$113+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
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 September or August, 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 June 12, 2025.
Round-trip from | $210 (FlightHub) |
|---|---|
One-way from | $113 (SmartFares) |
Popular in | December |
Cheapest in | September |
Average price | $417 |
Find flight deals from Chicago to San Juan
Cheapest flights from Chicago to San JuanExplore 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 June 12, 2025.
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 June 12, 2025.
This FlightHub deal was found by Cheapflights users on 6/10. 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.
This Priceline deal was found by Cheapflights users on 6/10. 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.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
This Priceline deal was found by Cheapflights users on 6/11. 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.
This JetBlue deal was found by Cheapflights users on 6/10. 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.
This United Airlines deal was found by Cheapflights users on 6/10. 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.
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight 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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/18
7:45 am-4:43 pm
1 stop7h 58m
San Juan Luis Munoz Marin Intl
Thu 8/21
3:21 pm-11:54 pm
1 stop9h 33m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/29
2:05 pm-11:54 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Fri 9/5
4:42 pm-11:56 am
1 stop20h 14m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/8
10:43 am-12:05 am
1 stop12h 22m
San Juan Luis Munoz Marin Intl
Tue 7/15
4:43 pm-7:04 am
1 stop15h 21m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 7/12
12:20 pm-12:27 am
1 stop11h 07m
San Juan Luis Munoz Marin Intl
Tue 7/22
4:43 pm-7:04 am
1 stop15h 21m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/1
6:03 pm-11:54 pm
Nonstop4h 51m
San Juan Luis Munoz Marin Intl
Mon 7/7
1:10 am-10:53 am
1 stop10h 43m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/20
6:00 am-2:57 pm
1 stop7h 57m
San Juan Luis Munoz Marin Intl
Sun 8/24
2:59 pm-9:58 pm
1 stop7h 59m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 11/4
10:35 am-11:21 pm
1 stop10h 46m
San Juan Luis Munoz Marin Intl
Wed 11/12
3:30 pm-9:44 pm
1 stop8h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/10
2:55 pm-11:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 7/15
3:45 pm-10:20 pm
1 stop7h 35m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/22
5:05 am-3:30 pm
1 stop9h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 10/17
6:15 am-2:15 pm
1 stop7h 00m
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.
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 June 9, 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 June 12, 2025.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 31% 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 June 12, 2025.
The most flights from CHI to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 June 12, 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.
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Boarding
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
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.
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Alternative routes for Chicago to San Juan
See prices for flight routes from nearby airports that may be better suited for you.
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$281 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$216 | Average$411 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$287 | Average$411 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$338 | Average$514 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$354 | Average$487 | FlexibilityNo cancel fee | On-time63% |