$108+ 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 12/21. 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 November 21, 2025.
Round-trip from | $187 (Cheapflightsfares) |
|---|---|
One-way from | $108 (Cheapflightsfares) |
Popular in | December |
Cheapest in | January |
Average price | $341 |
Good round-trip deal | $339 or less |
Good one-way deal | $179 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 November 21, 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 November 21, 2025.
This JetBlue deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 11/19. 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 11/18. 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 Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com 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 11/20. 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 Trip.com deal was found by Cheapflights users on 11/19. 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 Trip.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com 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 11/19. 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 Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
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
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sa 3/7
5:10 am-11:58 am
1 stop8h 48m
Chicago O'Hare Intl
Do 3/12
10:56 am-11:23 pm
1 stop11h 27m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Do 1/29
1:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
So 2/1
12:22 pm-6:54 pm
Nonstop4h 32m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Do 12/11
10:42 am-9:53 pm
1 stop13h 11m
Chicago Midway
Mo 12/15
3:52 pm-11:25 pm
1 stop29h 33m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fr 12/12
3:40 pm-9:52 pm
1 stop8h 12m
Chicago O'Hare Intl
Fr 12/19
6:45 am-6:49 pm
1 stop10h 04m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Do 2/19
4:11 pm-11:25 pm
1 stop9h 14m
Chicago Midway
So 2/22
8:56 pm-9:55 am
1 stop10h 59m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Do 12/4
3:55 am-10:39 pm
1 stop20h 44m
Chicago Midway
Mo 12/8
6:15 am-3:11 pm
1 stop6h 56m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mi 5/6
3:30 am-2:20 pm
1 stop11h 50m
Chicago O'Hare Intl
Di 5/12
3:15 pm-12:59 am
1 stop8h 44m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mi 1/21
6:10 am-11:35 am
1 stop7h 25m
Chicago Midway
Di 1/27
9:50 am-11:10 pm
1 stop11h 20m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fr 1/16
2:15 pm-10:07 pm
1 stop9h 52m
Chicago Midway
Mo 1/19
12:48 pm-11:45 pm
1 stop8h 57m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fr 1/23
6:10 am-1:55 pm
2 stops9h 45m
Chicago Midway
Mo 1/26
1:15 pm-11:10 pm
1 stop7h 55m
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, January is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $117). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $193). 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 November 21, 2025.
When flying from Puerto Rico 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 15% versus a flight in the afternoon.
What is the cheapest day to fly from Puerto Rico to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Chicago. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Puerto Rico to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 November 21, 2025.
The most flights from PR0 to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).
How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?
About 9% of weekly flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced delays in the past year, with the average delay time being 169 minutes.
What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.
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 November 21, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Puerto Rico to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Food
Comfort
Entertainment
Boarding
Overall
Crew
Reviews
Mike,Aug 2025
OKC - AUS
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.
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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 November 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$279 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$139 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$487 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$485 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$334 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$516 | FlexibilityNo cancel fee | On-time63% |