Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to San Juan
The cheapest flights right now
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
13h 10m FLL
Return – Nov 21, 2026
direct
5h 9m $303
2 days ago
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
12h 29m SFB
Return – Nov 21, 2026
direct
5h 9m $311
2 days ago
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
7h 37m PUJ
Return – Nov 21, 2026
direct
5h 9m $432
2 days ago
Chicago – San Juan
Outbound – Feb 13, 2027
direct
4h 46m Return – Feb 23, 2027
direct
5h 28m $502
3 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.
Cheapest flight tickets
$198
Average price of a round trip
$220
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
4h57
A flight from Chicago to San Juan takes on average 4h57.
Best time
October
According to user searches, the ideal month to go to San Juan is October.
What is the cheapest month for this flight?
Monthly price data (Table View)
October
Oct
$234
November
Nov
$0
December
Dec
$510
January
Jan
$0
February
Feb
$350
March
Mar
$0
April
Apr
$571
May
May
June
Jun
July
Jul
$365
August
Aug
$291
September
Sep
$170
* The prices shown are an average per month of the prices found by Liligo users during the last 30 days.
The best flight deals for a week
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
13h 10m FLL
Return – Nov 21, 2026
direct
5h 9m $303
2 days ago
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
12h 29m SFB
Return – Nov 21, 2026
direct
5h 9m $311
2 days ago
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
7h 37m PUJ
Return – Nov 21, 2026
direct
5h 9m $432
2 days ago
Chicago – San Juan
Outbound – Nov 13, 2026
1 stop
16h 13m PHL
Return – Nov 21, 2026
direct
5h 9m $245
2 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.
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 February, with an average flight ticket price of $101 (calculation over the last two years). The most touristic season corresponds to the months of May, December and October.
For the cheapest flights, it is advisable to buy your ticket at least 24 days before the departure date.
The airline offering the cheapest flight tickets is Frontier Airlines. A ticket from the airline Frontier Airlines to San Juan costs on average $215.
The airlines that offer the most flights are United Airlines and United 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 $198 to $476
- The average price of a flight ticket is about $220
- Prices are lowest for stays in the month of February
- The month in which booking a ticket is cheaper is: October
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 14°C, with a minimum of 10°C and a maximum of 20°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 30°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 October.
What is the most popular time to travel to San Juan?
In San Juan, the most popular month is May. 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 24 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. You can also choose morning flights that are 100% cheaper than afternoon and evening flights. 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-Midway or 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 79 mm in San Juan and 145 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.
