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Puerto Rico

$108+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
1 adult, Economy
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Cheap 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 May 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 7/2912:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/37:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$219
This Frontier deal was found by Cheapflights users on 5/5. 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 7/1712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Tue 8/47:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$221
This American Airlines deal was found by Cheapflights users on 5/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Tue 8/187:14 pm
SJU
-
ORD
1 stop13h 20m
American Airlines
Deal found 5/6$222
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sun 7/1212:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/37:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$223
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sat 7/188:05 am
ORD
-
SJU
1 stop7h 00m
Frontier
Mon 8/37:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$224
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 8/191:48 pm
ORD
-
SJU
1 stop7h 41m
Delta
Wed 9/22:40 pm
SJU
-
ORD
1 stop10h 17m
Delta
Deal found 5/7$226
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 8/1910:54 am
MDW
-
SJU
1 stop10h 35m
Delta
Wed 9/22:40 pm
SJU
-
MDW
1 stop8h 06m
Delta
Deal found 5/7$226
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Wed 9/26:51 am
SJU
-
ORD
1 stop8h 24m
American Airlines
Deal found 5/5$227
This Priceline deal was found by Cheapflights users on 5/3. 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.
Sat 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/229:24 am
SJU
-
ORD
1 stop14h 50m
Frontier
Deal found 5/3$228
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Mon 8/2412:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 9/76:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/5$229
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/1712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/5$230
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Sat 8/2910:33 am
SJU
-
ORD
1 stop13h 27m
American Airlines
Deal found 5/5$232

Find flight deals from Chicago to Puerto Rico

Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated May 8, 2026.

Round-trip from

$219
(Kiwi.com)

One-way from

$108
(eDestinos)

Popular in

December

Cheapest in

January

Average price

$360

Good round-trip deal

$298 or less

Good one-way deal

$133 or less
From Chicago (CHI) to Puerto Rico
Search Deals
One-way flight from Chicago (CHI) to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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

Cheapflights Fare Finder

 
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 May 8, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Tue 7/28

5:13 pm-10:57 am

1 stop16h 44m

Ponce Mercedita

Mon 8/3

10:31 am-11:05 pm

1 stop13h 34m

$321

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Mon 7/13

10:16 am-9:46 am

1 stop22h 30m

Ponce Mercedita

Mon 7/20

10:31 am-11:05 pm

1 stop13h 34m

$321

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 6/19

4:59 pm-9:42 am

1 stop15h 43m

Ponce Mercedita

Fri 6/26

10:27 am-11:19 pm

1 stop13h 52m

$321

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 5/23

5:11 pm-2:02 am

1 stop7h 51m

Aguadilla Borinquen

Thu 5/28

2:59 am-11:13 pm

1 stop21h 14m

$330

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 5/24

5:11 pm-2:02 am

1 stop7h 51m

Aguadilla Borinquen

Thu 5/28

2:59 am-11:13 pm

1 stop21h 14m

$331

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 6/19

4:59 pm-9:42 am

1 stop15h 43m

Ponce Mercedita

Sun 6/28

10:27 am-9:21 am

1 stop23h 54m

$353

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 7/10

10:16 am-9:46 am

1 stop22h 30m

Ponce Mercedita

Tue 7/14

10:31 am-11:05 pm

1 stop13h 34m

$366

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 7/25

5:13 pm-9:46 am

1 stop15h 33m

Ponce Mercedita

Sun 8/2

10:31 am-11:05 pm

1 stop13h 34m

$386

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 5/23

5:11 pm-9:07 am

1 stop14h 56m

Ponce Mercedita

Tue 5/26

10:02 am-11:13 pm

1 stop14h 11m

$456

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 6/16

8:10 pm-9:00 am

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Thu 6/25

10:20 pm-9:15 am

1 stop11h 55m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Puerto Rico

How far ahead should I book a flight from Chicago to Puerto Rico?

The best time to book flights from Chicago to Puerto Rico is 56 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $318). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $634). 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 May 8, 2026.

When flying from Chicago to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 25% versus a flight in the morning.

What is the cheapest day to fly from Chicago to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Puerto Rico. Price data was last updated on May 2, 2026.

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

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 May 8, 2026.

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

How often are flights from Chicago to Puerto Rico delayed?

About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 140 minutes.

What is the most punctual flight time for Chicago to Puerto Rico 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 Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.

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 May 8, 2026.
Peruse reviews from past customers who have flown with United Airlines,JetBlue, andAmerican Airlines from Chicago to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,693 reviews
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
JetBlue
7.2
Good
2,979 reviews
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,669 reviews
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Spirit Airlines
6.3
Okay
8,638 reviews
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Frontier
5.6
Fair
2,961 reviews
United Airlines
7.4
Good
9,693 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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.

  • How long is the flight from Chicago to Puerto Rico?

    Frontier, Southwest, and United Airlines can get you from Chicago to Puerto Rico in just under 7h 45m. Your travel time can differ by up to 8h 59m. The distance from Chicago to Puerto Rico is about 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Puerto Rico one-way?

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $75. Spirit Airlines flights start at $90 while deals on Frontier start at $95 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: Qatar Airways (95%), American Airlines (81%), Alaska Airlines( 79%).

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

    On average you can expect to pay $650 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $98 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $157.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $318). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $634). 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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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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$235FlexibilityNo cancel feeOn-time62%
FrontierCheapest$121Average$309FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$387FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$138Average$313FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$518FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$311Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$352Average$489FlexibilityNo cancel feeOn-time63%

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