HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Juan

$103+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to San Juan with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to San Juan are usually found in October or April, booked 42 days in advance, depart on a Tuesday or Monday 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 September 29, 2025.

Round-trip from

$195
(Kiwi.com)

One-way from

$103
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$381
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. 8% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mMultiple Airlines
Sat 11/15:51 pmSJU - ORD
1 stop21h 35mMultiple Airlines
Deal found 9/27$195
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Mon 11/38:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/27$196
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/28$199
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:28 pmORD - SJU
1 stop7h 16mSpirit Airlines
Fri 11/143:41 pmSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 9/28$200
This Priceline deal was found by Cheapflights users on 9/27. 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.
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Thu 10/231:59 amSJU - ORD
1 stop16h 41mMultiple Airlines
Deal found 9/27$203
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/28$205
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Sat 10/255:18 pmSJU - ORD
1 stop19h 15mSpirit Airlines
Deal found 9/28$206
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Wed 10/293:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/27$208
This Mytrip deal was found by Cheapflights users on 9/29. 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.
Sat 10/257:43 pmORD - SJU
1 stop14h 13mMultiple Airlines
Thu 10/303:04 amSJU - ORD
1 stop10h 22mMultiple Airlines
Deal found 9/29$209
This Orbitz deal was found by Cheapflights users on 9/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mMultiple Airlines
Thu 10/303:31 pmSJU - ORD
1 stop9h 08mMultiple Airlines
Deal found 9/28$211
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Wed 11/123:44 pmSJU - ORD
1 stop9h 22mSpirit Airlines
Deal found 9/28$212
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:20 amMDW - SJU
1 stop6h 51mFrontier
Sat 10/114:22 pmSJU - MDW
1 stop7h 25mFrontier
Deal found 9/28$271

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 September 29, 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

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

6:00 am-5:19 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:10 pm-9:46 pm

1 stop9h 36m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

7:35 am-7:05 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:10 am-11:35 am

1 stop7h 25m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/28

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 1/31

9:50 am-4:35 pm

1 stop8h 45m

$328

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/31

8:55 am-2:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Mon 11/3

4:52 pm-8:20 pm

Nonstop5h 28m

$342

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 10/29

7:10 am-11:32 am

Nonstop5h 22m

$342

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:05 am-9:05 am

1 stop9h 00m

$347

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/27

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Thu 10/30

4:50 pm-11:43 pm

1 stop7h 53m

$347

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 11/5

3:46 pm-11:10 pm

1 stop9h 24m

$347

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/22

10:35 am-8:38 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:10 am-11:32 am

Nonstop5h 22m

$347

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

7:30 am-11:50 pm

2 stops15h 20m

San Juan Luis Munoz Marin Intl

Sat 11/1

5:45 am-11:50 am

1 stop7h 05m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 37 results
1
2
3
4

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 September 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 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 September 29, 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 September 29, 2025.

The most flights from CHI to PR1 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Chicago to San Juan?

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 September 29, 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
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,050 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,158 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 4h 45m. Fly via Delta, Southwest, or United Airlines to get the fastest option. The distance between Chicago and San Juan is about 2073 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 Spirit Airlines, from $139, and Delta, from $196. 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?

    $119 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 Delta and Southwest, with prices starting from $132 and $132, 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: American Airlines (77%), Alaska Airlines (77%), Spirit Airlines (76%).

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

    Looking at all options, your cheapest flight can be booked for $101. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $127 on average, our data indicates $919 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$283FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$335FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$404FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$418FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$273Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$349Average$521FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$376Average$489FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.