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Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$240

outward: Jan 29, 2020
2:00p ORD » 6:20a SJU
Spirit Airlines 1 stop (16h20m)

inbound: Feb 8, 2020
11:30a SJU » 4:39a ORD
Spirit Airlines 1 stop (17h09m)

$251

outward: Jan 29, 2020
2:00p ORD » 6:20a SJU
Spirit Airlines 1 stop (16h20m)

inbound: Feb 8, 2020
10:28p SJU » 7:05a ORD
Spirit Airlines 1 stop (8h37m)

$279

outward: Dec 5, 2019
11:24p ORD » 3:40p SJU
Spirit Airlines 1 stop (16h16m)

inbound: Dec 13, 2019
2:45a SJU » 10:09p ORD
Spirit Airlines 1 stop (19h24m)

$285

outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)

inbound: Feb 8, 2020
3:20p SJU » 4:39a ORD
Spirit Airlines 1 stop (13h19m)

$286

outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)

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

$290

outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)

inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)

$291

outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)

inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)

$292

outward: Jan 29, 2020
6:12p ORD » 1:21a SJU
Spirit Airlines 1 stop (7h09m)

inbound: Feb 9, 2020
12:21a SJU » 4:00p ORD
Unknown Company 1 stop (15h39m)

$298

outward: Dec 10, 2019
1:20a ORD » 4:31p SJU
Spirit Airlines 1 stop (15h11m)

inbound: Dec 17, 2019
8:03p SJU » 5:15a ORD
Spirit Airlines 1 stop (9h12m)

$302

outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)

inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)

$312

outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)

inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)

$312

outward: Feb 1, 2020
11:45p ORD » 3:23p SJU
Spirit Airlines 1 stop (15h38m)

inbound: Feb 10, 2020
2:15a SJU » 3:05p ORD
Spirit Airlines 1 stop (12h50m)

$325

outward: Dec 6, 2019
11:24p ORD » 3:40p SJU
Spirit Airlines 1 stop (16h16m)

inbound: Dec 19, 2019
8:35p SJU » 1:46a ORD
United Airlines direct (5h11m)

$341

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 8, 2020
11:05a SJU » 4:12p ORD
United Airlines direct (5h07m)

$341

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 8, 2020
11:05a SJU » 4:12p ORD
United Airlines direct (5h07m)

$342

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 8, 2020
6:45a SJU » 11:46a ORD
United Airlines direct (5h01m)

$376

outward: Apr 25, 2020
10:30p ORD » 3:25a SJU
American Airlines direct (4h55m)

inbound: Apr 29, 2020
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)

$379

outward: Apr 25, 2020
10:30p ORD » 3:25a SJU
American Airlines direct (4h55m)

inbound: Apr 29, 2020
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)

$409

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 8, 2020
7:01a SJU » 4:30p ORD
United Airlines 1 stop (9h29m)

$410

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 8, 2020
7:01a SJU » 4:30p ORD
United Airlines 1 stop (9h29m)

$415

outward: Dec 2, 2019
5:29p ORD » 7:59a SJU
Frontier Airlines 1 stop (14h30m)

inbound: Dec 17, 2019
8:55a SJU » 3:03a ORD
Frontier Airlines 1 stop (18h08m)

$415

outward: Dec 2, 2019
5:29p ORD » 7:59a SJU
Frontier Airlines 1 stop (14h30m)

inbound: Dec 17, 2019
8:55a SJU » 3:03a ORD
Frontier Airlines 1 stop (18h08m)

$436

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 9, 2020
1:05a SJU » 6:49a ORD
JetBlue 1 stop (29h44m)

$436

outward: Mar 5, 2020
2:50p ORD » 9:58p SJU
Frontier Airlines 1 stop (7h08m)

inbound: Mar 9, 2020
1:05a SJU » 6:49a ORD
JetBlue 1 stop (29h44m)

$453

outward: Mar 5, 2020
2:50p ORD » 7:55a SJU
Frontier Airlines 1 stop (17h05m)

inbound: Mar 8, 2020
7:55a SJU » 2:03a ORD
Frontier Airlines 1 stop (18h08m)

$466

outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)

inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)

$466

outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)

inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)

$466

outward: Dec 23, 2019
1:45p ORD » 7:13p SJU
JetBlue 2 stops (29h28m)

inbound: Jan 4, 2020
7:16a SJU » 4:00p ORD
JetBlue 1 stop (8h44m)

$479

outward: Nov 24, 2019
3:45a ORD » 6:57p SJU
Spirit Airlines 1 stop (15h12m)

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

$494

outward: Dec 26, 2019
2:50p ORD » 9:58p SJU
Frontier Airlines direct (7h08m)

inbound: Jan 10, 2020
4:59a SJU » 5:00p ORD
Spirit Airlines 1 stop (12h01m)

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
18 December Dec Wednesday $outDate.dayShortName				$566	$662	$511
19 December Dec Thursday $outDate.dayShortName			$558	$558		$549
20 December Dec Friday $outDate.dayShortName			$620
21 December Dec Saturday $outDate.dayShortName						$610
22 December Dec Sunday $outDate.dayShortName						$720
23 December Dec Monday $outDate.dayShortName	$591	$625		$447	$614		$560
24 December Dec Tuesday $outDate.dayShortName	$581			$801	$727		$568

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: Dec 18, 2019
JetBlue 1 stop

return: Dec 23, 2019
Spirit Airlines 1 stop

Spirit Airlines

outbound: Nov 22, 2019
Spirit Airlines 1 stop

return: Dec 1, 2019
Spirit Airlines 2 stops

Frontier Airlines

outbound: Nov 22, 2019
Frontier Airlines 1 stop

return: Dec 1, 2019
Air Canada 1 stop

United Airlines

outbound: Nov 22, 2019
United Airlines 1 stop

return: Dec 1, 2019
United 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: 7h13m (direct flight)

Arrival city:
San Juan, Puerto Rico
Airport(s):
Fernando Luis Ribas Dominicci Airport (SIG)
Luis Muñoz Marín International Airport (SJU)
Local time:
Oct 23, 2019 9:42 PM, GMT-4
Weather:
min. 59ºF, max. 83ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Oct 23, 2019 8:42 PM, GMT-5
Weather:
min. 42ºF, 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!

Find a cheap rental car in San Juan