$90+ Cheap flights from Chicago (CHI) to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Puerto Rico
Cheapest flights from Chicago to Puerto RicoExplore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.
Explore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.
This Trip.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 12/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Priceline deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FlightHub deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Priceline deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flight deals from Chicago to Puerto Rico
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated December 8, 2025.
Round-trip from | $181 (CheapOair) |
|---|---|
One-way from | $90 (Priceline) |
Popular in | December |
Cheapest in | April |
Average price | $592 |
Good round-trip deal | $303 or less |
Good one-way deal | $153 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sat 3/7
5:08 pm-8:55 am
1 stop13h 47m
Ponce Mercedita
Thu 3/12
10:50 am-12:29 am
1 stop14h 39m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sat 3/7
5:08 pm-8:55 am
1 stop13h 47m
Ponce Mercedita
Tue 3/10
10:50 am-12:29 am
1 stop14h 39m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 2/6
7:45 am-6:02 pm
1 stop8h 17m
San Juan Luis Munoz Marin Intl
Sat 2/14
5:22 pm-11:10 pm
1 stop7h 48m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 6/3
10:35 am-10:50 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Mon 6/8
3:30 am-2:20 pm
1 stop11h 50m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 5/21
3:15 pm-12:59 am
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Tue 5/26
12:30 pm-7:26 pm
1 stop7h 56m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Fri 3/6
5:08 pm-9:55 am
1 stop14h 47m
Ponce Mercedita
Tue 3/10
10:50 am-12:29 am
1 stop14h 39m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 1/15
8:51 pm-11:20 am
1 stop12h 29m
Ponce Mercedita
Sun 1/18
12:14 pm-11:26 am
1 stop25h 12m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sun 1/18
8:51 pm-11:20 am
1 stop12h 29m
Ponce Mercedita
Sat 1/24
1:50 pm-11:11 am
1 stop23h 21m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/23
3:15 pm-12:59 am
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Thu 5/28
12:30 pm-7:26 pm
1 stop7h 56m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 6/6
3:15 pm-12:59 am
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Sat 6/20
6:00 am-2:20 pm
1 stop9h 20m
Best time to book a flight from Chicago to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Puerto Rico
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $127). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $221). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to PR?
Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.
When flying from Chicago to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 46% versus a flight in the morning.
What is the cheapest day to fly from Chicago to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Puerto Rico. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Puerto Rico
Explore weekly flight availability from Chicago to Puerto Rico. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 8, 2025.
The most flights from CHI to PR0 are scheduled on a Saturday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 17% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 142 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated December 8, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Entertainment
Crew
Boarding
Comfort
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Puerto Rico
Discover the top 7 airlines that operate flights from Chicago to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$107 | Average$312 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$290 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$166 | Average$392 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$190 | Average$401 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$363 | Average$531 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$379 | Average$488 | FlexibilityNo cancel fee | On-time63% |