$115+ Cheap flights from Puerto Rico 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Puerto Rico 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.Cheap flight deals from Puerto Rico to Chicago
Keep the following information in mind while searching for Puerto Rico to Chicago flight deals. Data was last updated June 12, 2025.
Round-trip from | $191 (Priceline) |
|---|---|
One-way from | $115 (Frontier) |
Popular in | March |
Cheapest in | January |
Average price | $298 |
Good round-trip deal | $255 or less |
Good one-way deal | $189 or less |
Find flight deals from Puerto Rico to Chicago
Cheapest flights from Puerto Rico to ChicagoExplore the most affordable flight options available from Puerto Rico 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 Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
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 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.
This Trip.com 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 Trip.com 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 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip 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 Puerto Rico 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 Puerto Rico to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Fri 9/26
3:20 am-2:53 pm
1 stop12h 33m
Chicago O'Hare Intl
Sun 10/5
6:10 am-2:25 am
1 stop19h 15m
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
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Wed 9/3
12:15 am-2:50 pm
2 stops15h 35m
Chicago O'Hare Intl
Tue 9/9
7:27 am-11:09 pm
2 stops14h 42m
Best time to book a flight from Puerto Rico to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Puerto Rico with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $245). Flying from Puerto Rico 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 PR to CHI?
Find hourly flight availability from Puerto Rico 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Puerto Rico to Chicago as you normally would.
Weekly flight availability from Puerto Rico to Chicago
Explore weekly flight availability from Puerto Rico 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 PR0 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.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Puerto Rico?
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Alternative routes for Puerto Rico to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico 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$160 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$172 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$438 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$329 | Average$481 | FlexibilityNo cancel fee | On-time71% |