$69+ 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 2/27. 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.The best prices from San Juan to Chicago are usually found in January or August, booked 51 days in advance, depart on a Thursday or Friday and return on a Tuesday
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 December 9, 2024.
Round-trip from | $149 (Kiwi.com) |
|---|---|
One-way from | $69 (Booking.com) |
Popular in | April |
Cheapest in | January |
Average price | $278 |
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 December 9, 2024.
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 December 9, 2024.
This FlightHub deal was found by Cheapflights users on 12/9. 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 12/8. 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 eDestinos deal was found by Cheapflights users on 12/8. 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 Trip.com deal was found by Cheapflights users on 12/8. 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 American Airlines deal was found by Cheapflights users on 12/8. 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 eDestinos deal was found by Cheapflights users on 12/8. 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 Southwest deal was found by Cheapflights users on 12/9. 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.
This Delta deal was found by Cheapflights users on 12/8. 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.
Find flights from San Juan to Chicago within your budget
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 2,857,848 searches. Data last updated December 9, 2024.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/16
9:26 pm-12:51 am
Nonstop5h 25m
Chicago O'Hare Intl
Sun 1/19
1:44 pm-8:21 pm
Nonstop4h 37m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/16
6:55 pm-8:57 pm
1 stop28h 02m
Chicago O'Hare Intl
Sun 1/19
4:18 pm-10:37 am
1 stop16h 19m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/17
6:00 am-5:53 pm
1 stop13h 53m
Chicago Midway
Mon 1/20
11:33 am-2:19 am
1 stop12h 46m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/16
9:26 pm-12:51 am
Nonstop5h 25m
Chicago O'Hare Intl
Sun 1/19
4:18 pm-2:19 am
1 stop8h 01m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/16
2:05 am-10:44 am
1 stop10h 39m
Chicago O'Hare Intl
Mon 1/20
11:15 am-10:22 pm
1 stop9h 07m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/23
11:45 am-5:53 pm
2 stops32h 08m
Chicago Midway
Mon 1/27
6:15 am-2:30 pm
2 stops30h 15m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/30
6:00 am-11:45 am
1 stop7h 45m
Chicago Midway
Sun 2/2
1:20 pm-12:50 am
2 stops9h 30m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/24
6:15 am-11:59 am
1 stop7h 44m
Chicago Midway
Tue 1/28
6:00 am-5:14 pm
1 stop9h 14m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/27
6:35 am-10:46 pm
1 stop18h 11m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/23
9:26 pm-12:51 am
Nonstop5h 25m
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.
Travel insights for flights from San Juan to Chicago
Get recent, data-driven insights about flights from San Juan to Chicago including ideal travel times, pricing trends, and more.
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 December 6, 2024.
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, September is the cheapest month in which you can book a flight from San Juan to Chicago (average of $232). Flying from San Juan to Chicago in June is currently the most expensive (average of $308). 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 December 9, 2024.
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 41% 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 Monday 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 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 December 9, 2024.
The most flights from PR1 to CHI are scheduled on a Saturday (10 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 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 December 9, 2024.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about American Airlines, Delta and Spirit 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.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.