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 8/11. 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
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Spirit Airlines flights from Chicago to San Juan
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How to get the cheapest flight ticket from Chicago to San Juan
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?
What is the cheapest month to fly to San Juan?
If you’re not able to fly to San Juan in September, then August is your next best option. Flight prices from Chicago to San Juan during August average around $321.
What is the cheapest day to depart on your flight to San Juan?
The cheapest day to depart from Chicago to San Juan is on a Monday when prices can be found for as low as $391. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $448.
What is the cheapest time of day to depart on your flight to San Juan?
The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $300. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $438 on average. Flights to San Juan from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago to San Juan flight route?
Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices
How far in advance should I book a flight to San Juan?
You are more likely to see cheaper flights to San Juan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan 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 from Chicago for as low as $301 on momondo.
What cabin class options are available on Chicago to San Juan flights?
There are 4 cabin classes available to choose from on Chicago to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to San Juan?
Frontier and Spirit Airlines are the most popular carriers operating from Chicago to San Juan
What airlines fly to San Juan?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to San Juan 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. Keep in mind that there are 7 different airlines that fly to San Juan on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to San Juan on average per day?
9 flights are operational daily from Chicago to San Juan as of June 2025. The most popular departure time for this route is 8:00AM, with 55% of flights per day taking off at noon.
How many flights depart from Chicago to San Juan on average per week?
As of June 2025, there are 63 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Sat, with 16% of flights taking off on this day.
Cheap Chicago to San Juan flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan
How far is Chicago to San Juan by plane?
San Juan is 2052.1 mi away from Chicago. 4h 43m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to San Juan?
Prices for flights from Chicago to San Juan refresh daily.
How many operators does momondo search for flights from Chicago to San Juan?
As of June 2025, there are 7 operators available to choose from for flights from Chicago to San Juan.
How old do you have to be to fly from Chicago to San Juan?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan.
What documentation or ID do you need to fly to San Juan?
The travel and health documents required for your trip to San Juan 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. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
Best airlines flying from Chicago to San Juan
Compare and see reviews for airlines that fly from Chicago to San Juan with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $106 | Free Cancellation | Rating 5.9 3,293 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 6.3 8,096 reviews | |||
| PriceFrom $212 | Free Cancellation | Rating 8.0 7,969 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 7.4 8,852 reviews | |||
| PriceFrom $287 | Free Cancellation | Rating 7.3 2,920 reviews | |||
| PriceFrom $338 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $354 | Free Cancellation | Rating 8.0 4,278 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to San Juan?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Juan from Chicago.
Can I find flights from Chicago to San Juan with flexible booking policies on momondo?
Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
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?
Yes momondo offers price alerts on flights to San Juan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.