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San Juan

$115+ Cheap flights from Chicago (CHI) 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in September or October, booked 42 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap flight deals from Chicago to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 August 14, 2025.

Round-trip from

$214
(FlightHub)

One-way from

$115
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$399
From Chicago (CHI) to San Juan
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One-way flight from Chicago (CHI) to San Juan
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Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to San Juan

Cheapest flights from Chicago to San Juan
Explore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Thu 9/2511:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Deal found 8/12$214
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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.
Sun 8/246:56 amORD - SJU
1 stop17h 00mSpirit Airlines
Thu 9/47:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/12$220
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Wed 8/271:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/12$221
This Expedia deal was found by Cheapflights users on 8/13. 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.
Mon 8/256:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Fri 9/57:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/13$223
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
Sun 8/245:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Fri 8/2910:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Deal found 8/13$225
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Tue 8/261:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/12$226
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 8/2512:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Fri 8/2910:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Deal found 8/12$229
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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.
Sun 8/315:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Sat 9/133:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 8/12$231
This Justfly.com deal was found by Cheapflights users on 8/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/245:05 amORD - SJU
1 stop15h 43mMultiple Airlines
Thu 9/43:16 pmSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 8/12$233
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
Sat 9/206:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Mon 9/297:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/13$234
This Priceline deal was found by Cheapflights users on 8/13. 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.
Mon 10/206:20 amMDW - SJU
1 stop6h 49mFrontier
Sat 10/254:18 pmSJU - MDW
1 stop8h 07mFrontier
Deal found 8/13$258
This Priceline deal was found by Cheapflights users on 8/12. 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.
Sat 9/2010:51 amMDW - SJU
1 stop12h 08mFrontier
Thu 9/253:16 pmSJU - MDW
1 stop9h 04mFrontier
Deal found 8/12$260

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

Fly from

Chicago

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/25

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Sat 8/30

4:05 pm-10:22 pm

1 stop7h 17m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/6

5:10 am-2:11 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Fri 10/10

7:40 pm-11:56 pm

Nonstop5h 16m

$253

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/25

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:40 pm-11:56 pm

Nonstop5h 16m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/17

6:30 am-2:11 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Mon 9/22

3:16 pm-12:10 am

1 stop9h 54m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

12:55 pm-6:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 9/5

7:40 pm-11:56 pm

Nonstop5h 16m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/8

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 10/13

7:40 pm-11:56 pm

Nonstop5h 16m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 10/16

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Sun 10/19

7:40 pm-11:56 pm

Nonstop5h 16m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/24

12:55 pm-6:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Thu 9/4

7:40 pm-11:56 pm

Nonstop5h 16m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 11/3

1:29 pm-8:14 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 11/7

2:38 pm-6:00 pm

Nonstop5h 22m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

12:55 pm-6:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 9/5

7:40 pm-11:56 pm

Nonstop5h 16m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 31 results
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Best time to book a flight from Chicago to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Chicago 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 to San Juan

How far ahead should I book a flight from Chicago to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Juan. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 42 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 to San Juan?

Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan (average of $254). Flying from Chicago 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 CHI to SJU?

Find hourly flight availability from Chicago 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 August 14, 2025.

It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 32% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Juan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago 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 to San Juan

Explore weekly flight availability from Chicago 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 August 14, 2025.

The most flights from CHI to PR1 are scheduled on a Thursday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 August 14, 2025.
Read through reviews of airlines operating flights from Chicago to San Juan, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,045 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to San Juan round-trip?

    Cheapflights users have booked flights from Chicago to San Juan round-trip from $106. Other airlines that can offer you cheap pricing are Spirit Airlines, from $139, and Delta, from $190. Frontier is priced at 72% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago to San Juan?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to San Juan on time: American Airlines (82%), Alaska Airlines (82%), Air Canada (79%).

  • What are the cheapest flights from Chicago to San Juan?

    Looking at all options, your cheapest flight can be booked for $116. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $250 on average our data indicates $561 when flying from Chicago to San Juan.

  • Can I find deals for flights from Chicago to San Juan that include hotel bookings?

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

  • How can I find direct flights from Chicago to San Juan?

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

  • Can I find deals for business class flights from Chicago to San Juan?

    Yes. Cheapflights offers flight deals from Chicago 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 to San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan (average of $254). Flying from Chicago 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 Chicago to San Juan

Discover the top 7 airlines that operate flights from Chicago 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$273FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$333FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$406FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$487FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$418FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$349Average$518FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$352Average$486FlexibilityNo cancel feeOn-time63%

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