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Puerto Rico

$108+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheap 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 October 20, 2025.

Round-trip from

$206
(Kiwi.com)

One-way from

$108
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$328 or less

Good one-way deal

$186 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. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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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Find 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 October 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Sat 11/224:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/20$206
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Thu 11/204:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/19$207
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:30 amORD - SJU
1 stop13h 19mFrontier
Sat 11/222:25 amSJU - ORD
1 stop10h 46mFrontier
Deal found 10/18$208
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Tue 11/254:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/19$210
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:40 amORD - SJU
1 stop18h 53mMultiple Airlines
Mon 11/244:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/18$212
This Frontier deal was found by Cheapflights users on 10/19. 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.
Sat 11/156:00 amORD - SJU
1 stop7h 19mFrontier
Fri 1/93:55 amSJU - ORD
1 stop13h 39mFrontier
Deal found 10/19$213
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 10/277:51 pmORD - SJU
1 stop17h 21mMultiple Airlines
Mon 11/39:00 amSJU - ORD
1 stop29h 45mMultiple Airlines
Deal found 10/19$214
This Trip.com deal was found by Cheapflights users on 10/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:40 amORD - SJU
1 stop10h 14mFrontier
Fri 10/319:00 amSJU - ORD
2 stops16h 16mFrontier
Deal found 10/18$215
This Frontier deal was found by Cheapflights users on 10/19. 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.
Tue 10/286:40 amORD - SJU
1 stop10h 14mFrontier
Mon 11/312:29 pmSJU - ORD
2 stops13h 42mFrontier
Deal found 10/19$216
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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.
Tue 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sun 12/79:47 pmSJU - ORD
Nonstop5h 12mSpirit Airlines
Deal found 10/19$217
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:55 amORD - SJU
Nonstop4h 41mSpirit Airlines
Fri 12/129:47 pmSJU - ORD
Nonstop5h 12mSpirit Airlines
Deal found 10/20$218
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/176:40 amORD - SJU
1 stop9h 14mMultiple Airlines
Wed 11/199:00 amSJU - ORD
1 stop11h 34mMultiple Airlines
Deal found 10/19$220

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 October 20, 2025.
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

O'Hare Intl

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

1:45 pm-12:35 am

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Sat 12/6

11:25 am-9:50 pm

1 stop12h 25m

$289

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

1:45 pm-12:35 am

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Tue 12/9

5:45 am-11:10 am

1 stop7h 25m

$289

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Fri 2/13

2:05 am-9:36 am

1 stop9h 31m

$300

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/17

7:00 am-3:25 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Tue 3/24

10:59 am-9:33 pm

1 stop11h 34m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/10

6:05 am-11:20 pm

2 stops15h 15m

San Juan Luis Munoz Marin Intl

Mon 12/15

5:45 am-11:10 am

1 stop7h 25m

$314

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 1/18

2:05 pm-12:27 am

1 stop8h 22m

Aguadilla Borinquen

Tue 1/27

6:15 am-1:10 pm

1 stop8h 55m

$316

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/1

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 3/10

7:35 am-11:57 am

Nonstop5h 22m

$320

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-9:36 am

1 stop9h 31m

$326

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

3:35 pm-12:36 am

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:05 am-9:40 am

1 stop9h 35m

$329

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-10:53 am

1 stop10h 48m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 60 results
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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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $127). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $187). 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 October 20, 2025.

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 55% on your trip compared to booking a flight in the morning.

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 December 16, 2024.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Wednesday afternoons 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.

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 October 20, 2025.

The most flights from ORD to PR0 are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 October 20, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American 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.
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,976 reviews
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,994 reviews
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,026 reviews
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,104 reviews
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,134 reviews
Delta
7.9
Good
7,976 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 $308, Southwest can have you in Puerto Rico from Chicago O'Hare Intl Airport in 7h 25m. 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 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: American Airlines (91%), Alaska Airlines (82%), Spirit Airlines( 78%).

  • 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 $109. On average you can expect to pay $822. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $179.

  • 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $127). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $187). 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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Alternative routes for O'Hare Intl to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to St. John's flights
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Top 7 airlines flying from O'Hare Intl to Puerto Rico

Discover the top 7 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$320FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$305FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$398FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$260Average$418FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$272Average$522FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$524FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$478FlexibilityNo cancel feeOn-time63%

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