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$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
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$207
(Mytrip)

One-way from

$108
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$380

Good round-trip deal

$360 or less

Good one-way deal

$187 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 ($35 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 September 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 September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/14. 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.
Sat 10/1111:55 amORD - SJU
2 stops26h 04mSpirit Airlines
Sat 10/189:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 9/14$207
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/249:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Wed 10/293:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/14$208
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:57 amORD - SJU
2 stops20h 59mMultiple Airlines
Tue 10/76:22 amSJU - ORD
1 stop11h 51mMultiple Airlines
Deal found 9/13$209
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/226:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Thu 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Deal found 9/14$210
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/226:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Sat 9/276:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/14$211
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 10/16:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Sat 10/46:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/12$212
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Sat 10/43:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 9/13$213
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 12/36:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Mon 12/82:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/14$215
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:35 amORD - SJU
1 stop11h 09mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/13$216
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sat 10/187:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Tue 10/213:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/14$217
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/282:20 pmORD - SJU
Nonstop4h 40mUnited Airlines
Mon 11/38:10 amSJU - ORD
Nonstop5h 22mUnited Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/279:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Tue 11/49:00 amSJU - ORD
1 stop29h 45mMultiple Airlines
Deal found 9/14$219

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 September 15, 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

Fri 10/31

5:20 am-4:33 pm

1 stop10h 13m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:00 am-5:22 pm

1 stop12h 22m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 11/11

1:36 pm-12:36 am

1 stop9h 00m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-10:45 am

1 stop10h 40m

$256

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 9/28

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Thu 10/2

10:15 am-11:20 pm

2 stops14h 05m

$260

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 9/28

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Fri 10/3

10:15 am-11:59 pm

2 stops14h 44m

$260

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 9/21

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Sun 9/28

10:15 am-7:44 pm

1 stop10h 29m

$278

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 12/5

7:49 pm-9:55 am

1 stop12h 06m

Ponce Mercedita

Mon 12/8

10:50 am-6:44 pm

1 stop9h 54m

$284

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 10/18

8:30 am-2:04 am

1 stop16h 34m

Aguadilla Borinquen

Sat 10/25

2:59 am-7:10 am

1 stop29h 11m

$286

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 11/14

10:18 am-3:04 am

1 stop14h 46m

Aguadilla Borinquen

Sun 11/16

3:59 am-12:16 pm

1 stop10h 17m

$288

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

1:17 pm-11:57 pm

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Mon 10/27

1:05 am-9:02 am

1 stop8h 57m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 45 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, 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 June is currently the most expensive (average of $339). 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 September 15, 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 September 15, 2025.

The most flights from ORD to PR0 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 15, 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
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,015 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,172 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $256, Delta can have you in Puerto Rico from Chicago O'Hare Intl Airport in 9h. 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: Spirit Airlines (79%), American Airlines (77%), Alaska Airlines( 77%).

  • 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 $127. On average you can expect to pay $463. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $168.

  • 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 June is currently the most expensive (average of $339). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
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Midway to Kingston flights
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$315FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$306FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$400FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$418FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$277Average$521FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$350Average$519FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$389Average$481FlexibilityNo cancel feeOn-time63%

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