$91+ Cheap flights from O'Hare Intl (ORD) 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from O'Hare Intl to Puerto Rico with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 O'Hare Intl to Puerto Rico
Keep the following information in mind while searching for O'Hare Intl to Puerto Rico flight deals. Data was last updated January 15, 2026.
Round-trip from | $177 (CheapOair) |
|---|---|
One-way from | $91 (Priceline) |
Popular in | December |
Cheapest in | April |
Average price | $359 |
Good round-trip deal | $312 or less |
Good one-way deal | $133 or less |
Find flight deals from O'Hare Intl to Puerto Rico
Cheapest flights from O'Hare Intl to Puerto RicoExplore the most affordable flight options available from O'Hare Intl to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
Explore the most affordable flight options available from O'Hare Intl to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
This CheapOair deal was found by Cheapflights users on 1/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 1/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia 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 1/13. 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 JetBlue deal was found by Cheapflights users on 1/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This JetBlue deal was found by Cheapflights users on 1/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This JetBlue deal was found by Cheapflights users on 1/15. 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 JetBlue 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 1/12. 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 Cheapflightsfares deal was found by Cheapflights users on 1/13. 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 Cheapflightsfares 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 1/13. 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 JetBlue deal was found by Cheapflights users on 1/13. 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 JetBlue 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 1/14. 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.
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Sat 4/4
5:08 pm-1:58 am
1 stop7h 50m
Aguadilla Borinquen
Fri 4/10
3:55 am-9:02 am
1 stop30h 07m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 1/29
7:40 am-6:05 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Sat 2/7
9:25 am-7:31 pm
1 stop12h 06m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 1/23
9:15 am-7:26 pm
1 stop8h 11m
San Juan Luis Munoz Marin Intl
Fri 1/30
10:58 am-7:36 pm
1 stop10h 38m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/21
6:04 am-4:56 pm
1 stop8h 52m
San Juan Luis Munoz Marin Intl
Sat 2/28
5:10 am-12:04 pm
1 stop8h 54m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 2/19
12:01 pm-10:10 am
1 stop20h 09m
Ponce Mercedita
Mon 2/23
11:30 am-11:15 pm
1 stop13h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/1
10:00 am-10:01 pm
1 stop11h 01m
San Juan Luis Munoz Marin Intl
Wed 4/15
1:00 pm-9:36 pm
1 stop9h 36m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 4/8
10:12 am-8:55 am
1 stop21h 43m
Ponce Mercedita
Sun 4/12
10:50 am-12:29 am
1 stop14h 39m
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Mon 2/23
3:50 pm-2:57 am
1 stop9h 07m
Aguadilla Borinquen
Wed 2/25
3:58 am-10:46 am
1 stop8h 48m
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 2/26
11:55 am-10:10 am
1 stop20h 15m
Ponce Mercedita
Mon 3/2
11:30 am-11:15 pm
1 stop13h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 1/21
9:40 am-7:23 pm
1 stop7h 43m
San Juan Luis Munoz Marin Intl
Tue 1/27
11:06 am-7:36 pm
1 stop10h 30m
Best time to book a flight from O'Hare Intl to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from O'Hare Intl with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Puerto Rico
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $127). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $224). 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 ORD to PR?
Find hourly flight availability from O'Hare Intl 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 January 15, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Puerto Rico in the evening. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Puerto Rico. Price data was last updated on January 10, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Puerto Rico
Explore weekly flight availability from O'Hare Intl 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 January 15, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 139 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning 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?
Thursday 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 14% 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 January 15, 2026.
Read reviews from past customers who have flown United Airlines, American Airlines, and JetBlue from Chicago O'Hare Intl Airport to Puerto Rico. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Dane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from O'Hare Intl to Puerto Rico
Discover the top 7 airlines that operate flights from O'Hare Intl 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 January 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$290 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$262 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$309 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$253 | Average$522 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$362 | Average$535 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$385 | Average$486 | FlexibilityNo cancel fee | On-time63% |