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

  • any
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • September 2024
  • October 2024
  • November 2024
  • December 2024
  • January 2025
  • any
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • September 2024
  • October 2024
  • November 2024
  • December 2024
  • January 2025
  • price
  • month of departure
  • month of return
$215
Unknown Company outward: Apr 25, 2024
5:07p ORD » 2:34p SJU
Unknown Company 1 stop (21h27m)
Unknown Company inbound: Apr 29, 2024
3:34p SJU » 3:28p ORD
Unknown Company 1 stop (23h54m)
$233
Spirit Airlines outward: Apr 25, 2024
6:20p ORD » 11:03p SJU
Spirit Airlines direct (4h43m)
Spirit Airlines inbound: Apr 29, 2024
12:00p SJU » 5:19p ORD
Spirit Airlines direct (5h19m)
$233
Spirit Airlines outward: Apr 25, 2024
6:20p ORD » 11:03p SJU
Spirit Airlines direct (4h43m)
Spirit Airlines inbound: Apr 29, 2024
12:00p SJU » 5:19p ORD
Spirit Airlines direct (5h19m)
$307
Spirit Airlines outward: Apr 25, 2024
2:30p ORD » 7:15p SJU
Spirit Airlines direct (4h45m)
Spirit Airlines inbound: Apr 29, 2024
8:11p SJU » 1:20a ORD
Spirit Airlines direct (5h09m)
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
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • September 2024
  • October 2024
  • November 2024
  • December 2024
  • January 2025
  • all
  • Delta Air Lines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Apr 25, 2024
Spirit Airlines 1 stop
return: Apr 29, 2024
Frontier Airlines 1 stop
Frontier Airlines
outbound: Apr 25, 2024
Frontier Airlines 1 stop
return: Apr 29, 2024
Frontier Airlines 1 stop
United Airlines
outbound: Apr 25, 2024
United Airlines direct
return: Apr 29, 2024
Delta Air Lines 1 stop
Delta Air Lines
outbound: Apr 25, 2024
Delta Air Lines 1 stop
return: Apr 29, 2024
Delta Air Lines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 4h57m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Feb 24, 2024 5:01 AM, GMT-4
  • Weather:
  • min. 70ºF, max. 90ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Feb 24, 2024 3:01 AM, GMT-6
  • Weather:
  • min. 31ºF, max. 44ºF

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!