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$113+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in September or August, booked 73 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap 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 July 31, 2025.

Round-trip from

$224
(Booking.com)

One-way from

$113
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$341
From Chicago O'Hare Intl to San Juan
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One-way flight from Chicago O'Hare Intl to San Juan
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Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from O'Hare Intl to San Juan

Cheapest flights from O'Hare Intl to San Juan
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 July 31, 2025.

This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Thu 8/147:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 7/30$224
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Sat 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sat 8/99:08 amORD - SJU
1 stop10h 21mFrontier
Wed 8/133:29 amSJU - ORD
1 stop12h 58mFrontier
Deal found 7/30$258

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to San Juan 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 31, 2025.
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

O'Hare Intl

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/10

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Thu 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

9:08 am-8:29 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Wed 8/20

8:13 pm-6:41 pm

1 stop23h 28m

$239

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/17

6:56 am-12:56 am

1 stop17h 00m

$113

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/9

12:20 pm-12:27 am

1 stop11h 07m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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.
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 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 July 25, 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 73 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 $254). Flying from Chicago O'Hare Intl Airport to San Juan 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 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 July 31, 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 32% 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 Tuesday evenings when fares are most often at their lowest. Thursday mornings 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 July 31, 2025.

The most flights from ORD to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

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 July 31, 2025.
See what other customers who have flown with Spirit Airlines and Frontier 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.
Spirit Airlines
6.3
Okay
8,049 reviews

Overall

6.3

Comfort

5.9

Crew

7.0

Boarding

6.6

Food

5.1

Entertainment

5.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2025

LAS - DTW

Was the most uncomfortable seat I have ever sat in on an airplane
Spirit Airlines
6.3
Okay
8,049 reviews
Spirit Airlines
6.3
Okay
8,049 reviews

Overall

6.3

Comfort

5.9

Crew

7.0

Boarding

6.6

Food

5.1

Entertainment

5.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2025

LAS - DTW

Was the most uncomfortable seat I have ever sat in on an airplane
Frontier
5.9
Fair
3,239 reviews
Spirit Airlines
6.3
Okay
8,049 reviews

Overall

6.3

Comfort

5.9

Crew

7.0

Boarding

6.6

Food

5.1

Entertainment

5.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2025

LAS - DTW

Was the most uncomfortable seat I have ever sat in on an airplane

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.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to San Juan round-trip?

    Flying on Spirit Airlines is currently your cheapest option to San Juan, with prices starting at $224. Another option worth looking into is Frontier, starting at $245 round trip. Spirit Airlines is 40% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to San Juan?

    Before booking your flight to San Juan from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: Air Canada (83%), United Airlines (83%), Air New Zealand( 83%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to San Juan?

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to San Juan? While on average our users pay $575, our data indicates the cheapest price to be $117. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $190.

  • Can I find deals for flights from O'Hare Intl to San Juan that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to San Juan.

  • Can I find deals for business class flights from O'Hare Intl to San Juan?

    Yes. Cheapflights offers flight deals from O'Hare Intl to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $254). Flying from Chicago O'Hare Intl Airport to San Juan 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.

See more FAQs

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$300FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$396FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$530FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$418FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$346Average$516FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$389Average$482FlexibilityNo cancel feeOn-time63%

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