Take off on cheap flights from Chicago to San Juan, your adventure starts now!

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$363
Unknown Company outward: Oct 7, 2022
1:30p ORD » 1:03a SJU
Unknown Company 1 stop (11h33m)
Unknown Company inbound: Oct 11, 2022
3:26p SJU » 3:31a ORD
Unknown Company 1 stop (12h05m)
$363
Unknown Company outward: Oct 7, 2022
1:30p ORD » 1:03a SJU
Unknown Company 1 stop (11h33m)
Unknown Company inbound: Oct 11, 2022
3:26p SJU » 3:31a ORD
Unknown Company 1 stop (12h05m)
$383
American Airlines outward: Oct 7, 2022
11:40p ORD » 3:25p SJU
American Airlines 1 stop (15h45m)
JetBlue inbound: Oct 13, 2022
3:05p SJU » 10:38p ORD
JetBlue 1 stop (7h33m)
$403
American Airlines outward: Oct 7, 2022
11:40p ORD » 3:25p SJU
American Airlines 1 stop (15h45m)
American Airlines inbound: Oct 13, 2022
11:23p SJU » 6:47a ORD
American Airlines 1 stop (7h24m)
$467
Spirit Airlines outward: Jul 6, 2022
12:05p ORD » 10:04p SJU
Spirit Airlines 1 stop (9h59m)
Frontier Airlines inbound: Jul 10, 2022
3:41p SJU » 5:15p MDW
Frontier Airlines 1 stop (25h34m)
$469
Unknown Company outward: Jul 28, 2022
2:41a ORD » 2:51p SJU
Unknown Company 1 stop (12h10m)
Frontier Airlines inbound: Jul 31, 2022
1:30p SJU » 3:34p ORD
Frontier Airlines 1 stop (26h04m)
Return
Departure
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

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  • June 2022
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  • Frontier Airlines
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Spirit Airlines
outbound: Oct 7, 2022
Spirit Airlines 1 stop
return: Oct 11, 2022
Spirit Airlines 1 stop
United Airlines
outbound: Oct 7, 2022
United Airlines 1 stop
return: Oct 11, 2022
United Airlines 1 stop
Frontier Airlines
outbound: Oct 7, 2022
Frontier Airlines 1 stop
return: Oct 11, 2022
Frontier Airlines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 11h41m (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:
  • Jun 27, 2022 4:26 PM, GMT-4
  • Weather:
  • min. 37ºF, max. 63ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 27, 2022 3:26 PM, GMT-5
  • Weather:
  • min. 60ºF, max. 76ºF

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!