$113+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 7 — Jul 141
1 adult, Economy
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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
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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 July 2, 2025.
Round-trip from | $207 (Priceline) |
|---|---|
One-way from | $113 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $376 |
Good round-trip deal | $299 or less |
Good one-way deal | $190 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 July 2, 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 July 2, 2025.
This Priceline deal was found by Cheapflights users on 6/30. 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.
Mon 9/85:10 amORD - SJU
1 stop8h 01mFrontier
Thu 9/251:11 amSJU - ORD
1 stop11h 52mFrontier
Deal found 6/30![Frontier logo]()
$207
This FlightHub deal was found by Cheapflights users on 6/30. 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.
Sun 7/205:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Sat 8/22:28 pmSJU - ORD
Nonstop5h 19mSpirit Airlines
Deal found 6/30![Spirit Airlines logo]()
$213
This Priceline deal was found by Cheapflights users on 7/1. 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.
Fri 9/125:10 amORD - SJU
1 stop9h 41mMultiple Airlines
Tue 9/163:19 pmSJU - ORD
1 stop7h 39mMultiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$216
This Priceline deal was found by Cheapflights users on 6/30. 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.
Thu 8/74:37 pmORD - BQN
1 stop8h 24mFrontier
Sun 8/102:59 amBQN - ORD
1 stop22h 06mFrontier
Deal found 6/30![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 6/30. 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.
Sun 9/78:45 pmORD - PSE
1 stop11h 45mFrontier
Fri 9/2610:15 amPSE - ORD
1 stop10h 25mFrontier
Deal found 6/30![Frontier logo]()
$284
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Thu 7/3112:06 pmORD - PSE
1 stop11h 13mJetBlue
Mon 8/41:59 amPSE - ORD
1 stop10h 19mJetBlue
Deal found 6/30![JetBlue logo]()
$397
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Wed 8/135:16 pmORD - BQN
1 stop7h 45mMultiple Airlines
Sun 8/243:39 amBQN - ORD
2 stops17h 03mMultiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$430
This Expedia deal was found by Cheapflights users on 6/30. 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.
Wed 7/306:16 amORD - BQN
2 stops14h 17mJetBlue
Mon 8/45:01 amBQN - ORD
2 stops18h 27mJetBlue
Deal found 6/30![JetBlue logo]()
$458
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/37:17 amORD - BQN
2 stops14h 52mUnited Airlines
Tue 9/912:15 amBQN - ORD
1 stop10h 23mUnited Airlines
Deal found 7/1![United Airlines logo]()
$474
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:23 pmORD - MAZ
1 stop13h 51mMultiple Airlines
Sun 7/202:00 pmMAZ - ORD
2 stops19h 55mMultiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$483
This Trip.com deal was found by Cheapflights users on 6/30. 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.
Wed 7/911:28 amORD - PSE
1 stop19h 58mMultiple Airlines
Mon 7/149:16 amPSE - ORD
2 stops15h 37mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$508
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:23 pmORD - CPX
1 stop12h 36mMultiple Airlines
Mon 7/213:05 pmCPX - ORD
2 stops18h 50mMultiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$519
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 July 2, 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
Mon 9/8
5:10 am-2:11 pm
1 stop8h 01m
San Juan Luis Munoz Marin Intl
Thu 9/25
1:11 am-12:03 pm
1 stop11h 52m
$207
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 7/20
5:05 am-9:09 pm
1 stop15h 04m
San Juan Luis Munoz Marin Intl
Sat 8/2
2:28 pm-6:47 pm
Nonstop5h 19m
$213
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 9/12
5:10 am-3:51 pm
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Tue 9/16
3:19 pm-9:58 pm
1 stop7h 39m
$216
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Thu 8/7
4:37 pm-2:01 am
1 stop8h 24m
Aguadilla Borinquen
Sun 8/10
2:59 am-12:05 am
1 stop22h 06m
$244
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sun 9/7
8:45 pm-9:30 am
1 stop11h 45m
Ponce Mercedita
Fri 9/26
10:15 am-7:40 pm
1 stop10h 25m
$284
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 7/31
12:06 pm-12:19 am
1 stop11h 13m
Ponce Mercedita
Mon 8/4
1:59 am-11:18 am
1 stop10h 19m
$397
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 8/13
5:16 pm-2:01 am
1 stop7h 45m
Aguadilla Borinquen
Sun 8/24
3:39 am-7:42 pm
2 stops17h 03m
$430
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 7/30
6:16 am-9:33 pm
2 stops14h 17m
Aguadilla Borinquen
Mon 8/4
5:01 am-10:28 pm
2 stops18h 27m
$458
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 9/3
7:17 am-11:09 pm
2 stops14h 52m
Aguadilla Borinquen
Tue 9/9
12:15 am-9:38 am
1 stop10h 23m
$474
ChicagoMayagüez
ORD - MAZ
ORDMAZ
Chicago O'Hare Intl
Wed 7/16
6:23 pm-9:14 am
1 stop13h 51m
Mayagüez Eugenio M De Hostos
Sun 7/20
2:00 pm-8:55 am
2 stops19h 55m
$483
Showing 1-10 of 25 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 July 2, 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 July 2, 2025.
The most flights from ORD to PR0 are scheduled on a Wednesday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 July 2, 2025.
Read reviews from past customers who have flown United Airlines, JetBlue, and Spirit 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.
Boarding
7.7
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.0
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Boarding
7.7
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.0
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Boarding
7.7
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.0
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Boarding
7.7
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.0
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Boarding
7.7
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.0
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
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 July 2, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$302 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$294 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$212 | Average$394 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$264 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$287 | Average$418 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$338 | Average$512 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$385 | Average$486 | FlexibilityNo cancel fee | On-time63% |