Best time to go: what is the RIGHT price for a round-trip flight to Puerto Rico (San Juan) (from: Chicago)

The average price to go to Puerto Rico (San Juan) from Chicago airport is $ 402 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 272 (in september) and $ 581 (in march), which is a saving of $ 130 or a surplus of $ 180 (compared to the average price) depending on the period you leave.

The analysis of all prices reveals that the most frequent price is between $209 to $261 and it is generally more economical to leave on a tuesday and return on a wednesday on a flight with 1 or more layovers.

Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Puerto Rico (San Juan) before booking your flight.

If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Puerto Rico (San Juan) plane ticket.

How are these data calculated?

We have studied a sample of 60000 airfare prices from previous years for flights to Puerto Rico (San Juan) from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.

Average price depending on the departure month

Data analysis:

By leaving in september, the price of the plane ticket will statistically be the cheapest ($ 272, saving $ 130 compared to the average price over the year which is $ 402). Conversely, march will be the most expensive ($ 581).

Flight Chicago-Puerto Rico (San Juan): when is the best time to go for the best price?

Month Good price* Average price Our opinion
January$ 222 $ 345 good price
February$ 228 $ 348 good price
March$ 377 $ 581 very high price
April$ 306 $ 444 fair price
May$ 278 $ 355 good price
June$ 351 $ 469 high price
July$ 337 $ 437 fair price
August$ 243 $ 354 good price
September$ 215 $ 272 very good price
October$ 228 $ 300 good price
November$ 265 $ 420 fair price
December$ 296 $ 491 high price

*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!

Price breakdown to travel from Chicago to Puerto Rico (San Juan)

Data analysis:

The prices for flights from Chicago to Puerto Rico (San Juan) range from $104 to $886. 4% of tickets were purchased at the minimum price (from $105 to $157), 1% at the maximum price (from $834 to $886). The majority of plane tickets were purchased in the range of $209 to $261 (15% of tickets).

Cheapest airlines for the Chicago->Puerto Rico flight

There are 7 companies that serve Chicago from Puerto Rico (San Juan) airport: Spirit Airlines, Frontier Airlines, United, American Airlines, jetBlue, Alaska Airlines and Air New Zealand.

Data analysis:

Of the 60000 flights analyzed in previous years, Spirit Airlines was the airline that offered the best fare most often in the flight ticket search results (38% of the time) on the Chicago->Puerto Rico route.

Direct flight or flight with layover?

Data analysis:

To get the best price for the Chicago-Puerto Rico (San Juan) flight, you should take a flight with one or more layovers (you will save an average of $ 68 compared to a direct flight).

Which day of the week to leave?

Data analysis:

Statistically, Chicago-Puerto Rico (San Juan) flights departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday as your departure date, you can save an average of $41. On the other hand, departing on a saturday may cost you an additional $44.

Which day of the week to come back?

Data analysis:

Statistically, return flights from Puerto Rico (San Juan) to Chicago departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday for your return date, you will save an average of $59. Conversely, departing from Puerto Rico (San Juan) on a sunday may cost you an additional $58.


Top prices Chicago-Puerto Rico (San Juan)

Round tripDatesPrice
Chicago → San Juan07-12 to 12-12-2024$ 157 
Chicago → San Juan08-12 to 13-12-2024$ 166 
Chicago → San Juan09-12 to 16-12-2024$ 145 
Chicago → San Juan16-12 to 25-12-2024$ 146 
Chicago → San Juan08-01 to 22-01-2025$ 129 
Chicago → San Juan01-02 to 05-02-2025$ 159 
Chicago → San Juan04-02 to 08-02-2025$ 159 
Chicago → San Juan05-02 to 12-02-2025$ 129 
Chicago → San Juan07-02 to 15-02-2025$ 166 
Chicago → San Juan12-02 to 22-02-2025$ 153 


When to book your flight Chicago - Puerto Rico (San Juan) to get the cheapest price?

Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 11 to 12 months in advance.

Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Puerto Rico flight, it is recommended to book your ticket on a friday.

How far in advance should I buy my flight?

Data analysis:

To get the cheapest flight ticket from Chicago to Puerto Rico (San Juan), it is recommended to buy it 1 to 2 months before departure (it is then on average 271 $, which is a saving of 131 $ compared to the overall average price). On the other hand, if you buy your ticket 11 to 12 months in advance, you will pay the full price (1452 $ more than the average price).

Depending on the departure month

The best time to buy your Chicago to Puerto Rico (San Juan) flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.

Departure on... How far in advance should I book?
January

Best time: 1 to 2 months before departure (average price: 184 $)

Other interesting period(s): 0 to 1 month ($ 334), 2 to 3 months ($ 216), 3 to 4 months ($ 265), 4 to 5 months ($ 327)

February

Best time: 2 to 3 months before departure (average price: 221 $)

Other interesting period(s): 1 to 2 months ($ 279), 3 to 4 months ($ 241), 4 to 5 months ($ 251), 5 to 6 months ($ 305)

March

Best time: 3 to 4 months before departure (average price: 409 $)

Other interesting period(s): 0 to 1 month ($ 473), 1 to 2 months ($ 447), 2 to 3 months ($ 410)

April

Best time: 0 to 1 month before departure (average price: 316 $)

Other interesting period(s): 1 to 2 months ($ 346), 2 to 3 months ($ 417), 3 to 4 months ($ 389)

May

Best time: 1 to 2 months before departure (average price: 278 $)

Other interesting period(s): 0 to 1 month ($ 287), 2 to 3 months ($ 280)

June

Best time: 0 to 1 month before departure (average price: 281 $)

Other interesting period(s): 1 to 2 months ($ 285), 2 to 3 months ($ 346)

July

Best time: 0 to 1 month before departure (average price: 256 $)

Other interesting period(s): 1 to 2 months ($ 272), 2 to 3 months ($ 355), 3 to 4 months ($ 431)

August

Best time: 1 to 2 months before departure (average price: 213 $)

Other interesting period(s): 0 to 1 month ($ 224), 2 to 3 months ($ 263), 3 to 4 months ($ 294)

September

Best time: 1 to 2 months before departure (average price: 212 $)

Other interesting period(s): 0 to 1 month ($ 258), 2 to 3 months ($ 218), 3 to 4 months ($ 232), 4 to 5 months ($ 269)

October

Best time: 2 to 3 months before departure (average price: 234 $)

Other interesting period(s): 1 to 2 months ($ 242), 3 to 4 months ($ 268), 6 to 7 months ($ 292)

November

Best time: 1 to 2 months before departure (average price: 248 $)

Other interesting period(s): 0 to 1 month ($ 338), 2 to 3 months ($ 280), 3 to 4 months ($ 321), 4 to 5 months ($ 385)

December

Best time: 1 to 2 months before departure (average price: 227 $)

Other interesting period(s): 0 to 1 month ($ 281), 2 to 3 months ($ 351), 3 to 4 months ($ 425), 4 to 5 months ($ 464)

What day of the week should I book my flight ticket?

Data analysis:

Statistically, friday is the day when plane tickets for Chicago->Puerto Rico are the cheapest. So, by buying your plane ticket on a friday, you will save $6. Conversely, by buying it on a tuesday, you may end up paying $8 more.



Chicago to Puerto Rico (San Juan): flight price when booking today

Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.

Month Current price
November 2024$ 360
$222 to $481
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December 2024$ 298
$145 to $529
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January 2025$ 262
$129 to $595
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February 2025$ 235
$129 to $366
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March 2025$ 618
$293 to $1036
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April 2025$ 627
$332 to $2141
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May 2025$ 298
$188 to $714
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June 2025$ 468
$400 to $661
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July 2025$ 486
$369 to $720
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August 2025$ 438
$341 to $512
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October 2025$ 455
$411 to $491
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Data analysis:

Compared to the average price, november, december, january, february and may are cheaper to travel to Puerto Rico (San Juan). So it may be interesting to book now to leave during these months!



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