Puerto Rico

$65+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
ene. 26 — feb. 21
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Cheap flight deals from O'Hare Intl to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Puerto Rico (PR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$147
(Priceline)

One-way from

$65
(Frontier)

Good round-trip deal

$295 or less

Good one-way deal

$207 or less
From Chicago O'Hare Intl to Puerto Rico
One-way flight from Chicago O'Hare Intl to Puerto Rico
Price to beat on a round-trip flight from Chicago O'Hare Intl to Puerto Rico.
Price to beat on a one-way flight from Chicago O'Hare Intl to Puerto Rico.

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 enero 21, 2025.

This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/228:44 pmORD - PSE
1 stop13h 09mFrontier
mar. 2/2512:53 pmPSE - ORD
1 stop22h 34mFrontier
Deal found 1/20$147
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
mar. 2/2512:21 pmORD - SJU
Nonstop4h 31mSpirit Airlines
jue. 3/67:00 amSJU - ORD
Nonstop5h 36mSpirit Airlines
Deal found 1/21$160
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
mar. 3/43:14 pmORD - SJU
1 stop16h 35mMultiple Airlines
mié. 3/125:45 pmSJU - ORD
1 stop7h 22mMultiple Airlines
Deal found 1/20$161
This Frontier deal was found by Cheapflights users on 1/21. 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.
vie. 2/217:18 pmORD - SJU
1 stop12h 31mFrontier
mar. 2/259:30 pmSJU - ORD
1 stop13h 57mFrontier
Deal found 1/21$170
This Booking.com deal was found by Cheapflights users on 1/21. 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.
jue. 4/175:07 pmORD - BQN
1 stop7h 50mFrontier
vie. 4/252:47 amBQN - ORD
1 stop21h 52mFrontier
Deal found 1/21$180
This United Airlines deal was found by Cheapflights users on 1/21. 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.
dom. 2/210:35 amORD - SJU
1 stop8h 53mUnited Airlines
mié. 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Deal found 1/21$245
This JetBlue deal was found by Cheapflights users on 1/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/1912:45 pmORD - SJU
1 stop10h 28mJetBlue
jue. 2/275:10 amSJU - ORD
1 stop7h 49mJetBlue
Deal found 1/20$303
This United Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 3/37:30 amORD - BQN
2 stops14h 27mUnited Airlines
jue. 3/61:09 amBQN - ORD
1 stop9h 58mUnited Airlines
Deal found 1/21$448
This JetBlue Airways deal was found by Cheapflights users on 1/21. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/176:20 amORD - BQN
1 stop10h 59mJetBlue
dom. 5/255:45 amBQN - ORD
1 stop7h 32mJetBlue
Deal found 1/21$454
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/68:46 pmORD - CPX
1 stop11h 36mMultiple Airlines
jue. 3/133:05 pmCPX - ORD
2 stops10h 02mMultiple Airlines
Deal found 1/20$553
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/72:20 pmORD - CPX
1 stop25h 01mCape Air
vie. 3/143:05 pmCPX - ORD
1 stop21h 49mCape Air
Deal found 1/20$692
This United deal was found by Cheapflights users on 1/20. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/2110:35 amORD - MAZ
2 stops21h 09mMultiple Airlines
dom. 3/304:13 pmMAZ - ORD
2 stops17h 27mMultiple Airlines
Deal found 1/20$1,098

Find flights from O'Hare Intl to Puerto Rico within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

sáb. 2/22

8:44 pm-11:53 am

1 stop13h 09m

Ponce Mercedita

mar. 2/25

12:53 pm-9:27 am

1 stop22h 34m

$147

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 2/25

12:21 pm-6:52 pm

Nonstop4h 31m

San Juan Luis Munoz Marin Intl

jue. 3/6

7:00 am-10:36 am

Nonstop5h 36m

$160

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 3/4

3:14 pm-9:49 am

1 stop16h 35m

San Juan Luis Munoz Marin Intl

mié. 3/12

5:45 pm-12:07 am

1 stop7h 22m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 2/21

7:18 pm-9:49 am

1 stop12h 31m

San Juan Luis Munoz Marin Intl

mar. 2/25

9:30 pm-9:27 am

1 stop13h 57m

$170

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

jue. 4/17

5:07 pm-1:57 am

1 stop7h 50m

Aguadilla Borinquen

vie. 4/25

9:56 am-11:39 pm

1 stop14h 43m

$180

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 2/2

10:35 am-9:28 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

lun. 12/8

2:05 am-9:37 am

1 stop9h 32m

$245

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 2/19

12:45 pm-1:13 am

1 stop10h 28m

San Juan Luis Munoz Marin Intl

jue. 2/27

5:10 am-10:59 am

1 stop7h 49m

$303

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

lun. 3/3

7:30 am-11:57 pm

2 stops14h 27m

Aguadilla Borinquen

jue. 3/6

1:09 am-9:07 am

1 stop9h 58m

$448

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

sáb. 5/17

6:20 am-6:19 pm

1 stop10h 59m

Aguadilla Borinquen

dom. 5/25

5:45 am-12:17 pm

1 stop7h 32m

$454

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

jue. 3/6

8:46 pm-10:22 am

1 stop11h 36m

Culebra

jue. 3/13

3:05 pm-12:07 am

2 stops10h 02m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 27 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.

Travel insights for flights from O'Hare Intl to Puerto Rico

Get recent, data-driven insights about flights from O'Hare Intl to Puerto Rico including ideal travel times, pricing trends, and more.

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 $254). Flying from Chicago O'Hare Intl Airport to Puerto Rico in March is currently the most expensive (average of $378). 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 enero 21, 2025.

When flying from Chicago O'Hare Intl Airport to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 enero 21, 2025.

The most flights from ORD to PR0 are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 enero 21, 2025.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, United Airlines and Frontier. 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.
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,201 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
8,985 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.0
Good
386 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $65. However, be on the lookout for offers from Spirit Airlines and JetBlue, 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?

  • 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 (83%), Alaska Airlines (83%), Spirit Airlines( 80%).

  • 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 $1,243. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $130.

  • 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 $254). Flying from Chicago O'Hare Intl Airport to Puerto Rico in March is currently the most expensive (average of $378). 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.

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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$156Average$285FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$398FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$497FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$503FlexibilityNo cancel feeOn-time71%
DeltaCheapest$324Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%
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