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O'Hare Intl

$119+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$119
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$297

Good round-trip deal

$339 or less

Good one-way deal

$174 or less
From Puerto Rico to Chicago O'Hare Intl
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One-way flight from Puerto Rico to Chicago O'Hare Intl
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Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 Puerto Rico to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Puerto Rico to Chicago O'Hare Intl.
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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 September 16, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$178
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.
Thu 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$186
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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/13$187
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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Fri 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$192
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/15$206
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.
Thu 10/1611:51 amSJU - ORD
1 stop7h 47mSpirit Airlines
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$208
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/14$209
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 10/33:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/14$214
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.
Thu 11/132:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 11/176:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/13$215
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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Tue 10/286:40 amORD - SJU
1 stop10h 14mMultiple Airlines
Deal found 9/14$217
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/213:32 amBQN - ORD
1 stop17h 12mFrontier
Sat 10/48:00 amORD - BQN
1 stop17h 27mFrontier
Deal found 9/15$286

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 September 16, 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

Thu 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

3:46 pm-11:10 pm

1 stop9h 24m

Chicago O'Hare Intl

Sun 11/9

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/30

5:50 am-12:45 pm

1 stop7h 55m

Chicago O'Hare Intl

Mon 11/3

6:05 am-11:20 pm

2 stops15h 15m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-9:39 pm

1 stop9h 33m

Chicago O'Hare Intl

Wed 10/29

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

Chicago O'Hare Intl

Fri 10/31

5:20 am-4:33 pm

1 stop10h 13m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 11/14

6:40 am-2:45 pm

1 stop10h 05m

Chicago O'Hare Intl

Mon 11/17

3:45 pm-12:35 am

1 stop6h 50m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-10:45 am

1 stop10h 40m

Chicago O'Hare Intl

Tue 11/18

2:20 pm-9:00 pm

Nonstop4h 40m

$257

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 11/13

6:10 am-9:50 pm

2 stops17h 40m

Chicago O'Hare Intl

Mon 11/17

1:45 pm-12:35 am

2 stops8h 50m

$292

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Tue 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 50 results
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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 September 16, 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 September 16, 2025.

The most flights from PR0 to ORD 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 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 September 16, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Puerto Rico to Chicago O'Hare Intl Airport?

    For as low as $223, United Airlines can have you in Chicago O'Hare Intl Airport from Puerto Rico in 7h 20m. The distance between Puerto Rico and Chicago O'Hare Intl Airport is about 2073 mi. This flight may include one or multiple stops.

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

    $143 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on JetBlue and Frontier, with prices starting from $154 and $221, respectively.

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

    The most popular route from Puerto Rico to Chicago O'Hare Intl Airport is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider Aguadilla Borinquen - Chicago O'Hare Intl or Culebra - Chicago O'Hare Intl.

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

    Consider Spirit Airlines (82%), Air Canada (81%) or United Airlines (81%) 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 $106. On average you can expect to pay $515. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $177.

  • 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
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Puerto Rico to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Punta Cana to Midway flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Kingston to O'Hare Intl flights
George Town to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Nassau to Midway flights
Willemstad to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to Midway flights
Roseau to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Aguadilla to Midway flights
Culebra to O'Hare Intl flights
Road Town to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$278FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$390FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$499FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$460FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$481FlexibilityNo cancel feeOn-time71%

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