$90+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
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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
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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
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 December 30, 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 December 30, 2025.
This JetBlue deal was found by Cheapflights users on 12/29. 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 CheapOair deal was found by Cheapflights users on 12/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 12/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 12/29. 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 Expedia 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 12/28. 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 12/28. 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 American Airlines deal was found by Cheapflights users on 12/27. 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 Frontier deal was found by Cheapflights users on 12/28. 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 Frontier deal was found by Cheapflights users on 12/28. 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 12/28. 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 CheapOair deal was found by Cheapflights users on 12/28. 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 CheapOair 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 12/29. 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.
Find 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 December 30, 2025.
Round-trip from | $162 (SmartFares) |
|---|---|
One-way from | $93 (WAYA) |
Popular in | December |
Cheapest in | February |
Average price | $427 |
Good round-trip deal | $254 or less |
Good one-way deal | $169 or less |
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
Thu 2/26
5:10 am-11:54 am
1 stop8h 44m
Chicago O'Hare Intl
Wed 3/4
12:59 pm-12:29 am
1 stop9h 30m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/19
4:11 pm-10:37 pm
1 stop8h 26m
Chicago Midway
Sat 2/28
8:00 am-2:53 am
1 stop16h 53m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/15
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Mon 1/19
7:45 am-6:05 pm
1 stop8h 20m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 2/7
4:36 pm-7:52 pm
1 stop29h 16m
Chicago Midway
Thu 2/12
7:30 am-2:53 am
1 stop17h 23m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/29
1:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sun 2/1
12:17 pm-6:49 pm
Nonstop4h 32m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 2/25
5:25 pm-2:26 pm
1 stop23h 01m
Chicago Midway
Mon 3/9
9:51 pm-9:57 am
1 stop11h 06m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/6
4:40 pm-11:47 am
2 stops21h 07m
Chicago O'Hare Intl
Mon 2/9
9:23 am-6:58 pm
1 stop7h 35m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 1/14
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Sun 1/18
9:15 am-7:26 pm
1 stop8h 11m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 2/11
11:06 am-7:31 pm
1 stop10h 25m
Chicago O'Hare Intl
Sun 2/15
10:00 am-10:53 pm
1 stop10h 53m
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Wed 1/14
3:48 am-10:32 am
1 stop8h 44m
Chicago Midway
Sun 1/18
6:01 pm-3:03 am
1 stop7h 02m
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 $121). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $175). 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 December 30, 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 53% 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 February 10, 2025.
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. Sunday 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 December 30, 2025.
The most flights from PR0 to CHI are scheduled on a Saturday (13 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (12 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 9% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 169 minutes.
What is the most punctual flight time for Puerto Rico to Chicago 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.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Puerto Rico to Chicago 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 December 30, 2025.
Read reviews from past customers who have flown Delta, 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.
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
Boarding
Comfort
Crew
Overall
Entertainment
Food
Reviews
Jim,Nov 2025
AVL - ATL
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 7 airlines flying from Puerto Rico to Chicago
Discover the top 7 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 December 30, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$228 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$278 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$486 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$277 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$419 | Average$566 | FlexibilityNo cancel fee | On-time63% |