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$95+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in August or September, booked 53 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 April 22, 2025.

Round-trip from

$189
(eDestinos)

One-way from

$95
(eDestinos)

Popular in

December

Cheapest in

August

Average price

$352
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. 15% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 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 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 April 22, 2025.

This eDestinos deal was found by Cheapflights users on 4/21. 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 5/1111:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Thu 5/156:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 4/21$189
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Sat 5/34:15 pmORD - SJU
1 stop9h 36mMultiple Airlines
Sat 5/108:12 pmSJU - ORD
1 stop13h 38mMultiple Airlines
Deal found 4/22$248
This Frontier deal was found by Cheapflights users on 4/22. 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.
Fri 5/29:00 amORD - SJU
1 stop8h 47mFrontier
Mon 5/56:00 amSJU - ORD
1 stop13h 29mFrontier
Deal found 4/22$298
This Frontier deal was found by Cheapflights users on 4/21. 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.
Mon 5/56:15 amMDW - SJU
1 stop7h 32mFrontier
Wed 5/73:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/21$298
This Delta deal was found by Cheapflights users on 4/21. 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.
Sun 8/316:00 amORD - SJU
1 stop9h 50mDelta
Fri 9/122:28 pmSJU - ORD
1 stop10h 25mDelta
Deal found 4/21$307
This Trip.com deal was found by Cheapflights users on 4/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1912:15 pmMDW - SJU
1 stop12h 35mMultiple Airlines
Sat 5/2412:36 pmSJU - MDW
1 stop10h 26mMultiple Airlines
Deal found 4/20$337
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 9/3010:35 amMDW - SJU
1 stop10h 33mDelta
Sat 10/412:55 pmSJU - MDW
1 stop9h 49mDelta
Deal found 4/21$344
This JetBlue deal was found by Cheapflights users on 4/21. 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 8/278:40 amORD - SJU
1 stop9h 07mJetBlue
Sat 9/136:00 amSJU - ORD
1 stop7h 40mJetBlue
Deal found 4/21$353
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/271:00 pmMDW - SJU
2 stops8h 30mSouthwest
Tue 6/31:55 pmSJU - MDW
1 stop9h 10mSouthwest
Deal found 4/21$381

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 April 22, 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

Sun 5/11

11:30 am-5:16 pm

Nonstop4h 46m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:09 am-10:25 am

Nonstop5h 16m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/3

4:15 pm-2:51 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Sat 5/10

8:12 pm-8:50 am

1 stop13h 38m

$248

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/2

9:00 am-6:47 pm

1 stop8h 47m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

$298

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/5

6:15 am-2:47 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-12:24 pm

1 stop9h 28m

$298

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/19

12:15 pm-1:50 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Sat 5/24

12:36 pm-10:02 pm

1 stop10h 26m

$337

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/29

8:45 am-5:30 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 6/3

7:01 am-3:04 pm

1 stop9h 03m

$353

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/27

1:00 pm-10:30 pm

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Tue 6/3

1:55 pm-10:05 pm

1 stop9h 10m

$381

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 5/3

9:52 am-8:23 pm

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:15 am-4:12 pm

1 stop10h 57m

$421

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/12

11:30 am-5:16 pm

Nonstop4h 46m

$95

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/12

6:15 am-2:47 pm

1 stop7h 32m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 20 results
1
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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 April 18, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 53 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 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 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 April 22, 2025.

It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 28% 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 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 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 April 22, 2025.

The most flights from CHI to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 22, 2025.
To help decide which airline to fly from Chicago to San Juan, see what other customers have to say about Southwest, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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
8,683 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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
2,923 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,287 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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 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 $189. Other airlines that can offer you cheap pricing are Frontier, from $298, and Delta, from $307. Spirit Airlines is priced at 48% 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?

    $95 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 $146 and $162, 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: United Airlines (88%), American Airlines (83%), Air Canada (82%).

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

    Looking at all options, your cheapest flight can be booked for $117. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $189 on average our data indicates $805 when flying from Chicago to San Juan.

  • Where are the most common layover locations when flying from Chicago to San Juan?

    Chicago to San Juan flights have a layover in Orlando most of the time.

  • 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 to San Juan flights?

    Of the flights from Chicago to San Juan that have layovers, the fewest flights stop in Charlotte.

  • 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 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$242FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$277FlexibilityNo cancel feeOn-time65%
DeltaCheapest$222Average$432FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$274Average$524FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$404FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$331Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$343Average$479FlexibilityNo cancel feeOn-time63%

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