Cheap flights from Puerto Rico to Chicago from $59
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 5/30. 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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1 adult
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0 bags
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Recent round-trip flight deals from Puerto Rico to Chicago
These are some of the best round-trip flight deals from Puerto Rico to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
Recent one-way flight deals from Puerto Rico to Chicago
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Puerto Rico to Chicago.
Recent last minute flight deals from Puerto Rico to Chicago
Planning a quick getaway from Puerto Rico to Chicago? These are the last-minute flight deals available now.
Recent direct flight deals from Puerto Rico to Chicago
If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.
Spirit Airlines flights from Puerto Rico to Chicago O'Hare Intl Airport
Our best Spirit Airlines deals on Puerto Rico to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines![Spirit Airlines]()
May 29![Spirit Airlines]()
Jun 1
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
ORD9:55 amChicago O'Hare Intl
8h 12m
1 stop
SJU7:07 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines![Spirit Airlines]()
May 30![Spirit Airlines]()
Jun 1
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
ORD9:55 amChicago O'Hare Intl
8h 12m
1 stop
SJU7:07 pmSan Juan Luis Munoz Marin Intl
Frontier flights from Puerto Rico to Chicago O'Hare Intl Airport
Our best Frontier deals on Puerto Rico to Chicago O'Hare Intl Airport flight tickets
Frontier![Frontier]()
May 7![Frontier]()
May 12
SJU7:30 pmSan Juan Luis Munoz Marin Intl
29h 02m
1 stop
ORD11:32 pmChicago O'Hare Intl
ORD4:15 pmChicago O'Hare Intl
17h 41m
1 stop
SJU10:56 amSan Juan Luis Munoz Marin Intl
Frontier![Frontier]()
May 8![Frontier]()
May 11
SJU4:39 pmSan Juan Luis Munoz Marin Intl
7h 53m
1 stop
ORD11:32 pmChicago O'Hare Intl
ORD4:15 pmChicago O'Hare Intl
6h 50m
1 stop
SJU12:05 amSan Juan Luis Munoz Marin Intl
See travel insights to Chicago from
How to get the cheapest flight ticket from Puerto Rico to Chicago O'Hare 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
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Other information
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $233.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Puerto Rico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $436.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Puerto Rico in the evening is the least expensive time of day to depart. momondo users have found prices as low as $241 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $473. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Puerto Rico to Chicago O'Hare Intl flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Puerto Rico - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Puerto Rico when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $304 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Puerto Rico for as low as $233 on momondo.
What cabin class options are available on Puerto Rico to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Puerto Rico to Chicago O'Hare Intl 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 O'Hare Intl?
Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Puerto Rico to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Puerto Rico according to our data. Spirit Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Puerto Rico to Chicago O'Hare Intl Airport on average per day?
6 flights are operational daily from Puerto Rico to Chicago O'Hare Intl Airport as of May 2025. The most popular departure time for this route is 7:00AM, with 56% of flights per day taking off in the afternoon.
How many flights depart from Puerto Rico to Chicago O'Hare Intl Airport on average per week?
As of May 2025, 46 flights take off from Puerto Rico and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
Cheap Puerto Rico to Chicago O'Hare Intl Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago O'Hare Intl Airport
When did momondo last update prices for flights from Puerto Rico to Chicago O'Hare Intl Airport?
Prices for flights from Puerto Rico to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Puerto Rico to Chicago O'Hare Intl Airport?
The number of operators available for flights from Puerto Rico to Chicago O'Hare Intl Airport is 6 as of May 2025.
How old do you have to be to fly from Puerto Rico to Chicago O'Hare 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 Puerto Rico to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Puerto Rico to Chicago O'Hare Intl Airport is Boeing 737 MAX 9 (29.51% of total bookings). The next most popular plane models are Airbus A320neo (27.43%), Airbus A321neo (17.91%), and Boeing 737-900 (15.67%).
Best airlines flying from Puerto Rico to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Puerto Rico to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $137 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $160 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $257 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $326 | Free Cancellation | Rating 7.2 10,000 reviews |
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Why use momondo?
Why should I use momondo to find a flight deal from Puerto Rico to Chicago?
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 Chicago from Puerto Rico.
Can I find flights from Puerto Rico to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Puerto Rico to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Puerto Rico to Chicago?
Once all potential Puerto Rico to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Puerto Rico to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Puerto Rico to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.
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