$104+ 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 9/4. 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
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated June 12, 2025.
Round-trip from | $210 (FlightHub) |
|---|---|
One-way from | $104 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $417 |
Good round-trip deal | $298 or less |
Good one-way deal | $150 or less |
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 June 12, 2025.
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 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 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 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 6/11. 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 United Airlines 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 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 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Chicago to Puerto Rico 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
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 6/18
11:28 am-8:25 am
1 stop19h 57m
Ponce Mercedita
Sun 6/22
9:10 am-8:38 am
1 stop24h 28m
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 7/30
11:28 am-2:01 am
1 stop13h 33m
Aguadilla Borinquen
Sun 8/3
2:59 am-11:31 pm
1 stop21h 32m
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 9/3
12:00 pm-11:09 pm
1 stop10h 09m
Aguadilla Borinquen
Tue 9/9
12:15 am-9:05 am
1 stop9h 50m
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
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Puerto Rico
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 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 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 June 12, 2025.
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 June 12, 2025.
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 June 12, 2025.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Southwest, Delta and United Airlines. 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 Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Puerto Rico
Discover the top 7 airlines that operate flights from Chicago to Puerto Rico. 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$311 | 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$264 | Average$474 | 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% |