Cheap flights from Chicago to San Juan from $65
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from Chicago to San Juan Luis Munoz Marin Intl Airport
Our best Frontier deals on Chicago to San Juan Luis Munoz Marin Intl Airport flight tickets
Spirit Airlines flights from Chicago to San Juan Luis Munoz Marin Intl Airport
Our best Spirit Airlines deals on Chicago to San Juan Luis Munoz Marin Intl Airport flight tickets
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How to get the cheapest flight ticket from Chicago to San Juan Luis Munoz Marin Intl Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and San Juan Luis Munoz Marin Intl Airport?
What is the cheapest month to fly to San Juan Luis Munoz Marin Intl Airport?
If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $321.
What is the cheapest day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?
On average, the least expensive day to fly to San Juan Luis Munoz Marin Intl Airport from Chicago is on a Monday. momondo users have found tickets for Monday departures for as low as $391. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $448.
What is the cheapest time of day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?
The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $300. Flights in the morning are often more expensive with an average ticket price of $438.
What is the cheapest Chicago to San Juan Luis Munoz Marin Intl flight route?
Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan Luis Munoz Marin Intl flight prices
How far in advance should I book a flight to San Juan Luis Munoz Marin Intl Airport?
You are more likely to see cheaper flights to San Juan Luis Munoz Marin Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan Luis Munoz Marin Intl Airport for around $373 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan Luis Munoz Marin Intl Airport from Chicago for as low as $301 on momondo.
What cabin class options are available on Chicago to San Juan Luis Munoz Marin Intl flights?
There are 4 cabin classes available to choose from on Chicago to San Juan Luis Munoz Marin Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to San Juan Luis Munoz Marin Intl Airport flights?
No. A direct flight is the cheapest option for a flight between Chicago to San Juan Luis Munoz Marin Intl Airport.
How have Chicago to San Juan Luis Munoz Marin Intl Airport flight prices changed over time?
As of July 2025, prices for Chicago to San Juan Luis Munoz Marin Intl Airport flights are approximately 5% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to San Juan Luis Munoz Marin Intl?
Frontier and Spirit Airlines are the most popular carriers operating from Chicago to San Juan Luis Munoz Marin Intl
What airlines fly to San Juan Luis Munoz Marin Intl Airport?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to San Juan Luis Munoz Marin Intl Airport from Chicago according to our data. Spirit Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to San Juan Luis Munoz Marin Intl Airport. Keep in mind that there are 7 different airlines that fly to San Juan Luis Munoz Marin Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to San Juan Luis Munoz Marin Intl Airport on average per day?
The number of flights available between Chicago and San Juan Luis Munoz Marin Intl Airport is 7 per day as of July 2025. The most frequent departure time is 8:00AM, with 55% of daily flights leaving at noon.
How many flights depart from Chicago to San Juan Luis Munoz Marin Intl Airport on average per week?
53 flights are operational weekly from Chicago to San Juan Luis Munoz Marin Intl Airport as of July 2025. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.
When to book flights from Chicago to San Juan Luis Munoz Marin Intl Airport
Cheap Chicago to San Juan Luis Munoz Marin Intl Airport (CHI to SJU) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan Luis Munoz Marin Intl Airport
How far is Chicago to San Juan Luis Munoz Marin Intl by plane?
There are 2057.4 mi between Chicago and San Juan Luis Munoz Marin Intl. Typically, this will take 4h 39m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to San Juan Luis Munoz Marin Intl Airport?
Prices for flights from Chicago to San Juan Luis Munoz Marin Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to San Juan Luis Munoz Marin Intl Airport?
As of July 2025, there are 7 operators available to choose from for flights from Chicago to San Juan Luis Munoz Marin Intl Airport.
How old do you have to be to fly from Chicago to San Juan Luis Munoz Marin Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan Luis Munoz Marin Intl Airport.
What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?
The travel and health documents required for your trip to San Juan Luis Munoz Marin Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan Luis Munoz Marin Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to San Juan Luis Munoz Marin Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San Juan Luis Munoz Marin Intl Airport is Airbus A321neo (26.95% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (23.58%), Boeing 737-800 (19.38%), and Airbus A320neo (15.43%).
What is the most popular airline from Chicago to San Juan Luis Munoz Marin Intl Airport?
Based on momondo bookings for flights between Chicago and San Juan Luis Munoz Marin Intl Airport, the leading airline is Spirit Airlines, making up 46% of the total bookings. Other popular airlines include United Airlines with 25%, American Airlines with 18%, and Frontier with 5%.
Best airlines flying from Chicago to San Juan Luis Munoz Marin Intl Airport
Compare and see reviews for airlines that fly from Chicago to San Juan Luis Munoz Marin Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $106 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 6.3 8,094 reviews | |||
| PriceFrom $212 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $287 | Free Cancellation | Rating 7.3 2,916 reviews | |||
| PriceFrom $338 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $354 | Free Cancellation | Rating 8.0 4,270 reviews |
United Airlines Flights From Chicago to San Juan Luis Munoz Marin Intl Airport
United Airlines flight deals from Chicago to San Juan Luis Munoz Marin Intl Airport start from $267 round-trip. Over the 14 United Airlines flights for this route in a normal week, average airfare is usually $484 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago to San Juan Luis Munoz Marin Intl Airport
Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to San Juan Luis Munoz Marin Intl Airport about 1 time each week, with ticket deals ranging from $338 to $512. Price data is based on momondo searches in the last 72 hours.
Traveling to a place near San Juan?
Book flights to San Juan if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to San Juan?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Juan. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to San Juan with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to San Juan from Chicago with this policy.
How can momondo help me find flights from Chicago to San Juan?
momondo provides multiple filters to help you find the best flight to San Juan from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?
Price alerts on flights to San Juan from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.