$89+ Cheap flights from Chicago (CHI) to Puerto Rico
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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Puerto Rico 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.Cheap flight deals from Chicago to Puerto Rico
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Puerto Rico (PR0). 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 diciembre 5, 2024.
Find flight deals from Chicago to Puerto Rico
Cheapest flights from Chicago to Puerto RicoExplore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 5, 2024.
Explore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 5, 2024.
This FlightHub deal was found by Cheapflights users on 12/4. 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 FlightHub deal was found by Cheapflights users on 12/4. 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 12/3. 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 Frontier deal was found by Cheapflights users on 12/4. 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.
This United Airlines deal was found by Cheapflights users on 12/4. 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 12/3. 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 12/3. 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 Delta deal was found by Cheapflights users on 12/3. 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 eDestinos deal was found by Cheapflights users on 12/4. 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 Priceline deal was found by Cheapflights users on 12/4. 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 Southwest deal was found by Cheapflights users on 12/3. 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 United deal was found by Cheapflights users on 12/4. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Chicago to Puerto Rico within your budget
Customize your flight search to find flights from Chicago to Puerto Rico 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 2,924,186 searches. Data last updated diciembre 5, 2024.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 1/14
8:00 am-7:48 pm
1 stop9h 48m
San Juan Luis Munoz Marin Intl
sáb. 1/18
9:26 pm-12:51 am
Nonstop5h 25m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
lun. 2/10
3:16 pm-12:39 am
1 stop7h 23m
San Juan Luis Munoz Marin Intl
mar. 2/11
10:16 am-4:08 pm
1 stop7h 52m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
sáb. 3/1
10:26 am-2:02 am
1 stop13h 36m
San Juan Luis Munoz Marin Intl
mié. 3/5
6:35 am-11:00 pm
1 stop18h 25m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mié. 2/26
7:18 pm-9:35 am
1 stop12h 17m
San Juan Luis Munoz Marin Intl
sáb. 3/1
6:35 am-1:10 pm
1 stop8h 35m
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
dom. 1/19
4:18 pm-2:46 am
1 stop8h 28m
Aguadilla Borinquen
sáb. 1/25
3:51 am-9:52 am
1 stop8h 01m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
dom. 1/26
1:15 pm-10:22 pm
1 stop7h 07m
San Juan Luis Munoz Marin Intl
jue. 1/30
2:05 am-10:44 am
1 stop10h 39m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
dom. 2/2
1:20 pm-12:50 am
2 stops9h 30m
San Juan Luis Munoz Marin Intl
jue. 2/6
5:35 am-2:10 pm
2 stops10h 35m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
jue. 2/27
11:44 am-11:50 pm
1 stop10h 06m
San Juan Luis Munoz Marin Intl
mié. 3/5
3:26 am-12:15 pm
1 stop10h 49m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
mar. 1/28
10:57 am-11:46 pm
1 stop10h 49m
San Juan Luis Munoz Marin Intl
mar. 2/4
7:30 am-4:21 pm
1 stop10h 51m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
lun. 12/16
9:57 pm-5:43 pm
1 stop17h 46m
San Juan Luis Munoz Marin Intl
dom. 1/12
10:09 pm-3:33 pm
2 stops19h 24m
Best time to book a flight from Chicago to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
Travel insights for flights from Chicago to Puerto Rico
Get recent, data-driven insights about flights from Chicago to Puerto Rico including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $254). Flying from Chicago to Puerto Rico in March is currently the most expensive (average of $334). 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 PR?
Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 5, 2024.
When flying from Chicago to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Puerto Rico
Explore weekly flight availability from Chicago to Puerto Rico. 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 diciembre 5, 2024.
The most flights from CHI to PR0 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 Puerto Rico by month
Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Puerto Rico 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 Puerto Rico when rainfall is around 2.2 in.
Temperature in Puerto Rico by month
Plan your trip to Puerto Rico by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Puerto Rico, 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 Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated diciembre 5, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Frontier, United Airlines and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Crew
Entertainment
Boarding
Food
Overall
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.