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

The cheapest flights right now

Chicago – San Juan
Outbound – Dec 25, 2025
AAORD
direct
4h 40m
SJU
Return – Jan 3, 2026
AASJU
direct
5h 25m
ORD
$1,221
7 days ago
Chicago – San Juan
Outbound – Dec 25, 2025
AAORD
1 stop
6h 50m
MIA
SJU
Return – Jan 3, 2026
AASJU
direct
5h 25m
ORD
$1,098
7 days ago
Chicago – San Juan
Outbound – Dec 25, 2025
AAORD
direct
4h 40m
SJU
Return – Jan 3, 2026
AASJU
direct
5h 25m
ORD
$1,093
7 days ago

* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.

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 [[timezone]]. In Chicago, it is currently {fromLocalTime}, the temperature is on average 21°C, with a minimum of 20°C and a maximum of 24°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 [[timezone]]. In San Juan, it is currently {toLocalTime}, the temperature is on average 27°C, with a minimum of 26°C and a maximum of 32°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 December. 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?

This information is not available at this time.

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

This information is not available at this time.

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 77 mm in San Juan and 130 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

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