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$104+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in August or May, booked 30 days in advance, depart on a Tuesday or Monday 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 April 29, 2025.

Round-trip from

$195
(Cheapflightsfares)

One-way from

$104
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$338
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. 11% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/129:55 amORD - SJU
1 stop7h 55mSpirit Airlines
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/29$202
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/114:15 pmORD - SJU
1 stop20h 14mFrontier
Fri 5/163:56 amSJU - ORD
1 stop20h 36mFrontier
Deal found 4/29$270
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Thu 5/1511:30 amORD - SJU
Nonstop4h 46mMultiple Airlines
Mon 5/196:00 amSJU - ORD
1 stop13h 29mMultiple Airlines
Deal found 4/28$275
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/134:03 pmORD - SJU
1 stop8h 46mJetBlue
Tue 5/208:00 amSJU - ORD
1 stop11h 36mJetBlue
Deal found 4/29$333

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 April 29, 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

Mon 5/12

9:55 am-6:50 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/11

4:15 pm-1:29 pm

1 stop20h 14m

San Juan Luis Munoz Marin Intl

Fri 5/16

3:56 am-11:32 pm

1 stop20h 36m

$270

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/15

11:30 am-5:16 pm

Nonstop4h 46m

San Juan Luis Munoz Marin Intl

Mon 5/19

6:00 am-6:29 pm

1 stop13h 29m

$275

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/13

4:03 pm-1:49 am

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Tue 5/20

8:00 am-6:36 pm

1 stop11h 36m

$333

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/15

11:30 am-5:16 pm

Nonstop4h 46m

$104

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/12

4:15 pm-12:05 am

1 stop6h 50m

$135

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/31

9:08 pm-9:58 am

1 stop11h 50m

$143

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 7/23

8:40 am-6:47 pm

1 stop9h 07m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 7/16

1:50 pm-11:55 pm

2 stops9h 05m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 7/10

6:03 pm-11:54 pm

Nonstop4h 51m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 12 results
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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 April 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 30 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 December is currently the most expensive (average of $336). 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 April 29, 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 28% 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 Wednesday evenings when fares are most often at their lowest. Sunday afternoons 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 April 29, 2025.

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

Rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Juan ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan when rainfall is around 2.2 in.

Temperature in San Juan by month

Plan your trip to San Juan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to San Juan by reading reviews from past customers. 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.
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $195. Additional round-trip tickets that might be worth considering are offered by Frontier and JetBlue, with the lowest prices starting at $270 and $324, respectively. Spirit Airlines is 46% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to San Juan one-way?

    $104 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and JetBlue, with prices starting from $135 and $162, respectively.

  • 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: United Airlines (88%), American Airlines (83%), Air Canada( 82%).

  • 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 $757, our data indicates the cheapest price to be $133. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $188.

  • Where are the most common layover locations when flying from Chicago O'Hare Intl Airport to San Juan?

    Most of the time, Chicago O'Hare Intl Airport to San Juan flights that have layovers will stop in Orlando.

  • What are some popular things to do or see while on a layover in Orlando?

    Walt Disney World Resort, Universal Orlando Resort, and International Drive are the most popular attractions in Orlando if you're in need of something to do during your layover. Walt Disney World Resort, Universal Orlando Resort, and International Drive are located about 16.2 mi, 10.2 mi, and 9.9 mi, respectively from Orlando. Those landing in Orlando looking to spend some time exploring during their layover can rent a car for about $26 per day.

  • Where are the least popular layover locations for Chicago O'Hare Intl Airport to San Juan flights?

    Chicago O'Hare Intl Airport to San Juan flights have a layover in Charlotte least often.

  • 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 December is currently the most expensive (average of $336). 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$211FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$273FlexibilityNo cancel feeOn-time65%
DeltaCheapest$216Average$394FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$271Average$522FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$404FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$335Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$385Average$483FlexibilityNo cancel feeOn-time63%

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