$115+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
ago. 19 — ago. 261
1 adult, Economy
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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 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 agosto 14, 2025.
Round-trip from | $214 (FlightHub) |
|---|---|
One-way from | $115 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $399 |
Good round-trip deal | $274 or less |
Good one-way deal | $150 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 agosto 14, 2025.
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 agosto 14, 2025.
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/206:30 amORD - SJU
1 stop6h 41mSpirit Airlines
jue. 9/2511:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/246:56 amORD - SJU
1 stop17h 00mSpirit Airlines
jue. 9/47:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$220
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
mié. 8/271:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$221
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/256:56 amORD - SJU
1 stop16h 01mSpirit Airlines
vie. 9/57:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/13![Spirit Airlines logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
dom. 8/245:05 amORD - SJU
1 stop15h 43mSpirit Airlines
vie. 8/2910:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Deal found 8/13![Spirit Airlines logo]()
$225
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
mar. 8/261:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/2512:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
vie. 8/2910:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/315:05 amORD - SJU
1 stop15h 43mSpirit Airlines
sáb. 9/133:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 8/12![Spirit Airlines logo]()
$231
This Justfly.com deal was found by Cheapflights users on 8/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/245:05 amORD - SJU
1 stop15h 43mMultiple Airlines
jue. 9/43:16 pmSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 8/12![Multiple Airlines logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
sáb. 9/206:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
lun. 9/297:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/13![Spirit Airlines logo]()
$234
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/208:00 amORD - BQN
1 stop17h 27mFrontier
vie. 9/263:32 amBQN - ORD
1 stop12h 45mFrontier
Deal found 8/12![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
jue. 9/188:49 pmORD - BQN
1 stop28h 38mFrontier
dom. 9/213:32 amBQN - ORD
1 stop17h 12mFrontier
Deal found 8/12![Frontier logo]()
$267
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
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
O'Hare Intl
Fly to
Puerto Rico
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
lun. 8/25
6:56 am-11:57 pm
1 stop16h 01m
San Juan Luis Munoz Marin Intl
sáb. 8/30
4:05 pm-10:22 pm
1 stop7h 17m
$235
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
lun. 10/6
5:10 am-2:11 pm
1 stop8h 01m
San Juan Luis Munoz Marin Intl
vie. 10/10
7:40 pm-11:56 pm
Nonstop5h 16m
$253
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
jue. 9/25
12:55 pm-6:34 pm
Nonstop4h 39m
San Juan Luis Munoz Marin Intl
lun. 9/29
7:40 pm-11:56 pm
Nonstop5h 16m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mié. 9/17
6:30 am-2:11 pm
1 stop6h 41m
San Juan Luis Munoz Marin Intl
lun. 9/22
3:16 pm-12:10 am
1 stop9h 54m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
dom. 8/31
12:55 pm-6:40 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
vie. 9/5
7:40 pm-11:56 pm
Nonstop5h 16m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mié. 10/8
12:55 pm-6:34 pm
Nonstop4h 39m
San Juan Luis Munoz Marin Intl
lun. 10/13
7:40 pm-11:56 pm
Nonstop5h 16m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
jue. 10/16
12:55 pm-6:34 pm
Nonstop4h 39m
San Juan Luis Munoz Marin Intl
dom. 10/19
7:40 pm-11:56 pm
Nonstop5h 16m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
dom. 8/24
12:55 pm-6:40 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
jue. 9/4
7:40 pm-11:56 pm
Nonstop5h 16m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
lun. 11/3
1:29 pm-8:14 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
vie. 11/7
2:38 pm-6:00 pm
Nonstop5h 22m
$255
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
sáb. 8/30
12:55 pm-6:40 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
vie. 9/5
7:40 pm-11:56 pm
Nonstop5h 16m
$255
Showing 1-10 of 52 results
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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
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 $254). Flying from Chicago O'Hare Intl Airport to Puerto Rico in June is currently the most expensive (average of $339). 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 agosto 14, 2025.
When flying from Chicago O'Hare Intl Airport to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 agosto 14, 2025.
The most flights from ORD to PR0 are scheduled on a Thursday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
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 agosto 14, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines 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.
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Crew
8.5
Food
7.3
Boarding
8.2
Comfort
7.9
Overall
8.0
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
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 agosto 14, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$311 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$301 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$190 | Average$398 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$526 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$287 | Average$418 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$349 | Average$518 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$389 | Average$483 | FlexibilityNo cancel fee | On-time63% |