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Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$301

outward: May 7, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)

inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$302

outward: May 7, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)

inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$305

outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)

inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$308

outward: Dec 26, 2019
1:55p ORD » 1:50p SJU
JetBlue 1 stop (23h55m)

inbound: Jan 6, 2020
2:35p SJU » 7:06a ORD
JetBlue 1 stop (16h31m)

$312

outward: May 8, 2019
11:50p ORD » 9:39p SJU
Spirit Airlines 2 stops (21h49m)

inbound: May 16, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)

$316

outward: May 8, 2019
2:10p ORD » 1:06a SJU
Spirit Airlines 1 stop (10h56m)

inbound: May 15, 2019
5:00p SJU » 6:35a ORD
Spirit Airlines 1 stop (13h35m)

$318

outward: Sep 18, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)

inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)

$326

outward: Sep 19, 2019
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)

inbound: Sep 26, 2019
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)

$331

outward: Sep 9, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)

inbound: Sep 13, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$333

outward: Sep 19, 2019
2:49p ORD » 10:48p SJU
Frontier Airlines 1 stop (7h59m)

inbound: Sep 26, 2019
9:30a SJU » 9:47p ORD
Frontier Airlines 1 stop (12h17m)

$335

outward: May 7, 2019
4:42p ORD » 3:13a SJU
Spirit Airlines 2 stops (10h31m)

inbound: May 22, 2019
5:00p SJU » 6:35a ORD
Spirit Airlines 1 stop (13h35m)

$337

outward: May 7, 2019
4:42p ORD » 3:13a SJU
Spirit Airlines 2 stops (10h31m)

inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$343

outward: Sep 18, 2019
9:09p ORD » 8:11a SJU
JetBlue 1 stop (11h02m)

inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)

$343

outward: Sep 18, 2019
9:09p ORD » 8:11a SJU
JetBlue 1 stop (11h02m)

inbound: Sep 23, 2019
10:40p SJU » 6:35p ORD
Spirit Airlines 1 stop (19h55m)

$343

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)

$344

outward: May 9, 2019
11:50p ORD » 8:38a SJU
Spirit Airlines 2 stops (8h48m)

inbound: May 10, 2019
5:00p SJU » 7:27a ORD
Spirit Airlines 1 stop (14h27m)

$344

outward: Apr 24, 2019
11:40p ORD » 8:45a SJU
Spirit Airlines 2 stops (33h05m)

inbound: Apr 30, 2019
1:53a SJU » 6:19a ORD
Spirit Airlines 1 stop (28h26m)

$347

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)

$347

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)

$348

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 12, 2019
2:45a SJU » 7:50p ORD
Spirit Airlines 1 stop (17h05m)

$349

outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)

inbound: May 22, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$352

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$353

outward: May 9, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)

inbound: May 10, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$353

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$354

outward: Jun 3, 2019
12:15p ORD » 7:13p SJU
Spirit Airlines 1 stop (6h58m)

inbound: Jun 11, 2019
10:41p SJU » 7:27a ORD
Spirit Airlines 1 stop (8h46m)

$355

outward: May 8, 2019
1:57p ORD » 8:30a SJU
JetBlue 1 stop (18h33m)

inbound: May 16, 2019
2:32a SJU » 5:48a ORD
JetBlue 1 stop (27h16m)

$356

outward: Sep 30, 2019
4:05p ORD » 9:00p SJU
American Airlines direct (4h55m)

inbound: Oct 7, 2019
8:55p SJU » 1:57a ORD
American Airlines direct (5h02m)

$358

outward: May 8, 2019
11:50p ORD » 8:21p SJU
Unknown Company 1 stop (20h31m)

inbound: May 15, 2019
9:50a SJU » 3:15a ORD
Unknown Company 1 stop (17h25m)

$360

outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)

inbound: May 23, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)

$360

outward: May 7, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)

inbound: May 23, 2019
1:59a SJU » 1:13a ORD
Spirit Airlines 1 stop (23h14m)

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
21 December Dec Saturday $outDate.dayShortName
22 December Dec Sunday $outDate.dayShortName
23 December Dec Monday $outDate.dayShortName	$656			$694	$798
24 December Dec Tuesday $outDate.dayShortName	$694			$755
25 December Dec Wednesday $outDate.dayShortName
26 December Dec Thursday $outDate.dayShortName						$299	$813
27 December Dec Friday $outDate.dayShortName						$745

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: Apr 26, 2019
Spirit Airlines 1 stop

return: Apr 29, 2019
Spirit Airlines 2 stops

JetBlue

outbound: Dec 18, 2019
JetBlue 1 stop

return: Jan 2, 2020
JetBlue 1 stop

Frontier Airlines

outbound: Apr 26, 2019
Frontier Airlines 1 stop

return: Apr 29, 2019
Spirit Airlines 1 stop

American Airlines

outbound: Apr 26, 2019
American Airlines direct

return: Apr 29, 2019
American Airlines 1 stop

United Airlines

outbound: Apr 26, 2019
United Airlines direct

return: Apr 29, 2019
United Airlines 1 stop

Delta Air Lines

outbound: Apr 24, 2019
Delta Air Lines 1 stop

return: Apr 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: 4h58m (direct flight)

Arrival city:
San Juan, Puerto Rico
Airport(s):
Fernando Luis Ribas Dominicci Airport (SIG)
Luis Muñoz Marín International Airport (SJU)
Local time:
Apr 20, 2019 8:20 AM, GMT-4
Weather:
min. 61ºF, max. 72ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Apr 20, 2019 7:20 AM, GMT-5
Weather:
min. 44ºF, max. 60ºF

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