$90+ Cheap flights from Puerto Rico to O'Hare Intl (ORD)
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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Puerto Rico to O'Hare Intl 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 Puerto Rico to O'Hare Intl
Cheapest flights from Puerto Rico to O'Hare IntlExplore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
Explore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
This Mytrip deal was found by Cheapflights users on 12/16. 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.
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/15. 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 Cheapflightsfares 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 12/16. 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 Frontier deal was found by Cheapflights users on 12/16. 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 Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.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 12/17. 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 Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com deal was found by Cheapflights users on 12/16. 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 Expedia deal was found by Cheapflights users on 12/16. 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.
Find flight deals from Puerto Rico to O'Hare Intl
Keep the following information in mind while searching for Puerto Rico to O'Hare Intl flight deals. Data was last updated December 18, 2025.
Round-trip from | $169 (CheapOair) |
|---|---|
One-way from | $90 (Expedia) |
Popular in | December |
Cheapest in | February |
Average price | $428 |
Good round-trip deal | $271 or less |
Good one-way deal | $159 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Puerto Rico to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/5
11:06 am-7:31 pm
1 stop10h 25m
Chicago O'Hare Intl
Sun 2/8
7:45 am-6:02 pm
1 stop8h 17m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
1:00 pm-9:33 pm
1 stop9h 33m
Chicago O'Hare Intl
Tue 4/14
1:45 pm-1:47 am
1 stop11h 02m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 2/25
8:35 am-11:57 am
Nonstop5h 22m
Chicago O'Hare Intl
Mon 3/9
2:20 pm-8:00 pm
Nonstop4h 40m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/24
1:30 am-10:05 am
1 stop9h 35m
Chicago O'Hare Intl
Sun 3/29
10:56 am-11:23 pm
1 stop11h 27m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/22
1:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Thu 1/29
12:17 pm-6:49 pm
Nonstop4h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 5/13
12:30 pm-7:26 pm
1 stop7h 56m
Chicago O'Hare Intl
Tue 5/26
3:15 pm-1:59 am
1 stop9h 44m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 1/21
4:52 pm-8:20 pm
Nonstop5h 28m
Chicago O'Hare Intl
Sat 1/24
2:20 pm-9:00 pm
Nonstop4h 40m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Mon 3/2
12:22 pm-6:54 pm
Nonstop4h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/21
2:15 am-6:15 pm
1 stop17h 00m
Chicago O'Hare Intl
Sun 4/26
12:22 pm-5:54 pm
Nonstop4h 32m
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Mon 12/29
6:42 pm-9:02 am
1 stop16h 20m
Chicago O'Hare Intl
Fri 1/2
10:12 am-3:10 am
1 stop14h 58m
Best time to book a flight from Puerto Rico to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Puerto Rico with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago O'Hare Intl Airport
What is the cheapest month to book a flight from Puerto Rico to Chicago O'Hare Intl Airport?
Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $121). Flying from Puerto Rico to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $175). 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 PR to ORD?
Find hourly flight availability from Puerto Rico to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.
A simple way to save on the total cost of your ticket is to fly from Puerto Rico to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Puerto Rico to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to O'Hare Intl. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Puerto Rico to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Puerto Rico to Chicago O'Hare Intl Airport
Explore weekly flight availability from Puerto Rico to O'Hare Intl. 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 18, 2025.
The most flights from PR0 to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 9% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 169 minutes.
What is the most punctual flight time for Puerto Rico to Chicago 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 Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Puerto Rico to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and JetBlue from Puerto Rico to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Food
Crew
Boarding
Overall
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
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Alternative routes for Puerto Rico to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Puerto Rico to O'Hare Intl
Discover the top 7 airlines that operate flights from Puerto Rico to O'Hare Intl. 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 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$280 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$271 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$341 | Average$479 | FlexibilityNo cancel fee | On-time63% |