Puerto Rico

$113+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 7 — Jul 141
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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 July 2, 2025.

Round-trip from

$207
(Priceline)

One-way from

$113
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$376

Good round-trip deal

$299 or less

Good one-way deal

$190 or less
From Chicago O'Hare Intl to Puerto Rico
One-way flight from Chicago O'Hare Intl to Puerto Rico
Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Chicago O'Hare Intl to Puerto Rico.
Price to beat on a one-way flight from Chicago O'Hare Intl to Puerto Rico.

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 July 2, 2025.

This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:10 amORD - SJU
1 stop8h 01mFrontier
Thu 9/251:11 amSJU - ORD
1 stop11h 52mFrontier
Deal found 6/30$207
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/205:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Sat 8/22:28 pmSJU - ORD
Nonstop5h 19mSpirit Airlines
Deal found 6/30$213
This Priceline deal was found by Cheapflights users on 7/1. 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.
Fri 9/125:10 amORD - SJU
1 stop9h 41mMultiple Airlines
Tue 9/163:19 pmSJU - ORD
1 stop7h 39mMultiple Airlines
Deal found 7/1$216
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/74:37 pmORD - BQN
1 stop8h 24mFrontier
Sun 8/102:59 amBQN - ORD
1 stop22h 06mFrontier
Deal found 6/30$244
This Frontier deal was found by Cheapflights users on 6/30. 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.
Sun 9/78:45 pmORD - PSE
1 stop11h 45mFrontier
Fri 9/2610:15 amPSE - ORD
1 stop10h 25mFrontier
Deal found 6/30$284
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3112:06 pmORD - PSE
1 stop11h 13mJetBlue
Mon 8/41:59 amPSE - ORD
1 stop10h 19mJetBlue
Deal found 6/30$397
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Wed 8/135:16 pmORD - BQN
1 stop7h 45mMultiple Airlines
Sun 8/243:39 amBQN - ORD
2 stops17h 03mMultiple Airlines
Deal found 7/1$430
This Expedia deal was found by Cheapflights users on 6/30. 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.
Wed 7/306:16 amORD - BQN
2 stops14h 17mJetBlue
Mon 8/45:01 amBQN - ORD
2 stops18h 27mJetBlue
Deal found 6/30$458
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 9/37:17 amORD - BQN
2 stops14h 52mUnited Airlines
Tue 9/912:15 amBQN - ORD
1 stop10h 23mUnited Airlines
Deal found 7/1$474
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Wed 7/166:23 pmORD - MAZ
1 stop13h 51mMultiple Airlines
Sun 7/202:00 pmMAZ - ORD
2 stops19h 55mMultiple Airlines
Deal found 7/1$483
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/911:28 amORD - PSE
1 stop19h 58mMultiple Airlines
Mon 7/149:16 amPSE - ORD
2 stops15h 37mMultiple Airlines
Deal found 6/30$508
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Thu 7/176:23 pmORD - CPX
1 stop12h 36mMultiple Airlines
Mon 7/213:05 pmCPX - ORD
2 stops18h 50mMultiple Airlines
Deal found 7/2$519

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 July 2, 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

Mon 9/8

5:10 am-2:11 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Thu 9/25

1:11 am-12:03 pm

1 stop11h 52m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 7/20

5:05 am-9:09 pm

1 stop15h 04m

San Juan Luis Munoz Marin Intl

Sat 8/2

2:28 pm-6:47 pm

Nonstop5h 19m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/12

5:10 am-3:51 pm

1 stop9h 41m

San Juan Luis Munoz Marin Intl

Tue 9/16

3:19 pm-9:58 pm

1 stop7h 39m

$216

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 8/7

4:37 pm-2:01 am

1 stop8h 24m

Aguadilla Borinquen

Sun 8/10

2:59 am-12:05 am

1 stop22h 06m

$244

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 9/7

8:45 pm-9:30 am

1 stop11h 45m

Ponce Mercedita

Fri 9/26

10:15 am-7:40 pm

1 stop10h 25m

$284

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 7/31

12:06 pm-12:19 am

1 stop11h 13m

Ponce Mercedita

Mon 8/4

1:59 am-11:18 am

1 stop10h 19m

$397

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Wed 8/13

5:16 pm-2:01 am

1 stop7h 45m

Aguadilla Borinquen

Sun 8/24

3:39 am-7:42 pm

2 stops17h 03m

$430

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Wed 7/30

6:16 am-9:33 pm

2 stops14h 17m

Aguadilla Borinquen

Mon 8/4

5:01 am-10:28 pm

2 stops18h 27m

$458

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Wed 9/3

7:17 am-11:09 pm

2 stops14h 52m

Aguadilla Borinquen

Tue 9/9

12:15 am-9:38 am

1 stop10h 23m

$474

ChicagoMayagüez

ORD - MAZ

ORDMAZ

Chicago O'Hare Intl

Wed 7/16

6:23 pm-9:14 am

1 stop13h 51m

Mayagüez Eugenio M De Hostos

Sun 7/20

2:00 pm-8:55 am

2 stops19h 55m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 25 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 July 2, 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 July 2, 2025.

The most flights from ORD to PR0 are scheduled on a Wednesday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 July 2, 2025.
Read reviews from past customers who have flown United Airlines, JetBlue, and Spirit 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.

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.0

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.0

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.0

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.0

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.0

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 $113. However, be on the lookout for offers from Frontier and JetBlue, 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?

  • 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 (85%), Alaska Airlines (85%), Air Canada( 83%).

  • 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 $119. On average you can expect to pay $638. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $194.

  • 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.

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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$302FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$294FlexibilityNo cancel feeOn-time65%
DeltaCheapest$212Average$394FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$507FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$418FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$338Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$385Average$486FlexibilityNo cancel feeOn-time63%

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