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$114+ Cheap flights from O'Hare Intl (ORD) to Puerto Rico

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 18 — Jul 251
Sat 7/18
Sat 7/25
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Puerto Rico

Cheapest flights from O'Hare Intl to Puerto Rico
Explore the most affordable flight options available from O'Hare Intl to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.

This United Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 8/265:30 am
ORD
-
SJU
1 stop9h 12m
United Airlines
Sun 8/303:56 pm
SJU
-
ORD
Nonstop5h 09m
United Airlines
Deal found 6/15$254
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 8/226:40 am
ORD
-
SJU
1 stop8h 58m
Delta
Mon 8/317:00 am
SJU
-
ORD
1 stop8h 09m
Delta
Deal found 6/16$256
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Thu 8/275:20 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
-
ORD
1 stop11h 57m
American Airlines
Deal found 6/15$257
This Expedia deal was found by Cheapflights users on 6/13. 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.
Wed 8/2612:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Sat 8/296:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/13$259
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/15$260
This Frontier deal was found by Cheapflights users on 6/17. 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.
Mon 8/1712:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 8/316:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/17$262
This Frontier deal was found by Cheapflights users on 6/16. 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 8/1912:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 8/246:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/16$263
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Mon 8/1712:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/15$265
This American Airlines deal was found by Cheapflights users on 6/15. 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 8/268:54 am
ORD
-
SJU
1 stop14h 05m
American Airlines
Thu 9/32:33 pm
SJU
-
ORD
1 stop10h 11m
American Airlines
Deal found 6/15$266
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Tue 8/2512:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Sun 8/306:16 pm
SJU
-
ORD
1 stop29h 58m
Frontier
Deal found 6/15$267
This JetBlue deal was found by Cheapflights users on 6/13. 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.
Tue 7/212:35 pm
ORD
-
PSE
1 stop8h 24m
JetBlue
Tue 7/285:01 am
PSE
-
ORD
1 stop9h 38m
JetBlue
Deal found 6/13$347
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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.
Wed 8/122:35 pm
ORD
-
BQN
1 stop8h 58m
JetBlue
Wed 8/195:01 am
BQN
-
ORD
1 stop9h 38m
JetBlue
Deal found 6/15$352

Find flight deals from O'Hare Intl to Puerto Rico

Keep the following information in mind while searching for O'Hare Intl to Puerto Rico flight deals. Data was last updated June 18, 2026.

Round-trip from

$254
(United Airlines)

One-way from

$114
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$455

Good round-trip deal

$396 or less

Good one-way deal

$205 or less
From Chicago O'Hare Intl to Puerto Rico
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One-way flight from Chicago O'Hare Intl to Puerto Rico
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Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2026
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Puerto Rico.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Puerto Rico.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Puerto Rico 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 18, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/17

6:40 am-4:38 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Sat 8/29

7:00 am-4:51 pm

1 stop10h 51m

$306
Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/8

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 8/11

7:20 am-2:30 pm

1 stop8h 10m

$353

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 7/17

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Tue 7/21

5:01 am-1:39 pm

1 stop9h 38m

$358

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 7/17

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Wed 7/22

5:01 am-1:39 pm

1 stop9h 38m

$358

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 7/4

6:40 pm-5:29 am

1 stop9h 49m

San Juan Luis Munoz Marin Intl

Fri 7/10

1:00 am-7:42 am

1 stop7h 42m

$358

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Tue 7/14

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Tue 7/21

5:01 am-1:39 pm

1 stop9h 38m

$361

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Tue 7/21

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Thu 7/30

5:01 am-1:39 pm

1 stop9h 38m

$363

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 8/21

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Tue 8/25

5:01 am-1:39 pm

1 stop9h 38m

$373

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 7/25

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Tue 7/28

5:01 am-1:39 pm

1 stop9h 38m

$373

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 8/7

8:02 pm-5:29 am

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Tue 8/11

7:20 am-2:30 pm

1 stop8h 10m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from O'Hare Intl to Puerto Rico

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $113). Flying from Chicago O'Hare Intl Airport to Puerto Rico in August is currently the most expensive (average of $887). 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 ORD to PR?

Find hourly flight availability from O'Hare Intl to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 18, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Puerto Rico in the evening. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the morning.

Weekly flight availability from Chicago O'Hare Intl Airport to Puerto Rico

Explore weekly flight availability from O'Hare Intl to Puerto Rico. 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 18, 2026.

The most flights from ORD to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

How often are flights from Chicago to Puerto Rico delayed?

About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Chicago to Puerto Rico 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 Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Puerto Rico flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.

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

The price you pay for your flight from Chicago O'Hare Intl Airport to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Puerto Rico. Price data was last updated on June 13, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated June 18, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Puerto Rico. 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.
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,235 reviews
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
United Airlines
7.4
Good
9,857 reviews
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
American Airlines
7.1
Good
11,679 reviews
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
JetBlue
7.1
Good
2,983 reviews
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Frontier
5.6
Fair
2,880 reviews
Southwest
7.9
Good
4,235 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Puerto Rico. 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 Chicago O'Hare Intl Airport to Puerto Rico?

    For as low as $353, Delta can have you in Puerto Rico from Chicago O'Hare Intl Airport in 4h 56m. The distance between Chicago O'Hare Intl Airport and Puerto Rico is about 2073 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Puerto Rico one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $75. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Chicago O'Hare Intl Airport to Puerto Rico for a low price.

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

    The most popular flight routes from Chicago O'Hare Intl Airport to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Aguadilla Borinquen and Chicago O'Hare Intl - Ponce Mercedita.

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

    Before booking your flight to Puerto Rico from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: Air Canada (86%), United Airlines (86%), Air New Zealand( 86%).

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

    The cheapest flight price from Chicago O'Hare Intl Airport to Puerto Rico is $130. On average you can expect to pay $711. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $187.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $113). Flying from Chicago O'Hare Intl Airport to Puerto Rico in August is currently the most expensive (average of $887). 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

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Top 6 airlines flying from O'Hare Intl to Puerto Rico

Discover the top 6 airlines that operate flights from O'Hare Intl to Puerto Rico. 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 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$143Average$366FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$146Average$326FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$261Average$524FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$303Average$503FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$376Average$482FlexibilityNo cancel feeOn-time63%

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