O'Hare Intl

$113+ Cheap flights from Puerto Rico to O'Hare Intl (ORD)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
ago. 5 — ago. 121
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Puerto Rico to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Puerto Rico to O'Hare Intl

Keep the following information in mind while searching for Puerto Rico to O'Hare Intl flight deals. Data was last updated julio 31, 2025.

Round-trip from

$221
(FlightHub)

One-way from

$113
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$273 or less

Good one-way deal

$190 or less
From Puerto Rico to Chicago O'Hare Intl
One-way flight from Puerto Rico to Chicago O'Hare Intl
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Puerto Rico to Chicago O'Hare Intl.
Price to beat on a one-way flight from Puerto Rico to Chicago O'Hare Intl.

Find flight deals from Puerto Rico to O'Hare Intl

Cheapest flights from Puerto Rico to O'Hare Intl
Explore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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.
vie. 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
lun. 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31$221
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
mié. 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This Expedia deal was found by Cheapflights users on 7/30. 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.
mié. 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
dom. 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30$242
This Mytrip deal was found by Cheapflights users on 7/30. 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.
mar. 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
sáb. 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30$248
This Frontier deal was found by Cheapflights users on 7/30. 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. 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
vie. 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
This Trip.com deal was found by Cheapflights users on 7/31. 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.
lun. 8/112:59 amBQN - ORD
1 stop8h 15mMultiple Airlines
jue. 8/215:16 pmORD - BQN
1 stop8h 32mMultiple Airlines
Deal found 7/31$284
This Mytrip deal was found by Cheapflights users on 7/31. 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.
vie. 8/155:00 pmMAZ - ORD
2 stops17h 22mMultiple Airlines
mar. 8/196:10 amORD - MAZ
1 stop11h 32mMultiple Airlines
Deal found 7/31$388
This United Airlines deal was found by Cheapflights users on 7/30. 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. 9/1512:15 amBQN - ORD
2 stops19h 19mUnited Airlines
mar. 9/307:15 amORD - BQN
2 stops14h 54mUnited Airlines
Deal found 7/30$422
This Expedia deal was found by Cheapflights users on 7/30. 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.
lun. 11/1010:15 pmBQN - ORD
2 stops22h 50mJetBlue
vie. 11/146:45 amORD - BQN
2 stops12h 34mJetBlue
Deal found 7/30$449
This United Airlines deal was found by Cheapflights users on 7/30. 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.
jue. 8/142:00 pmMAZ - ORD
1 stop7h 15mUnited Airlines
lun. 8/188:49 amORD - MAZ
1 stop6h 38mUnited Airlines
Deal found 7/30$1,956

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to O'Hare Intl 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 julio 31, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago O'Hare Intl Airport that are best for you.

Fly from

Puerto Rico

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

lun. 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$221

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

mié. 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 8/13

3:29 am-3:27 pm

1 stop12h 58m

Chicago O'Hare Intl

dom. 8/17

6:56 am-3:10 pm

1 stop7h 14m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 8/12

3:40 am-10:14 am

1 stop7h 34m

Chicago O'Hare Intl

sáb. 9/13

8:00 am-8:02 am

1 stop23h 02m

$248

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

vie. 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

vie. 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

lun. 8/11

2:59 am-10:14 am

1 stop8h 15m

Chicago O'Hare Intl

jue. 8/21

5:16 pm-2:48 am

1 stop8h 32m

$284

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

vie. 8/15

5:00 pm-9:22 am

2 stops17h 22m

Chicago O'Hare Intl

mar. 8/19

6:10 am-6:42 pm

1 stop11h 32m

$388

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

lun. 9/15

12:15 am-6:34 pm

2 stops19h 19m

Chicago O'Hare Intl

mar. 9/30

7:15 am-11:09 pm

2 stops14h 54m

$422

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

lun. 11/10

10:15 pm-7:05 pm

2 stops22h 50m

Chicago O'Hare Intl

vie. 11/14

6:45 am-9:19 pm

2 stops12h 34m

$449

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

jue. 8/14

2:00 pm-8:15 pm

1 stop7h 15m

Chicago O'Hare Intl

lun. 8/18

8:49 am-4:27 pm

1 stop6h 38m

$1,956

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 results
1
2

Best time to book a flight from Puerto Rico to O'Hare Intl

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

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

Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $245). Flying from Puerto Rico to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 PR to ORD?

Find hourly flight availability from Puerto Rico to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 31, 2025.

When flying from Puerto Rico to Chicago O'Hare Intl Airport, 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 Puerto Rico to Chicago O'Hare Intl Airport

Explore weekly flight availability from Puerto Rico to O'Hare Intl. 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 julio 31, 2025.

The most flights from PR0 to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated julio 31, 2025.
Get a feel of what it's like to fly with United Airlines, JetBlue, and Spirit Airlines from Puerto Rico to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Related info for your journey

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

    $113 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $115 and $196, respectively.

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

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

    Consider Spirit Airlines (99%), Air Canada (92%) or United Airlines (92%) when booking your flight. These represent the most reliable airlines when flying from Puerto Rico to Chicago O'Hare Intl Airport.

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

    The cheapest flight price from Puerto Rico to Chicago O'Hare Intl Airport is $127. On average you can expect to pay $1,810. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $190.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $245). Flying from Puerto Rico to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Elk Grove Village
Racine
Rockford
Tinley Park
Orland Park
Merrillville
Downers Grove
Evanston
Lake Geneva
Gurnee
Joliet

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Discover the top 6 airlines that operate flights from Puerto Rico to O'Hare Intl. 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$272FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$374FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$483FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$431FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$479FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.