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O'Hare Intl

$108+ Cheap flights from Puerto Rico to O'Hare Intl (ORD)

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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheap flight deals from Puerto Rico to O'Hare Intl

Cheapest flights from Puerto Rico to O'Hare Intl
Explore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sat 7/44:05 pm
SJU
-
ORD
1 stop8h 14m
Frontier
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/5$213
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 9/36:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Tue 9/86:55 am
ORD
-
SJU
2 stops16h 49m
Frontier
Deal found 5/6$214
This eDestinos deal was found by Cheapflights users on 5/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Mon 8/2412:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Deal found 5/9$215
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Tue 8/412:59 am
SJU
-
ORD
Nonstop5h 01m
American Airlines
Mon 8/105:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Deal found 5/8$217
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Wed 9/212:59 am
SJU
-
ORD
Nonstop5h 01m
American Airlines
Mon 9/76:34 am
ORD
-
SJU
1 stop14h 50m
American Airlines
Deal found 5/6$222
This eDestinos deal was found by Cheapflights users on 5/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:05 pm
SJU
-
ORD
1 stop8h 09m
Frontier
Sun 8/2312:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Deal found 5/10$223
This eDestinos deal was found by Cheapflights users on 5/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:24 am
SJU
-
ORD
1 stop14h 50m
Frontier
Mon 8/3112:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Deal found 5/10$224
This Delta deal was found by Cheapflights users on 5/8. 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.
Wed 8/192:59 pm
SJU
-
ORD
1 stop9h 59m
Delta
Mon 8/241:48 pm
ORD
-
SJU
1 stop7h 41m
Delta
Deal found 5/8$226
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Tue 8/412:59 am
SJU
-
ORD
Nonstop5h 01m
American Airlines
Wed 8/125:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Deal found 5/8$228
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Sat 9/512:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Deal found 5/10$231
This eDestinos deal was found by Cheapflights users on 5/8. 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.
Wed 8/56:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Wed 8/128:05 am
ORD
-
SJU
1 stop7h 00m
Frontier
Deal found 5/8$232
This Frontier deal was found by Cheapflights users on 5/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:00 am
BQN
-
ORD
1 stop7h 11m
Frontier
Thu 8/65:13 pm
ORD
-
BQN
1 stop7h 52m
Frontier
Deal found 5/10$321

Find flight deals from Puerto Rico to O'Hare Intl

Keep the following information in mind while searching for Puerto Rico to O'Hare Intl flight deals. Data was last updated May 11, 2026.

Round-trip from

$213
(Kiwi.com)

One-way from

$108
(eDestinos)

Popular in

December

Cheapest in

February

Average price

$327

Good round-trip deal

$295 or less

Good one-way deal

$158 or less
From Puerto Rico to Chicago O'Hare Intl
Search Deals
One-way flight from Puerto Rico to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to O'Hare Intl 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 May 11, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Tue 8/25

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Sat 8/29

2:35 pm-12:33 am

1 stop8h 58m

$379

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 6/6

7:30 am-6:41 pm

1 stop12h 11m

Chicago O'Hare Intl

Sat 6/13

5:30 am-4:46 pm

1 stop10h 16m

$426

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 7/2

3:00 am-11:19 pm

1 stop21h 19m

Chicago O'Hare Intl

Sun 7/12

5:13 pm-2:05 am

1 stop7h 52m

$473

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 6/17

7:20 am-2:29 pm

1 stop8h 09m

Chicago O'Hare Intl

Wed 6/24

2:38 pm-8:34 pm

Nonstop4h 56m

$495

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 6/5

9:00 am-9:54 am

2 stops25h 54m

Chicago O'Hare Intl

Fri 6/12

4:59 pm-2:05 am

1 stop8h 06m

$499

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 6/5

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Tue 6/9

2:38 pm-8:34 pm

Nonstop4h 56m

$523

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/20

7:20 am-2:28 pm

1 stop8h 08m

Chicago O'Hare Intl

Wed 6/10

2:38 pm-8:34 pm

Nonstop4h 56m

$539

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 7/13

3:00 am-11:05 pm

1 stop21h 05m

Chicago O'Hare Intl

Mon 7/20

1:50 pm-11:34 am

2 stops20h 44m

$554

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Tue 6/2

2:59 am-7:29 pm

2 stops17h 30m

Chicago O'Hare Intl

Wed 6/10

4:59 pm-2:05 am

1 stop8h 06m

$567

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/15

3:45 pm-9:55 pm

1 stop7h 10m

Chicago O'Hare Intl

Mon 5/18

6:00 am-11:40 pm

2 stops16h 40m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 44 resultsSorted by cheapest first
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5

Best time to book a flight from Puerto Rico to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

How far ahead should I book a flight from Puerto Rico to Chicago O'Hare Intl Airport?

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 O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Puerto Rico to Chicago O'Hare Intl Airport?

Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $64). Flying from Puerto Rico to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $117). 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 ORD?

Find hourly flight availability from Puerto Rico to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 11, 2026.

A simple way to save on the total cost of your ticket is to fly from Puerto Rico to Chicago O'Hare Intl Airport at noon. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Puerto Rico to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to O'Hare Intl. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Puerto Rico to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon 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 O'Hare Intl Airport

Explore weekly flight availability from Puerto Rico to O'Hare Intl. 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 May 11, 2026.

The most flights from PR0 to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 189 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 Sunday 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.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated May 11, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican Airlines from Puerto Rico to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
9,695 reviews
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
7.2
Good
2,977 reviews
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
11,668 reviews
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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.
Spirit Airlines
6.3
Okay
8,636 reviews
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
2,955 reviews
United Airlines
7.4
Good
9,695 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

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 O'Hare Intl. 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 O'Hare Intl Airport?

    For as low as $379, JetBlue can have you in Chicago O'Hare Intl Airport from Puerto Rico in 9h 38m. The distance between Puerto Rico and Chicago O'Hare Intl Airport is about 2029 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago O'Hare Intl Airport 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 Spirit Airlines, with prices starting from $95 and $97, respectively.

  • What are the most popular routes from Puerto Rico to Chicago O'Hare Intl Airport?

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

  • What are the most reliable airlines from Puerto Rico to Chicago O'Hare Intl Airport?

    Consider Air Canada (89%), United Airlines (89%) or Air New Zealand (89%) when booking your flight. These represent the most reliable airlines when flying from Puerto Rico to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Puerto Rico to Chicago O'Hare Intl Airport?

    The cheapest flight price from Puerto Rico to Chicago O'Hare Intl Airport is $99. On average you can expect to pay $470. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $221.

  • Can I find deals for flights from Puerto Rico to O'Hare Intl that include hotel bookings?

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

  • How can I find direct flights from Puerto Rico to O'Hare Intl?

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

  • Can I find deals for business class flights from Puerto Rico to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Puerto Rico to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $64). Flying from Puerto Rico to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $117). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Rosemont
Schaumburg
Naperville
Gurnee
Delavan
Oakbrook Terrace
Lake Geneva
Benton Harbor
Hoffman Estates
Downers Grove
Des Plaines
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing
Arlington Heights

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Top 7 airlines flying from Puerto Rico to O'Hare Intl

Discover the top 7 airlines that operate flights from Puerto Rico to O'Hare Intl. 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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$418FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$119Average$254FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$120Average$265FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$480FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$438FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$457FlexibilityNo cancel feeOn-time63%

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