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$83+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Chicago to San Juan are usually found in April or August, booked 38 days in advance, depart on a Tuesday or Wednesday 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 febrero 20, 2025.

Round-trip from

$168
(Booking.com)

One-way from

$83
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$372
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. 15% potential increase in price ($69 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 February 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 febrero 20, 2025.

This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/105:05 amORD - SJU
1 stop18h 10mMultiple Airlines
sáb. 3/156:00 amSJU - ORD
Nonstop5h 36mMultiple Airlines
Deal found 2/20$168
This Mytrip deal was found by Cheapflights users on 2/19. 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.
mié. 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
mar. 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/1410:00 amORD - SJU
Nonstop4h 51mSpirit Airlines
vie. 5/304:46 pmSJU - ORD
Nonstop5h 04mSpirit Airlines
Deal found 2/20$169
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
jue. 3/135:45 amSJU - ORD
1 stop14h 09mFrontier
Deal found 2/20$171
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/1011:30 amORD - SJU
1 stop7h 40mDelta
mié. 3/192:42 pmSJU - ORD
1 stop7h 16mDelta
Deal found 2/20$271
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
mar. 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/286:35 pmORD - SJU
1 stop9h 37mUnited Airlines
sáb. 3/12:05 amSJU - ORD
1 stop9h 00mUnited Airlines
Deal found 2/20$296
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/611:00 amMDW - SJU
1 stop11h 30mSouthwest
mar. 3/115:35 amSJU - MDW
2 stops8h 45mSouthwest
Deal found 2/20$378

Find flights from Chicago to San Juan within your budget

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 febrero 20, 2025.

Fly from

Chicago

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 3/10

5:05 am-12:15 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

sáb. 3/15

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mié. 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

mar. 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 5/14

10:00 am-3:51 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

vie. 5/30

4:46 pm-8:50 pm

Nonstop5h 04m

$169

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 3/8

1:30 pm-1:40 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

jue. 3/13

5:45 am-6:54 pm

1 stop14h 09m

$171

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 3/10

11:30 am-8:10 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mié. 3/19

2:42 pm-8:58 pm

1 stop7h 16m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 3/11

12:51 pm-11:07 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

mar. 3/18

12:54 pm-10:23 pm

1 stop10h 29m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 3/6

11:00 am-12:30 am

1 stop11h 30m

San Juan Luis Munoz Marin Intl

mar. 3/11

5:35 am-1:20 pm

2 stops8h 45m

$378

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 3/29

7:45 pm-2:51 pm

1 stop18h 06m

$83

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 4/25

4:30 pm-12:08 am

1 stop6h 38m

$84

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 5/5

6:15 am-2:47 pm

1 stop7h 32m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 19 results
1
2

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.

Travel insights for flights from Chicago to San Juan

Get recent, data-driven insights about flights from Chicago to San Juan including ideal travel times, pricing trends, and more.

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 38 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 March is currently the most expensive (average of $363). 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 febrero 20, 2025.

It’s typically best to fly out from Chicago to San Juan at noon. Doing so could potentially save you 14% 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 at noon when fares are most often at their lowest. Thursday 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 febrero 20, 2025.

The most flights from CHI to PR1 are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 febrero 20, 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
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Sun Country Air
7.0
Good
374 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $168. Other airlines that can offer you cheap pricing are Spirit Airlines, from $169, and Delta, from $271. Frontier is priced at 54% 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?

    $83 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 United Airlines, with prices starting from $84 and $136, 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 (85%), Alaska Airlines (85%), Spirit Airlines (81%).

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

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $126 on average our data indicates $792 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. Charlotte follows Orlando in terms of the most common layover location on Chicago to San Juan flights.

  • 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 $27 per day.

  • What are some popular points of interest to see during a layover in Charlotte?

    Carowind, Mint Museum Uptown, and North Carolina Blumenthal Performing Arts Center are the most popular attractions in Charlotte if you're in need of something to do during your layover. Carowind, Mint Museum Uptown, and North Carolina Blumenthal Performing Arts Center can be visited by traveling about 8.2 mi, 5.4 mi, and 5.8 mi respectively from Charlotte Douglas. Travelers can rent a car at Charlotte Douglas for an average daily rate of $44 to make sightseeing during their layover a little easier.

  • 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 Atlanta.

  • 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 March is currently the most expensive (average of $363). 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$276FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$151Average$274FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$258Average$522FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$412FlexibilityNo cancel feeOn-time62%
DeltaCheapest$293Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$323Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$482FlexibilityNo cancel feeOn-time63%
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