$117+ Cheap flights from San Juan to Chicago (CHI)
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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from San Juan to Chicago 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 San Juan to Chicago are usually found in January or August, booked 51 days in advance, depart on a Friday or Thursday and return on a Monday
Cheap flight deals from San Juan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). 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 | $191 (Booking.com) |
|---|---|
One-way from | $117 (SmartFares) |
Popular in | March |
Cheapest in | January |
Average price | $298 |
Find flight deals from San Juan to Chicago
Cheapest flights from San Juan to ChicagoExplore the most affordable flight options available from San Juan to Chicago. 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 San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This Booking.com 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 Booking.com 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 6/12. 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 Priceline 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 6/12. 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 Priceline 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 6/12. 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 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 Delta 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 Delta 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 Southwest 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 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 San Juan to Chicago 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 San Juan to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/15
3:50 pm-11:13 pm
1 stop8h 23m
Chicago O'Hare Intl
Tue 7/22
5:05 am-3:30 pm
1 stop9h 25m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/5
3:40 am-2:53 pm
1 stop12h 13m
Chicago O'Hare Intl
Thu 9/11
6:20 am-11:58 pm
1 stop16h 38m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/11
1:11 am-7:20 am
1 stop7h 09m
Chicago Midway
Sun 9/21
8:15 am-11:58 pm
1 stop14h 43m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/26
8:24 pm-8:50 am
1 stop13h 26m
Chicago O'Hare Intl
Thu 8/28
6:35 am-11:54 pm
1 stop16h 19m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 11/12
6:01 am-3:08 pm
1 stop11h 07m
Chicago O'Hare Intl
Wed 11/19
4:05 pm-2:45 am
1 stop8h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/26
6:30 am-1:15 pm
1 stop7h 45m
Chicago Midway
Wed 7/2
11:15 am-7:05 pm
1 stop6h 50m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/11
12:55 pm-9:44 pm
1 stop9h 49m
Chicago Midway
Tue 9/16
10:35 am-10:08 pm
1 stop10h 33m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/10
3:05 pm-7:25 pm
Nonstop5h 20m
Chicago O'Hare Intl
Tue 10/14
4:59 pm-10:50 am
1 stop16h 51m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 7/17
10:14 pm-8:55 am
1 stop11h 41m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 6/24
3:40 am-7:09 am
1 stop28h 29m
Best time to book a flight from San Juan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Juan with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from San Juan to Chicago
How far ahead should I book a flight from San Juan to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Juan to Chicago. Price data was last updated on June 9, 2025.
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 51 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 San Juan to Chicago?
Currently, August is the cheapest month in which you can book a flight from San Juan to Chicago (average of $245). Flying from San Juan to Chicago in March is currently the most expensive (average of $321). 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 SJU to CHI?
Find hourly flight availability from San Juan to Chicago. 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.
When flying from San Juan to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 51% versus a flight at noon.
What is the cheapest day to fly from San Juan to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on December 8, 2024.
Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from San Juan to Chicago
Explore weekly flight availability from San Juan to Chicago. 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 PR1 to CHI are scheduled on a Tuesday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 12, 2025.
To help decide which airline to fly from San Juan to Chicago, 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.
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from San Juan to Chicago. 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 San Juan to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from San Juan to Chicago
Discover the top 6 airlines that operate flights from San Juan to Chicago. 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$135 | Average$264 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$137 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$438 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$329 | Average$481 | FlexibilityNo cancel fee | On-time71% |