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Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$135

outward: Mar 3, 2020
12:15p ORD » 7:19p SJU
Spirit Airlines 1 stop (7h04m)

inbound: Mar 11, 2020
9:28p SJU » 4:22a ORD
Spirit Airlines 1 stop (6h54m)

$146

outward: Mar 3, 2020
12:15p ORD » 7:19p SJU
Spirit Airlines 1 stop (7h04m)

inbound: Mar 11, 2020
7:15p SJU » 5:52a ORD
Spirit Airlines 1 stop (10h37m)

$169

outward: Mar 3, 2020
2:00p ORD » 6:52a SJU
Spirit Airlines 1 stop (16h52m)

inbound: Mar 11, 2020
7:15p SJU » 5:52a ORD
Spirit Airlines 1 stop (10h37m)

$177

outward: Feb 10, 2020
2:00p ORD » 6:50a SJU
Spirit Airlines 1 stop (16h50m)

inbound: Feb 28, 2020
6:51p SJU » 6:21a ORD
Spirit Airlines 1 stop (11h30m)

$198

outward: Feb 10, 2020
6:00p ORD » 5:27a SJU
Spirit Airlines 1 stop (11h27m)

inbound: Feb 28, 2020
11:00a SJU » 5:25p ORD
Spirit Airlines 1 stop (30h25m)

$203

outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)

inbound: Feb 9, 2020
2:45a SJU » 10:16p ORD
Spirit Airlines 2 stops (19h31m)

$227

outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)

inbound: Feb 8, 2020
3:35p SJU » 4:44a ORD
Spirit Airlines 1 stop (13h09m)

$255

outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)

inbound: Jun 25, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)

$262

outward: Jan 29, 2020
4:00p ORD » 1:15a SJU
Spirit Airlines 1 stop (9h15m)

inbound: Feb 8, 2020
6:30a SJU » 5:28p ORD
Spirit Airlines 1 stop (10h58m)

$287

outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)

inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)

$287

outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)

inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)

$290

outward: Jun 18, 2020
2:07p ORD » 7:04p SJU
Frontier Airlines direct (4h57m)

inbound: Jul 2, 2020
8:04p SJU » 1:33a ORD
Frontier Airlines direct (5h29m)

$306

outward: Mar 5, 2020
3:01p ORD » 10:13p SJU
Frontier Airlines 1 stop (7h12m)

inbound: Mar 8, 2020
11:00a SJU » 4:10p ORD
Unknown Company 1 stop (29h10m)

$308

outward: Mar 5, 2020
3:01p ORD » 8:00a SJU
Frontier Airlines 1 stop (16h59m)

inbound: Mar 8, 2020
10:13p SJU » 2:07p ORD
Unknown Company 1 stop (15h54m)

$331

outward: Mar 5, 2020
2:17p ORD » 8:24a SJU
JetBlue 1 stop (18h07m)

inbound: Mar 9, 2020
4:45a SJU » 6:49a ORD
JetBlue 1 stop (26h04m)

$332

outward: Apr 9, 2020
2:30p ORD » 2:35a SJU
JetBlue 1 stop (12h05m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$337

outward: Aug 17, 2020
12:09p ORD » 6:27p SJU
JetBlue 1 stop (6h18m)

inbound: Aug 22, 2020
5:59a SJU » 4:13p ORD
Spirit Airlines 1 stop (10h14m)

$347

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$348

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$351

outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)

inbound: Apr 13, 2020
2:15p SJU » 7:49a ORD
JetBlue 1 stop (17h34m)

$353

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)

$353

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)

$353

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)

$353

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)

$358

outward: Apr 9, 2020
2:30p ORD » 1:47p SJU
JetBlue 1 stop (23h17m)

inbound: Apr 13, 2020
2:32p SJU » 7:49a ORD
JetBlue 1 stop (17h17m)

$364

outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$365

outward: Apr 9, 2020
2:30p ORD » 1:24p SJU
JetBlue 1 stop (22h54m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$365

outward: Apr 9, 2020
2:30p ORD » 2:12a SJU
JetBlue 1 stop (11h42m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$370

outward: Apr 9, 2020
2:30p ORD » 2:12a SJU
JetBlue 1 stop (11h42m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

$371

outward: Apr 9, 2020
2:30p ORD » 12:57a SJU
JetBlue 1 stop (10h27m)

inbound: Apr 14, 2020
5:45a SJU » 7:49a ORD
JetBlue 1 stop (26h04m)

Return

Departure

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: Aug 17, 2020
JetBlue 1 stop

return: Aug 21, 2020
Spirit Airlines 1 stop

American Airlines

outbound: Aug 17, 2020
American Airlines 1 stop

return: Aug 21, 2020
Spirit Airlines 1 stop

Frontier Airlines

outbound: Aug 17, 2020
Frontier Airlines direct

return: Aug 21, 2020
American Airlines 1 stop

United Airlines

outbound: Aug 17, 2020
United Airlines direct

return: Aug 21, 2020
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: 12h47m (flight with stopovers)

Arrival city:
San Juan, Puerto Rico
Airport(s):
Fernando Luis Ribas Dominicci Airport (SIG)
Luis Muñoz Marín International Airport (SJU)
Local time:
Jan 25, 2020 6:43 PM, GMT-4
Weather:
min. 83ºF, max. 97ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Jan 25, 2020 4:43 PM, GMT-6
Weather:
min. 31ºF, max. 34ºF

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