$116+ Cheap flights from O'Hare Intl (ORD) to San Juan
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 1/31. 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 San Juan 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.Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in April or January, booked 49 days in advance, depart on a Monday or Tuesday and return on a Friday
Cheap flight deals from O'Hare Intl to San Juan
Cheapest flights from O'Hare Intl to San JuanExplore the most affordable flight options available from O'Hare Intl to San Juan. 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 O'Hare Intl to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
This JetBlue 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 JetBlue 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 12/15. 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 Frontier 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 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 CheapOair 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 12/16. 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 Priceline 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 12/15. 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 Priceline 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 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines 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 American Airlines 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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flight deals from O'Hare Intl to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.
Round-trip from | $195 (Kiwi.com) |
|---|---|
One-way from | $116 (Travelocity) |
Popular in | December |
Cheapest in | April |
Average price | $538 |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 3/10
10:00 am-8:56 pm
1 stop9h 56m
San Juan Luis Munoz Marin Intl
Thu 3/12
3:26 am-11:25 am
1 stop8h 59m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 3/24
10:56 am-11:23 pm
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Thu 3/26
3:26 am-11:25 am
1 stop8h 59m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
10:35 am-8:03 pm
1 stop8h 28m
San Juan Luis Munoz Marin Intl
Tue 5/12
12:30 pm-7:26 pm
1 stop7h 56m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 2/27
12:41 pm-11:44 pm
1 stop9h 03m
San Juan Luis Munoz Marin Intl
Sat 3/7
5:10 am-11:58 am
1 stop8h 48m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 3/9
12:41 pm-9:31 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 3/11
1:30 am-10:05 am
1 stop9h 35m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 1/18
7:45 am-6:05 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Fri 1/23
11:06 am-7:36 pm
1 stop10h 30m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 3/17
10:56 am-11:23 pm
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Thu 3/19
1:30 am-10:05 am
1 stop9h 35m
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
Mon 3/9
12:41 pm-9:31 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Thu 3/12
3:26 am-11:25 am
1 stop8h 59m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 2/4
7:45 am-6:02 pm
1 stop8h 17m
San Juan Luis Munoz Marin Intl
Sat 2/7
1:30 pm-7:45 pm
1 stop8h 15m
Best time to book a flight from O'Hare Intl to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan
How far ahead should I book a flight from Chicago O'Hare Intl Airport to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to San Juan. Price data was last updated on December 12, 2025.
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San Juan, you should look to book at least 49 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to San Juan?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $127). Flying from Chicago O'Hare Intl Airport to San Juan 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 ORD to SJU?
Find hourly flight availability from O'Hare Intl to San Juan. 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.
It’s optimal to fly from Chicago O'Hare Intl Airport to San Juan in the evening. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to San Juan?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to San Juan. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Thursday at noon 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 O'Hare Intl Airport to San Juan
Explore weekly flight availability from O'Hare Intl to San Juan. 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 ORD to PR1 are scheduled on a Tuesday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San Juan?
How often are flights from Chicago to San Juan delayed?
About 17% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 144 minutes.
What is the most punctual flight time for Chicago to San Juan 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 San Juan 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 San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated December 18, 2025.
See what other customers who have flown with United Airlines, American Airlines, and JetBlue from Chicago O'Hare Intl Airport to San Juan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Entertainment
Boarding
Overall
Food
Crew
Comfort
Reviews
Kevin,Dec 2025
BOS - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to San Juan. 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 San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from O'Hare Intl to San Juan
Discover the top 7 airlines that operate flights from O'Hare Intl to San Juan. 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$108 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$313 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$190 | Average$396 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$287 | Average$537 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$363 | Average$532 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$385 | Average$485 | FlexibilityNo cancel fee | On-time63% |