Compare all flight tickets and find cheap flights from Chicago to San Juan

Cheapest flight tickets


Price observed over the last 3 months for a round trip.

Average price of a round trip


Average flight ticket price recorded over the last 3 months for a round trip.

Flight duration


A flight from Chicago to San Juan takes on average 4h43.

Best time


According to user searches, the ideal month to go to San Juan is May.

Tips for finding a cheap flight from Chicago to San Juan

Check out our tips for booking your flight to San Juan (Puerto Rico) from Chicago (USA) at the cheapest possible price.

Usually, the cheapest month to pick up a ticket on this route is July, with an average flight ticket price of $357 (calculation over the last two years). The most touristic season corresponds to the months of July.
For the cheapest flights, it is advisable to buy your ticket at least 19 days before the departure date.

The airline offering the cheapest flight tickets is Spirit Airlines. A ticket from the airline Spirit Airlines to San Juan costs on average $272.
The airlines that offer the most flights are Spirit Airlines and Spirit Airlines.

Price of flight tickets from Chicago to San Juan

Here is some information and tips to know before booking your flight:

  • Flight ticket prices range from $231 to $514
  • The average price of a flight ticket is about $272
  • Prices are lowest for stays in the month of July
  • The month in which booking a ticket is cheaper is: July
info departure city :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :

Chicago is a city in the country USA, the time zone is GMT . In Chicago, it is currently {fromLocalTime}, the temperature is on average 14°C, with a minimum of 12°C and a maximum of 17°C.

The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare

destination info :
San Juan, Puerto Rico
airports :
Luis Muñoz Marín International Airport (SJU)
Fernando Luis Ribas Dominicci Airport (SIG)
local time :

San Juan is in the country Puerto Rico, the time zone is GMT . In San Juan, it is currently {toLocalTime}, the temperature is on average 28°C, with a minimum of 26°C and a maximum of 31°C.

The city of San Juan has 2 airport(s): Luis Muñoz Marín and Fernando Luis Ribas Dominicci

Useful info about San Juan

What is the least touristic period to go to San Juan?

If you want to visit San Juan during the least touristic period, choose the month of May.

What is the most popular time to travel to San Juan?

In San Juan, the most popular month is July. It is during this period that the prices offered by airlines are also the highest.

When should I book my flight from Chicago to San Juan?

According to our data, it is recommended to book your flight 19 days before your departure. If you book your flight ticket 3 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Chicago to San Juan is Monday.

What are the arrival and destination airports when traveling between Chicago and San Juan?

When you leave, you can leave from Chicago-O'Hare, and you will arrive at Luis Muñoz Marín.

How to reach Chicago airport from the city centre?

The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.

Are there other means of transportation to go from Chicago to San Juan?

Airplane is the only means of transportation listed on Liligo for this journey.

Are there big differences in weather between Chicago and San Juan?

In summer, the average temperature is 28°C in San Juan and 22°C in Chicago. The average rainfall in summer is 76 mm in San Juan and 131 mm in Chicago. In summer, it is warmer in San Juan and it rains less in San Juan. In winter, it is colder in San Juan and it rains more in Chicago.

Prepare your stay in San Juan

Discover other cheap flight deals