HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$104+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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

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 March 23, 2026.

This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
-
ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
-
SJU
1 stop26h 39m
Frontier
Deal found 3/20$168
This Expedia deal was found by Cheapflights users on 3/22. 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.
Fri 4/173:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Mon 4/204:58 pm
ORD
-
SJU
1 stop24h 01m
Frontier
Deal found 3/22$176
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
-
ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$178
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Thu 4/163:31 pm
SJU
-
ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
-
SJU
1 stop25h 07m
Frontier
Deal found 3/21$183
This Frontier deal was found by Cheapflights users on 3/20. 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.
Thu 4/163:31 pm
SJU
-
ORD
1 stop9h 13m
Frontier
Thu 4/232:05 pm
ORD
-
SJU
1 stop10h 56m
Frontier
Deal found 3/20$186
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Wed 4/1511:05 am
SJU
-
ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
-
SJU
1 stop25h 07m
Frontier
Deal found 3/21$191
This Frontier deal was found by Cheapflights users on 3/20. 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.
Fri 4/243:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$196
This Gotogate deal was found by Cheapflights users on 3/22. 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 4/176:00 am
SJU
-
ORD
1 stop17h 54m
Frontier
Sun 4/262:20 pm
ORD
-
SJU
1 stop9h 09m
Frontier
Deal found 3/22$198
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:59 am
SJU
-
ORD
1 stop12h 33m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$200
This eDestinos deal was found by Cheapflights users on 3/19. 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.
Thu 4/166:00 am
SJU
-
ORD
1 stop16h 17m
Frontier
Sat 4/188:00 am
ORD
-
SJU
1 stop17h 01m
Frontier
Deal found 3/19$201
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Tue 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sun 4/127:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/18$202
This CheapOair deal was found by Cheapflights users on 3/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 4/135:05 am
ORD
-
SJU
1 stop12h 50m
Spirit Airlines
Deal found 3/18$203

Find 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 March 23, 2026.

Round-trip from

$168
(eDestinos)

One-way from

$104
(Super.com)

Popular in

December

Cheapest in

February

Average price

$359

Good round-trip deal

$325 or less

Good one-way deal

$193 or less
From Puerto Rico to Chicago O'Hare Intl
Search Deals
One-way flight from Puerto Rico to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago O'Hare Intl.
Search Deals

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 March 23, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

Chicago O'Hare Intl

Tue 4/21

10:00 am-3:39 pm

Nonstop4h 39m

$233

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

2:00 pm-8:05 am

1 stop19h 05m

Chicago O'Hare Intl

Tue 4/28

10:00 am-3:39 pm

Nonstop4h 39m

$307

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 9/3

12:46 pm-11:41 pm

1 stop11h 55m

Chicago O'Hare Intl

Mon 9/7

5:14 pm-2:03 am

1 stop7h 49m

$321

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/24

3:37 pm-10:39 pm

2 stops32h 02m

Chicago O'Hare Intl

Mon 4/27

5:50 am-9:54 am

2 stops51h 04m

$321

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/6

3:56 pm-8:15 pm

Nonstop5h 19m

Chicago O'Hare Intl

Wed 5/13

2:38 pm-8:34 pm

Nonstop4h 56m

$327

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/30

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Wed 5/6

2:38 pm-8:34 pm

Nonstop4h 56m

$327

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/15

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Thu 4/23

2:38 pm-8:34 pm

Nonstop4h 56m

$377

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

Tue 4/21

1:19 pm-3:08 pm

1 stop26h 49m

Chicago O'Hare Intl

Tue 4/28

10:00 am-6:43 pm

1 stop7h 43m

$428

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

Mon 4/6

4:36 pm-5:45 am

1 stop14h 09m

Chicago O'Hare Intl

Fri 4/10

11:55 am-9:42 am

2 stops20h 47m

$434

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/24

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Sun 4/26

2:38 pm-8:34 pm

Nonstop4h 56m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 45 resultsSorted by cheapest first
1
2
3
...
5

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, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $113). Flying from Puerto Rico to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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 March 23, 2026.

A simple way to save on the total cost of your ticket is to fly from Puerto Rico to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Puerto Rico to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to O'Hare Intl. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Puerto Rico to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 March 23, 2026.

The most flights from PR0 to ORD are scheduled on a Saturday (16 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 on average).

How often are flights from Puerto Rico to Chicago delayed?

About 8% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 185 minutes.

What is the most punctual flight time for Puerto Rico to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Puerto Rico to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.

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 March 23, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican 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.
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,459 reviews
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.2
Good
2,911 reviews
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,485 reviews
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,533 reviews
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.7
Fair
3,020 reviews
United Airlines
7.4
Good
9,459 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $233, Spirit Airlines can have you in Chicago O'Hare Intl Airport from Puerto Rico in 5h 16m. 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?

    $74 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Spirit Airlines and Frontier, with prices starting from $95 and $103, 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 Mayagüez Eugenio M De Hostos - Chicago O'Hare Intl.

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

    Consider Air Canada (88%), United Airlines (88%) or Air New Zealand (88%) 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 $134. On average you can expect to pay $644. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $202.

  • 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, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $113). Flying from Puerto Rico to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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
Gurnee
Naperville
Lake Geneva
Hoffman Estates
Delavan
Downers Grove
Des Plaines
Elgin
Oak Brook
South Holland
Elk Grove Village
Libertyville
Waukegan
Beloit
Warrenville
Oakbrook Terrace
Bridgeview
Great Lakes

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$122Average$268FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$483FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$446FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$439FlexibilityNo cancel feeOn-time63%

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.
Site
©2026 Cheapflights