$82+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.The best prices from Chicago to San Juan are usually found in January or October, booked 31 days in advance, depart on a Tuesday or Monday and return on a Thursday
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 July 25, 2024.
Popular in | March |
|---|---|
Cheapest in | January |
Round-trip from | $140 (Cheapflightsfares) |
One-way from | $82 (mytrip.com) |
What is the cheapest day to fly round-trip from Chicago to San Juan?
Saturday flights are found to be more expensive to fly from Chicago to San Juan. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San Juan.
How far in advance should I book a flight from Chicago to San Juan?
Travelers have found it’s best to book a flight 32 days in advance to save up to 11% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 32 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to San Juan 1-2 weeks in advance for as low as $256, or $312 for flights within the next 24 hours.
What is the cheapest month to fly from Chicago to San Juan?
The best pricing can be found in the month of January. Prices to San Juan from Chicago average $328. You can even find prices in January for less than $328, as users have found deals to San Juan from as low as $110. The month of March appears to be one of the more expensive times to travel to San Juan from Chicago. Flying in the targeted month can save you up to 55%.
What is the cheapest time of day to fly from CHI to SJU?
It’s typically best to fly out from Chicago to San Juan in the afternoon. Doing so could potentially save you 34% on the flight price compared to flying in the evening, which is usually more expensive.
Cheap Chicago to San Juan flights in July & August 2024
Find cheap flight options from Chicago to San Juan specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in July and August 2024. For more flight deals, be sure to check back very soon.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 FlightHub deal was found by Cheapflights users on 7/24. 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 eDestinos deal was found by Cheapflights users on 7/24. 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.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 FareScan deal was found by Cheapflights users on 7/24. 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 FareScan 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 7/24. 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 FareScan deal was found by Cheapflights users on 7/24. 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 FareScan 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 7/24. 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 FlightHub deal was found by Cheapflights users on 7/24. 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.
Chicago to San Juan 2024 flight deals
Discover exclusive flight deals for travel between Chicago and San Juan in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in July and August 2024. For more flight deals, be sure to check back very soon.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 FlightHub deal was found by Cheapflights users on 7/24. 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 eDestinos deal was found by Cheapflights users on 7/24. 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.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 FareScan deal was found by Cheapflights users on 7/24. 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 FareScan 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 7/24. 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 eDestinos deal was found by Cheapflights users on 7/24. 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.
This FareScan deal was found by Cheapflights users on 7/24. 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 FareScan 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 7/24. 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.
Chicago to San Juan flights leaving soon
Find last-minute flight options from Chicago to San Juan for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Users seeking a last-minute flight from Chicago to San Juan should consider booking one of these fares. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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 Cheapflightsfares deal was found by Cheapflights users on 7/25. 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 FareScan deal was found by Cheapflights users on 7/25. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com 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 7/25. 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 Trip.com deal was found by Cheapflights users on 7/25. 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.
This eDestinos deal was found by Cheapflights users on 7/24. 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.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 7/25. 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.
One-way flights to San Juan from Chicago
Search for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Users in need of a one-way flight from Chicago to San Juan can choose from these deals. Those needing a return flight from Chicago to San Juan can use the search form above.
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FareScan deal was found by Cheapflights users on 7/24. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 7/24. 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.
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FareScan deal was found by Cheapflights users on 7/24. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 2,752,877 searches. Data last updated July 25, 2024.
Fly from
Fly to
Budget
$140 - $324
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/13
1 stop10h 36m
San Juan Luis Munoz Marin Intl
Wed 8/21
1 stop10h 22m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/6
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Thu 8/8
1 stop12h 48m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/13
1 stop10h 36m
San Juan Luis Munoz Marin Intl
Wed 8/14
2 stops18h 17m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/10
1 stop13h 19m
San Juan Luis Munoz Marin Intl
Mon 8/19
1 stop20h 25m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/13
1 stop10h 36m
San Juan Luis Munoz Marin Intl
Mon 8/19
1 stop20h 25m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/6
1 stop14h 16m
San Juan Luis Munoz Marin Intl
Mon 8/19
1 stop20h 25m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 8/23
1 stop20h 51m
San Juan Luis Munoz Marin Intl
Fri 8/30
1 stop7h 38m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 12/3
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Tue 12/10
1 stop10h 48m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 12/7
1 stop6h 58m
San Juan Luis Munoz Marin Intl
Wed 12/11
1 stop11h 44m
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 July 23, 2024.
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 31 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 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 July 21, 2024.
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.
Temperature and rainfall in San Juan by month
Plan your trip to San Juan by taking into account the average temperature and rainfall totals by month.
SJU Temperature | 77 - 82.4 °F |
|---|
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 July 25, 2024.
To help decide which airline to fly from Chicago to San Juan, see what other customers have to say about Spirit Airlines, Frontier and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
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 JuanSee prices for flight routes from nearby airports that may be better suited for you.
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 2,752,877 searches. Data last updated July 25, 2024.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$260 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$311 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$137 | Average$393 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$150 | Average$578 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$514 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$479 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$321 | Average$493 | FlexibilityNo cancel fee | On-time71% |
Search flights from Chicago to San Juan by cabin class
Find flights from Chicago to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to San Juan
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 July 25, 2024.
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 100%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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 July 25, 2024.
| Sunday | 5daily flights |
|---|---|
| Monday | 7daily flights |
| Tuesday | 7daily flights |
| Wednesday | 7daily flights |
| Thursday | 7daily flights |
| Friday | 7daily flights |
| Saturday | 10daily flights |