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$132+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from Puerto Rico to Chicago

Cheapest flights from Puerto Rico to Chicago
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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 8/2912:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$184
This Frontier deal was found by Cheapflights users on 7/22. 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.
Thu 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$185
This Priceline deal was found by Cheapflights users on 7/23. 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.
Wed 9/27:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 9/512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/23$188
This eDestinos deal was found by Cheapflights users on 7/26. 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.
Thu 8/207:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 8/2212:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$196
This Orbitz deal was found by Cheapflights users on 7/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 9/512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$197
This Frontier deal was found by Cheapflights users on 7/22. 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.
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$198
This Booking.com deal was found by Cheapflights users on 7/22. 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.
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$199
This FlightHub deal was found by Cheapflights users on 7/25. 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.
Thu 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/25$200
This Booking.com deal was found by Cheapflights users on 7/23. 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.
Tue 8/257:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Tue 9/112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/23$204
This Trip.com deal was found by Cheapflights users on 7/26. 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.
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Thu 8/2712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$208
This deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:59 am
SJU
-
ORD
1 stop11h 42m
Frontier
Fri 9/254:49 pm
ORD
-
SJU
1 stop8h 01m
Frontier
Deal found 7/23$211
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/278:55 pm
SJU
-
MDW
1 stop12h 50m
Southwest
Sun 8/308:05 pm
MDW
-
SJU
1 stop12h 05m
Southwest
Deal found 7/22$256

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 July 27, 2026.

Round-trip from

$184
(Kiwi.com)

One-way from

$132
(Orbitz)

Popular in

June

Cheapest in

February

Average price

$340

Good round-trip deal

$319 or less

Good one-way deal

$175 or less
From Puerto Rico to Chicago (CHI)
Search Deals
One-way flight from Puerto Rico to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago (CHI).
Search 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 July 27, 2026.
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

Cheapest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

5:00 am-11:45 am

1 stop7h 45m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

10:00 am-3:35 pm

1 stop6h 35m

Chicago Midway

Wed 9/2

12:20 pm-10:00 pm

1 stop8h 40m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/12

2:50 pm-9:00 pm

1 stop7h 10m

Chicago Midway

Wed 9/16

8:30 am-4:25 pm

1 stop6h 55m

$326

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/9

10:50 pm-8:10 am

1 stop10h 20m

Chicago Midway

Tue 10/13

1:05 pm-11:45 pm

2 stops9h 40m

$346

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

2:35 pm-9:35 pm

1 stop8h 00m

Chicago Midway

Mon 9/21

3:15 pm-11:10 pm

1 stop6h 55m

$346

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

5:00 am-12:25 pm

2 stops8h 25m

Chicago Midway

Wed 9/23

12:40 pm-10:05 pm

2 stops8h 25m

$346

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sat 8/29

2:30 pm-11:44 pm

1 stop10h 14m

Chicago O'Hare Intl

Wed 9/2

2:35 pm-12:33 am

1 stop8h 58m

$362

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/14

8:55 pm-8:55 am

1 stop13h 00m

Chicago Midway

Thu 8/20

1:00 pm-10:50 pm

2 stops8h 50m

$371

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 8/20

2:30 pm-11:44 pm

1 stop10h 14m

Chicago O'Hare Intl

Mon 8/24

2:35 pm-12:33 am

1 stop8h 58m

$372

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 8/19

2:30 pm-11:44 pm

1 stop10h 14m

Chicago O'Hare Intl

Mon 8/24

2:35 pm-12:33 am

1 stop8h 58m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 59 resultsSorted by cheapest first
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6

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $226). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $447). 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 July 27, 2026.

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 30% versus a flight in the afternoon.

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 July 27, 2026.

The most flights from PR0 to CHI are scheduled on a Saturday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

How often are flights from Puerto Rico to Chicago delayed?

About 8% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 185 minutes.

What is the most punctual flight time for Puerto Rico to Chicago flights?

Historically, flights departing at night 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 Tuesday 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 4% of flights being delayed.

How far ahead should I book a flight from Puerto Rico to Chicago?

Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Puerto Rico to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 July 25, 2026.

Travelers seeking maximum savings on their Puerto Rico to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 27, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andJetBlue 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.
United Airlines
7.4
Good
10,042 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
10,042 reviews
United Airlines
7.4
Good
10,042 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,837 reviews
United Airlines
7.4
Good
10,042 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.1
Good
3,026 reviews
United Airlines
7.4
Good
10,042 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.6
Fair
2,754 reviews
United Airlines
7.4
Good
10,042 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • How long is the flight from Puerto Rico to Chicago?

    For as low as $316, Southwest can have you in Chicago from Puerto Rico in 7h 45m. Airlines will cover a distance of 2057 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago one-way?

    $74 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $94 and $128, respectively.

  • What are the most popular routes from Puerto Rico to Chicago?

    The most popular route from Puerto Rico to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Aguadilla Borinquen - Chicago O'Hare Intl.

  • What are the most reliable airlines from Puerto Rico to Chicago?

    No one likes to see their flight delayed. When booking a flight from Puerto Rico to Chicago consider choosing American Airlines (87%), Alaska Airlines (87%) or Air Canada (84%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Puerto Rico to Chicago?

    The cheapest flight price from Puerto Rico to Chicago is $103. On average you can expect to pay $653. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $265.

  • Can I find deals for flights from Puerto Rico to Chicago that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Chicago.

  • Can I find deals for business class flights from Puerto Rico to Chicago?

    Yes. Cheapflights offers flight deals from Puerto Rico to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Puerto Rico to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $226). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $447). 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.

See more FAQs

Traveling to a place near Chicago?

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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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$418FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$128Average$281FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$131Average$204FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$227Average$430FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$266Average$484FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$267Average$479FlexibilityNo cancel feeOn-time69%

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