HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$65+ Cheap flights from Chicago (CHI) 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
ene. 28 — feb. 41
mar. 1/28
mar. 2/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Puerto Rico 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 Chicago to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Puerto Rico (PR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 23, 2025.

Round-trip from

$161
(Kiwi.com)

One-way from

$65
(Frontier)

Good round-trip deal

$295 or less

Good one-way deal

$207 or less
From Chicago (CHI) to Puerto Rico
Search Deals
One-way flight from Chicago (CHI) to Puerto Rico
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Puerto Rico.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Puerto Rico.
Search Deals

Find flight deals from Chicago to Puerto Rico

Cheapest flights from Chicago to Puerto Rico
Explore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 23, 2025.

This FlightHub deal was found by Cheapflights users on 1/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/228:44 pmORD - PSE
1 stop13h 09mFrontier
mar. 2/2512:53 pmPSE - ORD
1 stop22h 34mFrontier
Deal found 1/22$147
This Cheapflightsfares deal was found by Cheapflights users on 1/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/2712:25 pmORD - SJU
1 stop10h 34mSpirit Airlines
jue. 2/69:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 1/22$160
This Booking.com deal was found by Cheapflights users on 1/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/110:26 amMDW - SJU
1 stop13h 36mFrontier
mié. 3/56:35 amSJU - MDW
1 stop18h 25mFrontier
Deal found 1/22$160
This CheapOair deal was found by Cheapflights users on 1/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/228:44 pmORD - SJU
1 stop23h 52mMultiple Airlines
jue. 2/279:34 pmSJU - ORD
1 stop15h 06mMultiple Airlines
Deal found 1/22$162
This Frontier deal was found by Cheapflights users on 1/23. 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.
dom. 2/168:14 amORD - SJU
1 stop12h 22mFrontier
mié. 2/199:30 pmSJU - ORD
1 stop11h 39mFrontier
Deal found 1/23$170
This Priceline deal was found by Cheapflights users on 1/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/175:07 pmORD - BQN
1 stop7h 50mFrontier
vie. 4/259:56 amBQN - ORD
1 stop14h 43mFrontier
Deal found 1/21$180
This Southwest deal was found by Cheapflights users on 1/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
vie. 2/74:30 pmSJU - MDW
1 stop7h 30mSouthwest
Deal found 1/22$285
This JetBlue Airways deal was found by Cheapflights users on 1/23. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/51:24 pmORD - SJU
1 stop9h 43mJetBlue
mié. 4/95:05 amSJU - ORD
1 stop8h 22mJetBlue
Deal found 1/23$303
This Delta deal was found by Cheapflights users on 1/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/412:44 pmMDW - SJU
1 stop9h 02mDelta
vie. 2/72:00 pmSJU - MDW
1 stop10h 20mDelta
Deal found 1/22$325
This Trip.com deal was found by Cheapflights users on 1/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/112:25 pmORD - BQN
1 stop12h 21mMultiple Airlines
dom. 2/23:51 amBQN - ORD
1 stop14h 32mMultiple Airlines
Deal found 1/22$348
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/112:55 pmORD - BQN
1 stop9h 02mUnited Airlines
mar. 3/41:09 amBQN - ORD
1 stop10h 37mUnited Airlines
Deal found 1/21$430
This JetBlue Airways deal was found by Cheapflights users on 1/23. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/176:20 amORD - BQN
1 stop10h 59mJetBlue
dom. 5/255:45 amBQN - ORD
1 stop7h 32mJetBlue
Deal found 1/23$454

Find flights from Chicago to Puerto Rico within your budget

Customize your flight search to find flights from Chicago 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 enero 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

sáb. 2/22

8:44 pm-11:53 am

1 stop13h 09m

Ponce Mercedita

mar. 2/25

12:53 pm-9:27 am

1 stop22h 34m

$147

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 1/27

12:25 pm-12:59 am

1 stop10h 34m

San Juan Luis Munoz Marin Intl

jue. 2/6

9:26 pm-12:51 am

Nonstop5h 25m

$160

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

sáb. 3/1

10:26 am-2:02 am

1 stop13h 36m

San Juan Luis Munoz Marin Intl

mié. 3/5

6:35 am-11:00 pm

1 stop18h 25m

$160

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 2/22

8:44 pm-10:36 pm

1 stop23h 52m

San Juan Luis Munoz Marin Intl

vie. 2/28

9:34 pm-10:40 am

1 stop15h 06m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 2/26

7:18 pm-12:46 am

1 stop27h 28m

San Juan Luis Munoz Marin Intl

lun. 3/3

3:49 am-10:38 pm

1 stop20h 49m

$180

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

jue. 4/17

5:07 pm-1:57 am

1 stop7h 50m

Aguadilla Borinquen

vie. 4/25

9:56 am-11:39 pm

1 stop14h 43m

$180

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

dom. 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

vie. 2/7

4:30 pm-10:00 pm

1 stop7h 30m

$285

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 4/5

1:24 pm-12:07 am

1 stop9h 43m

San Juan Luis Munoz Marin Intl

mié. 4/9

5:05 am-12:27 pm

1 stop8h 22m

$303

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 2/4

6:00 am-5:14 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

vie. 2/7

7:30 am-4:20 pm

1 stop10h 50m

$325

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

sáb. 2/1

12:25 pm-2:46 am

1 stop12h 21m

Aguadilla Borinquen

dom. 2/2

3:51 am-4:23 pm

1 stop14h 32m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 30 results
1
2
3

Best time to book a flight from Chicago to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago 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.

Travel insights for flights from Chicago to Puerto Rico

Get recent, data-driven insights about flights from Chicago to Puerto Rico including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $254). Flying from Chicago to Puerto Rico in March is currently the most expensive (average of $375). 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 CHI to PR?

Find hourly flight availability from Chicago 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 enero 23, 2025.

When flying from Chicago 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 to Puerto Rico

Explore weekly flight availability from Chicago 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 enero 23, 2025.

The most flights from CHI to PR0 are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 enero 23, 2025.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, United Airlines and Frontier. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,647 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,186 reviews
Southwest
8.1
Very good
4,647 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,971 reviews
Southwest
8.1
Very good
4,647 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Puerto Rico one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $65. Spirit Airlines flights start at $80 while deals on JetBlue start at $157 one-way.

  • What are the most popular routes from Chicago to Puerto Rico?

    The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Aguadilla Borinquen.

  • What are the most reliable airlines from Chicago to Puerto Rico?

    Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (83%), Alaska Airlines (83%), Spirit Airlines( 80%).

  • What are the cheapest flights from Chicago to Puerto Rico?

    On average you can expect to pay $1,243 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $109 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $130.

  • Can I find deals for flights from Chicago to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Chicago to Puerto Rico?

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

  • Can I find deals for business class flights from Chicago to Puerto Rico?

    Yes. Cheapflights offers flight deals from Chicago 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 to Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $254). Flying from Chicago to Puerto Rico in March is currently the most expensive (average of $375). 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

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.

Alternative routes for Chicago 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
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Nassau flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
Midway to Montego Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
Midway to Oranjestad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
Midway to Castries flights
Midway to Simpson Bay flights
Midway to Santo Domingo flights
St. Louis to Montego Bay flights
Midway to George Town flights
O'Hare Intl to Puerto Plata flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Castries flights
St. Louis to Nassau flights
O'Hare Intl to St. John's flights
St. Louis to Oranjestad flights
St. Louis to Castries flights
St. Louis to George Town flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kingston flights
St. Louis to Providenciales flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to St. George's flights
O'Hare Intl to Basseterre flights
St. Louis to Simpson Bay flights
St. Louis to Christiansted flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Road Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Kralendijk flights

Top 7 airlines flying from Chicago to Puerto Rico

Discover the top 7 airlines that operate flights from Chicago 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 enero 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$301FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$155Average$279FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$258Average$496FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$274Average$399FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$315Average$503FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$317Average$474FlexibilityNo cancel feeOn-time63%
DeltaCheapest$324Average$492FlexibilityNo cancel feeOn-timeN/A
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.