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$91+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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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 December 22, 2024.

Round-trip from

$147
(Mytrip)

One-way from

$91
(FlightHub)
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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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 December 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:35 pmORD - SJU
1 stop15h 44mSpirit Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/21$244
This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/304:41 pmORD - SJU
1 stop11h 49mMultiple Airlines
Sat 1/189:26 pmSJU - ORD
Nonstop5h 25mMultiple Airlines
Deal found 12/20$310
This Frontier deal was found by Cheapflights users on 12/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/304:41 pmORD - SJU
1 stop11h 49mFrontier
Sat 1/189:15 pmSJU - ORD
1 stop14h 37mFrontier
Deal found 12/20$318
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/236:37 amORD - SJU
1 stop11h 41mAmerican Airlines
Tue 12/247:05 amSJU - ORD
2 stops9h 07mAmerican Airlines
Deal found 12/20$418
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2710:59 amORD - BQN
1 stop13h 44mFrontier
Sun 12/293:43 amBQN - ORD
1 stop8h 11mFrontier
Deal found 12/21$489
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/302:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Mon 1/132:05 amSJU - ORD
1 stop10h 39mUnited Airlines
Deal found 12/21$503
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/231:55 pmORD - BQN
1 stop8h 02mUnited Airlines
Wed 12/251:09 amBQN - ORD
2 stops19h 09mUnited Airlines
Deal found 12/21$972
This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/273:31 pmORD - BQN
1 stop9h 12mMultiple Airlines
Sun 12/293:43 amBQN - ORD
2 stops17h 36mMultiple Airlines
Deal found 12/21$1,346

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/31

10:59 am-2:19 am

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Sat 2/8

9:26 pm-12:51 am

Nonstop5h 25m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/12

4:11 pm-2:21 am

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Sat 1/18

9:15 pm-9:52 am

1 stop14h 37m

$168

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 1/19

4:18 pm-2:46 am

1 stop8h 28m

Aguadilla Borinquen

Sat 1/25

3:51 am-9:52 am

1 stop8h 01m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/14

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Sat 1/25

9:26 pm-12:51 am

Nonstop5h 25m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/26

6:44 pm-11:00 am

1 stop15h 16m

San Juan Luis Munoz Marin Intl

Tue 4/29

5:55 pm-11:57 pm

1 stop7h 02m

$234

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/9

5:50 pm-6:12 am

1 stop10h 22m

San Juan Luis Munoz Marin Intl

Thu 2/13

2:05 am-9:05 am

1 stop9h 00m

$258

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/3

9:05 am-7:56 pm

1 stop8h 51m

San Juan Luis Munoz Marin Intl

Mon 2/10

6:05 am-3:43 pm

1 stop11h 38m

$302

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/24

7:00 am-9:35 pm

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Fri 2/28

6:05 am-2:00 pm

1 stop9h 55m

$304

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 2/9

1:44 pm-8:15 am

1 stop16h 31m

Culebra

Fri 2/14

10:00 am-11:54 pm

1 stop15h 54m

$407

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 5/1

4:21 pm-8:57 am

1 stop15h 36m

Ponce Mercedita

Mon 5/12

9:57 am-11:38 pm

1 stop14h 41m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 23 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 $380). 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 December 22, 2024.

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 December 22, 2024.

The most flights from ORD to PR0 are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 December 22, 2024.
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.
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

JetBlue
7.4
Good
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

Spirit Airlines
6.3
Okay
8,111 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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 Spirit Airlines, with whom users have recently found tickets for as low as $91. However, be on the lookout for offers from United Airlines and Frontier, 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 - Culebra.

  • 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 (100%), Alaska Airlines (100%), Air Canada( 85%).

  • 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 $64. On average you can expect to pay $687. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $126.

  • 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 $380). 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.

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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 Gregory Town flights
Midway to Georgetown flights
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Midway to Santiago de los Caballeros flights

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$287FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$295FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$495FlexibilityNo cancel feeOn-time69%
DeltaCheapest$307Average$423FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$498FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%
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