Cheap flights from Chicago to San Juan

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Looking for the price of a flight from Chicago to San Juan?

There’s no fixed price — fares between Chicago and San Juan can vary a lot by day or time.

Select your dates to check current offers.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

Flying from or to Chicago and San Juan? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

  • Airports in Chicago: You have 3 departure options - Midway, O'Hare, Rockford.
  • Airports in San Juan: Isla Grande is a secondary arrival airport.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Flights from Chicago to San Juan - Luis Muñoz Marín

Explore flights from Chicago to San Juan your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by specific travel agency.

Other popular destinations

Also interested in Puerto Rico? Check out: Aguadilla, Culebra Airport, Mayaguez, Ponce, San Juan.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to San Juan.

How much does an airline ticket from Chicago to San Juan cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to San Juan.

How far is Chicago from San Juan?

Chicago is about 3314 km from San Juan.

What are the airports in San Juan?

San Juan has another airport: Isla Grande.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Puerto Rico?

The most popular cities in Puerto Rico according to our users' searches are: Aguadilla, Culebra Airport, Mayaguez, Ponce, San Juan.

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

This information is not available at the moment.

What is the cheapest month to fly from Chicago to San Juan?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to San Juan?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to San Juan?

This information is not available at the moment.