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

Find cheap airline tickets from Chicago to San Juan by date

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$147
Frontier Airlines outward: Feb 21, 2022
3:00a ORD » 7:45a SJU
Frontier Airlines direct (4h45m)
Frontier Airlines inbound: Feb 25, 2022
8:47a SJU » 2:23p ORD
Frontier Airlines direct (5h36m)
$235
Spirit Airlines outward: Feb 18, 2022
1:40p ORD » 5:44a SJU
Spirit Airlines 1 stop (16h04m)
Frontier Airlines inbound: Feb 22, 2022
10:08p SJU » 7:24a ORD
Frontier Airlines 1 stop (9h16m)
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

  • any
  • December 2021
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  • Frontier Airlines
  • Spirit Airlines
Spirit Airlines
outbound: Feb 20, 2022
Spirit Airlines 1 stop
return: Feb 25, 2022
Spirit Airlines 1 stop
Frontier Airlines
outbound: Feb 20, 2022
Frontier Airlines direct
return: Feb 25, 2022
Frontier Airlines direct

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 5h10m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Dec 8, 2021 2:36 PM, GMT-4
  • Weather:
  • min. 61ºF, max. 72ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 8, 2021 12:36 PM, GMT-6
  • Weather:
  • min. 29ºF, max. 39ºF

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!