Cheap flights from Puerto Rico to Chicago from $76
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Puerto Rico to Chicago departing on 10/12. 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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United Airlines flights from Puerto Rico to Chicago
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Spirit Airlines flights from Puerto Rico to Chicago
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How to get the cheapest flight ticket from Puerto Rico to Chicago
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 Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $232. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $270.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $341. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Puerto Rico to Chicago for around $482.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Puerto Rico to Chicago during this time can be as low as $243. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $480.
What is the cheapest Puerto Rico to Chicago flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Puerto Rico - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Puerto Rico for as low as $244 on momondo.
What cabin class options are available on Puerto Rico to Chicago flights?
There are 4 cabin classes available to choose from on Puerto Rico to Chicago 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 Puerto Rico to Chicago?
Frontier and Spirit Airlines are the most popular carriers operating from Puerto Rico to Chicago
What airlines fly to Chicago?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Puerto Rico according to our data. Spirit Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Puerto Rico to Chicago on average per day?
The number of flights available between Puerto Rico and Chicago is 9 per day as of June 2025. The most frequent departure time is 3:00PM, with 55% of daily flights leaving in the afternoon.
How many flights depart from Puerto Rico to Chicago on average per week?
63 flights are operational weekly from Puerto Rico to Chicago as of June 2025. The most popular departure day for this route is Sat, with 16% of flights per week taking off on this day.
Cheap Puerto Rico to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago
When did momondo last update prices for flights from Puerto Rico to Chicago?
Prices for flights from Puerto Rico to Chicago were last updated today.
How many operators does momondo search for flights from Puerto Rico to Chicago?
As of June 2025, there are 6 operators available to choose from for flights from Puerto Rico to Chicago.
How old do you have to be to fly from Puerto Rico to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Puerto Rico to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Puerto Rico to Chicago?
Based on momondo bookings for flights between Puerto Rico and Chicago, the leading plane model is Airbus A321neo, making up 31.03% of the total bookings. Other popular models include Boeing 737 MAX 9 with 28.60%, Airbus A320neo with 16.75%, and Boeing 737-900 with 6.94%.
Best airlines flying from Puerto Rico to Chicago
Compare and see reviews for airlines that fly from Puerto Rico to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $130 | Free Cancellation | Rating 5.9 3,293 reviews | |||
| PriceFrom $136 | Free Cancellation | Rating 6.3 8,096 reviews | |||
| PriceFrom $160 | Free Cancellation | Rating 7.4 8,852 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 8.0 7,969 reviews | |||
| PriceFrom $257 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $329 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Puerto Rico to Chicago?
It is quick and easy to find Puerto Rico to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Puerto Rico to Chicago with flexible booking policies on momondo?
Flights from Puerto Rico to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Puerto Rico to Chicago?
Once you have performed a search for Puerto Rico to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Puerto Rico to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Puerto Rico 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.