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San Juan

$104+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in April or January, booked 45 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap 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 December 30, 2025.

This Priceline deal was found by Cheapflights users on 12/27. 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.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Thu 1/86:30 amSJU - ORD
1 stop10h 58mMultiple Airlines
Deal found 12/27$232
This Priceline deal was found by Cheapflights users on 12/27. 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.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Wed 1/79:19 pmSJU - ORD
1 stop20h 09mMultiple Airlines
Deal found 12/27$238
This JetBlue deal was found by Cheapflights users on 12/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mJetBlue
Sat 1/108:00 amSJU - ORD
1 stop11h 43mJetBlue
Deal found 12/28$242
This Expedia deal was found by Cheapflights users on 12/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop7h 41mJetBlue
Thu 1/811:06 amSJU - ORD
1 stop10h 30mJetBlue
Deal found 12/30$243
This JetBlue deal was found by Cheapflights users on 12/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mJetBlue
Thu 1/1511:06 amSJU - ORD
1 stop10h 30mJetBlue
Deal found 12/30$286
This Expedia deal was found by Cheapflights users on 12/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop7h 41mMultiple Airlines
Fri 1/97:10 amSJU - ORD
1 stop11h 57mMultiple Airlines
Deal found 12/30$288
This American Airlines deal was found by Cheapflights users on 12/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:40 amORD - SJU
1 stop11h 03mAmerican Airlines
Thu 1/154:28 pmSJU - ORD
Nonstop5h 32mAmerican Airlines
Deal found 12/28$291
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:46 amORD - SJU
1 stop10h 34mDelta
Thu 1/157:00 amSJU - ORD
1 stop8h 14mDelta
Deal found 12/28$295
This Priceline deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Fri 1/93:55 amSJU - ORD
1 stop17h 22mMultiple Airlines
Deal found 12/30$302
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Sun 1/1110:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/29$336
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Fri 1/95:45 amSJU - MDW
1 stop10h 21mFrontier
Deal found 12/29$348
This CheapOair deal was found by Cheapflights users on 12/28. 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.
Tue 12/303:10 pmMDW - SJU
1 stop22h 49mFrontier
Thu 1/810:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/28$394

Find 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 December 30, 2025.

Round-trip from

$192
(CheapOair)

One-way from

$104
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$562
From Chicago (CHI) to San Juan
Search Deals
One-way flight from Chicago (CHI) to San Juan
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 30, 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

Fri 2/27

12:41 pm-12:29 am

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Wed 2/4

9:25 am-7:36 pm

1 stop12h 11m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

9:40 am-7:26 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Tue 1/27

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/7

12:51 pm-11:44 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Sun 3/15

1:30 am-10:05 am

1 stop9h 35m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/4

6:45 am-4:26 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/23

9:15 am-7:26 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

Tue 1/27

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

2:50 pm-11:45 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 1/30

3:55 pm-9:00 pm

1 stop7h 05m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/22

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:22 pm

1 stop8h 27m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Sat 1/24

7:30 am-3:38 pm

1 stop10h 08m

$225

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

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 43 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 December 26, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 45 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 $127). Flying from Chicago 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 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 December 30, 2025.

It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 33% 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 February 10, 2025.

Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday at noon 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 December 30, 2025.

The most flights from CHI to PR1 are scheduled on a Monday (12 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Chicago 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 142 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 30, 2025.
Read through reviews of airlines operating flights from Chicago to San Juan, such as United Airlines, American Airlines, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,124 reviews
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,074 reviews
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
JetBlue
7.2
Good
2,903 reviews
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Spirit Airlines
6.3
Okay
8,238 reviews
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Frontier
5.7
Fair
3,067 reviews
United Airlines
7.4
Good
9,124 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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.

  • How long is the flight from Chicago to San Juan?

    There are many flights that can get you from Chicago to San Juan in 8h 45m. Fly via JetBlue, Delta, or Southwest to get the fastest option. The distance between Chicago and San Juan is about 2057 mi. This flight may include one or multiple stops.

  • 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 JetBlue, from $124, and Delta, from $136. Frontier is priced at 73% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to San Juan one-way?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Spirit Airlines, with prices starting from $84 and $92, respectively.

  • 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: Air Canada (80%), United Airlines (80%), Air New Zealand (80%).

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

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $136 on average, our data indicates $714 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 $127). Flying from Chicago 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.

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 December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$115Average$288FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$136Average$297FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$314FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$400FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$282Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$362Average$531FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$379Average$487FlexibilityNo cancel feeOn-time63%

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