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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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in January or April, booked 49 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 octubre 30, 2025.

Round-trip from

$209
(Frontier)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$371
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. 4% potential increase in price ($19 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 October 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 octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/204:51 pmORD - SJU
1 stop21h 37mMultiple Airlines
lun. 11/245:19 pmSJU - ORD
1 stop28h 02mMultiple Airlines
Deal found 10/30$210
This Priceline deal was found by Cheapflights users on 10/30. 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.
dom. 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
vie. 12/124:10 amSJU - ORD
1 stop8h 58mMultiple Airlines
Deal found 10/30$211
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
sáb. 11/224:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 10/30$212
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/278:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
jue. 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 10/30$213
This Priceline deal was found by Cheapflights users on 10/30. 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.
vie. 12/52:00 pmORD - SJU
1 stop18h 47mMultiple Airlines
dom. 12/78:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 10/30$214
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
jue. 11/274:05 pmSJU - ORD
1 stop10h 03mFrontier
Deal found 10/29$215
This Frontier deal was found by Cheapflights users on 10/30. 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.
jue. 12/117:40 amORD - SJU
1 stop10h 28mFrontier
sáb. 12/204:02 pmSJU - ORD
1 stop8h 44mFrontier
Deal found 10/30$216
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/288:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
jue. 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/30$217
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
sáb. 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/29$218
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/76:00 amORD - SJU
1 stop12h 08mFrontier
mié. 12/104:31 pmSJU - ORD
1 stop26h 56mFrontier
Deal found 10/29$219
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/148:26 amORD - SJU
2 stops15h 06mFrontier
sáb. 11/227:11 amSJU - ORD
1 stop12h 48mFrontier
Deal found 10/29$220
This Frontier deal was found by Cheapflights users on 10/30. 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.
dom. 12/76:00 amORD - SJU
1 stop12h 08mFrontier
vie. 12/123:55 amSJU - ORD
2 stops20h 29mFrontier
Deal found 10/30$221

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 octubre 30, 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

dom. 2/8

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

vie. 2/13

8:35 am-11:57 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

mié. 2/4

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 1/21

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

mié. 1/28

2:05 am-9:40 am

1 stop9h 35m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 1/19

2:49 pm-11:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

mar. 2/3

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/18

5:33 am-5:17 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

vie. 1/30

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 1/19

2:49 pm-11:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

sáb. 1/31

7:30 am-1:49 pm

1 stop8h 19m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 1/24

10:24 am-11:59 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

vie. 1/30

7:00 am-5:45 pm

1 stop12h 45m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 2/22

5:45 am-4:36 pm

1 stop8h 51m

San Juan Luis Munoz Marin Intl

vie. 2/27

2:05 am-9:36 am

1 stop9h 31m

$262

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

vie. 1/30

8:35 am-11:57 am

Nonstop5h 22m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 1/13

5:40 am-4:36 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

lun. 1/19

2:05 am-10:53 am

1 stop10h 48m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 21 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 October 24, 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, February 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 $188). 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 octubre 30, 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 10% 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 Saturday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 octubre 30, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines 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.
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,116 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,122 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • How long is the flight from Chicago O'Hare Intl Airport to San Juan?

    A quick flight from Chicago O'Hare Intl Airport to San Juan can take about 4h 40m. United Airlines provides one of the quickest options available for as low as $218. Chicago O'Hare Intl Airport and San Juan are separated by a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Frontier is currently your cheapest option to San Juan, with prices starting at $106. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Delta, with the lowest prices starting at $140 and $196, respectively. Frontier is 72% 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: American Airlines (91%), Alaska Airlines (82%), Spirit Airlines( 78%).

  • 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 $813, our data indicates the cheapest price to be $124. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $192.

  • 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, February 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 $188). 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$284FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$308FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$396FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$273Average$532FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$524FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$385Average$478FlexibilityNo cancel feeOn-time63%

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