Cheap flights from Chicago to Puerto Rico 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 Puerto Rico departing on 3/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Deals available from 900+ travel sites.
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Puerto Rico
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
JetBlue flights from Chicago to Puerto Rico
Our best JetBlue deals on Chicago to Puerto Rico flight tickets
Delta flights from Chicago to Puerto Rico
Our best Delta deals on Chicago to Puerto Rico flight tickets
See travel insights to Puerto Rico from
How to get the cheapest flight ticket from Chicago to Puerto Rico
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 cheapest month to fly to Puerto Rico?
If you don’t want to visit Puerto Rico in April, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of $297.
What is the cheapest day to depart on your flight to Puerto Rico?
On average, the least expensive day to fly to Puerto Rico from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $363. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Sunday, with ticket prices averaging around $434.
What is the cheapest time of day to depart on your flight to Puerto Rico?
Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago to Puerto Rico during this time can be as low as $326. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $413.
What is the cheapest Chicago to Puerto Rico flight route?
Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - Puerto Rico flight prices
How far in advance should I book a flight to Puerto Rico?
You are more likely to see cheaper flights to Puerto Rico from Chicago when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $363 when searching 7 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago for as low as $298 on momondo.
What cabin class options are available on Chicago to Puerto Rico flights?
There are 4 cabin classes available to choose from on Chicago to Puerto Rico 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 Puerto Rico?
Spirit Airlines, United Airlines, and JetBlue are the most popular carriers operating from Chicago to Puerto Rico
What airlines fly to Puerto Rico?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Puerto Rico from Chicago according to our data. Spirit Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 7 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Puerto Rico on average per day?
4 flights are operational daily from Chicago to Puerto Rico as of February 2025. The most popular departure time for this route is 9:00AM, with 73% of flights per day taking off at noon.
How many flights depart from Chicago to Puerto Rico on average per week?
As of February 2025, there are 33 flights per week flying from Chicago to Puerto Rico. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.
Cheap Chicago to Puerto Rico flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Puerto Rico
When did momondo last update prices for flights from Chicago to Puerto Rico?
Prices for flights from Chicago to Puerto Rico refresh daily.
How many operators does momondo search for flights from Chicago to Puerto Rico?
As of February 2025, there are 7 operators available to choose from for flights from Chicago to Puerto Rico.
How old do you have to be to fly from Chicago to Puerto Rico?
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 Puerto Rico.
What documentation or ID do you need to fly to Puerto Rico?
The travel and health documents required for your trip to Puerto Rico 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 Puerto Rico. 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 Puerto Rico?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Puerto Rico is Boeing 737 MAX 9, representing 27.25% of all bookings. The subsequent popular models are Airbus A320neo at 23.10%, Boeing 737-900 at 16.94%, and Boeing 737-800 at 16.93%.
Best airlines flying from Chicago to Puerto Rico
Compare and see reviews for airlines that fly from Chicago to Puerto Rico with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $124 | Free Cancellation | Rating 6.0 3,339 reviews | |||
| PriceFrom $150 | Free Cancellation | Rating 6.3 7,980 reviews | |||
| PriceFrom $257 | Free Cancellation | Rating 7.4 8,723 reviews | |||
| PriceFrom $262 | Free Cancellation | Rating 8.0 8,140 reviews | |||
| PriceFrom $293 | Free Cancellation | Rating 7.4 3,035 reviews | |||
| PriceFrom $323 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $337 | Free Cancellation | Rating 8.1 4,362 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Puerto Rico?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Puerto Rico for you.
Can I find flights from Chicago to Puerto Rico with flexible booking policies on momondo?
momondo does allow users to show only those flights to Puerto Rico from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Puerto Rico?
momondo helps you find the best flight between Chicago and Puerto Rico by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Puerto Rico right now. Can momondo alert me if prices change?
Price alerts on flights to Puerto Rico 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.