spirit Airlines 1 stop (8h14m)

$253

outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)

inbound: Nov 16, 2019
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)

$258

outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)

inbound: Nov 16, 2019
9:30a SJU » 5:01p ORD
Spirit Airlines 1 stop (7h31m)

$259

outward: Sep 18, 2019
10:40p ORD » 5:59a SJU
Spirit Airlines 1 stop (7h19m)

inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)

$259

outward: Sep 24, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)

inbound: Oct 1, 2019
8:20a SJU » 5:37p ORD
Spirit Airlines 1 stop (9h17m)

$261

outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)

inbound: Nov 16, 2019
10:28p SJU » 6:59a ORD
Spirit Airlines 1 stop (8h31m)

$261

outward: Nov 13, 2019
10:24p ORD » 5:55a SJU
Spirit Airlines 1 stop (7h31m)

inbound: Nov 16, 2019
5:21p SJU » 6:59a ORD
Spirit Airlines 1 stop (13h38m)

$263

outward: Sep 28, 2019
11:50p ORD » 3:53p SJU
Spirit Airlines 1 stop (16h03m)

inbound: Oct 7, 2019
2:55a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h30m)

$263

outward: Jan 29, 2020
12:15p ORD » 4:08a SJU
Spirit Airlines 1 stop (15h53m)

inbound: Feb 9, 2020
4:59a SJU » 5:00p ORD
Spirit Airlines 1 stop (12h01m)

$264

outward: Sep 18, 2019
10:40p ORD » 5:59a SJU
Spirit Airlines 1 stop (7h19m)

inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)

$264

outward: Sep 28, 2019
11:50p ORD » 3:53p SJU
Spirit Airlines 1 stop (16h03m)

inbound: Oct 7, 2019
2:55a SJU » 8:25p ORD
Spirit Airlines 1 stop (17h30m)

$267

outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)

inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)

$267

outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)

inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)

$267

outward: Sep 25, 2019
2:49p ORD » 7:21a SJU
Frontier Airlines 1 stop (16h32m)

inbound: Oct 1, 2019
3:55a SJU » 9:47p ORD
Unknown Company 1 stop (17h52m)

$270

outward: Sep 28, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)

inbound: Oct 7, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)

$274

outward: Sep 28, 2019
4:30p ORD » 3:05a SJU
Spirit Airlines 1 stop (10h35m)

inbound: Oct 7, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)

$276

outward: Sep 18, 2019
4:30p ORD » 9:37p SJU
Spirit Airlines 1 stop (29h07m)

inbound: Sep 24, 2019
3:55a SJU » 3:07a ORD
Spirit Airlines 1 stop (23h12m)

$281

outward: Aug 21, 2019
2:49p ORD » 7:07a SJU
Frontier Airlines 1 stop (16h18m)

inbound: Aug 28, 2019
9:35a SJU » 9:48p ORD
Frontier Airlines 1 stop (12h13m)

$282

outward: Oct 3, 2019
4:30p ORD » 4:52a SJU
Spirit Airlines 1 stop (12h22m)

inbound: Oct 31, 2019
7:22p SJU » 1:49a ORD
Spirit Airlines 1 stop (6h27m)

$291

outward: Nov 13, 2019
12:15p ORD » 7:20p SJU
Spirit Airlines 1 stop (7h05m)

inbound: Nov 16, 2019
5:21p SJU » 6:59a ORD
Spirit Airlines 1 stop (13h38m)

$294

outward: Jan 30, 2020
12:23a ORD » 7:19a SJU
Frontier Airlines 1 stop (6h56m)

inbound: Feb 8, 2020
8:56a SJU » 4:08p ORD
Frontier Airlines 1 stop (7h12m)

$294

outward: Jan 29, 2020
2:00p ORD » 8:57p SJU
Frontier Airlines 1 stop (6h57m)

inbound: Feb 8, 2020
8:56a SJU » 4:08p ORD
Frontier Airlines 1 stop (7h12m)

$304

outward: Oct 3, 2019
12:15p ORD » 7:24p SJU
Spirit Airlines 1 stop (7h09m)

inbound: Oct 31, 2019
11:20a SJU » 2:05a ORD
Spirit Airlines 1 stop (14h45m)

$307

outward: Aug 30, 2019
11:08p ORD » 6:26p SJU
Spirit Airlines 1 stop (19h18m)

inbound: Sep 9, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)

$318

outward: Nov 13, 2019
4:24p ORD » 9:28p SJU
Spirit Airlines 1 stop (29h04m)

inbound: Nov 17, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 2 stops (19h24m)

$318

outward: Aug 31, 2019
4:40a ORD » 9:31p SJU
Unknown Company 1 stop (16h51m)

inbound: Sep 9, 2019
2:55a SJU » 7:41p ORD
Spirit Airlines 1 stop (16h46m)

$320

outward: Nov 13, 2019
4:27p ORD » 9:28p SJU
Spirit Airlines 1 stop (29h01m)

inbound: Nov 16, 2019
8:03p SJU » 2:58p ORD
Spirit Airlines 1 stop (18h55m)

Return

Departure

	01 January Jan Wednesday $retDate.dayShortName	02 January Jan Thursday $retDate.dayShortName	03 January Jan Friday $retDate.dayShortName	04 January Jan Saturday $retDate.dayShortName	05 January Jan Sunday $retDate.dayShortName	06 January Jan Monday $retDate.dayShortName	07 January Jan Tuesday $retDate.dayShortName
20 December Dec Friday $outDate.dayShortName					$771
21 December Dec Saturday $outDate.dayShortName
22 December Dec Sunday $outDate.dayShortName					$800
23 December Dec Monday $outDate.dayShortName	$391		$600	$598			$662
24 December Dec Tuesday $outDate.dayShortName
25 December Dec Wednesday $outDate.dayShortName				$623
26 December Dec Thursday $outDate.dayShortName		$721		$862	$764

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

Spirit Airlines

outbound: Aug 23, 2019
Spirit Airlines 1 stop

return: Aug 26, 2019
Spirit Airlines 1 stop

Southwest Airlines

outbound: Nov 4, 2019
Southwest Airlines 1 stop

return: Dec 2, 2019
Spirit Airlines 1 stop

JetBlue

outbound: Dec 17, 2019
JetBlue 1 stop

return: Jan 7, 2020
JetBlue 1 stop

Frontier Airlines

outbound: Aug 23, 2019
Frontier Airlines 1 stop

return: Aug 26, 2019
Spirit Airlines 1 stop

United Airlines

outbound: Aug 23, 2019
United Airlines direct

return: Aug 26, 2019
United Airlines 1 stop

Air New Zealand

outbound: Dec 26, 2019
Air New Zealand direct

return: Dec 29, 2019
Air Canada 1 stop

American Airlines

outbound: Dec 18, 2019
American Airlines 1 stop

return: Jan 7, 2020
Frontier Airlines 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: 5h22m (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 20, 2019 11:59 AM, GMT-4
Weather:
min. 39ºF, max. 65ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Aug 20, 2019 10:59 AM, GMT-5
Weather:
min. 74ºF, max. 85ºF

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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