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Puerto Rico

$98+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
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 March 23, 2026.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
BQN
1 stop7h 32m
Frontier
Sun 5/172:59 am
BQN
-
ORD
1 stop21h 14m
Frontier
Deal found 3/20$196
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.
Mon 4/137:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Thu 4/164:34 pm
SJU
-
ORD
Nonstop5h 15m
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.
Mon 4/137:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
-
ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18$203
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.
Wed 4/84:21 pm
ORD
-
SJU
1 stop6h 41m
Multiple Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/21$205
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:14 am
MDW
-
SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
-
MDW
1 stop8h 16m
Frontier
Deal found 3/20$205
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:34 pm
ORD
-
SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Deal found 3/19$206
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 pm
ORD
-
SJU
1 stop13h 34m
Frontier
Sat 5/166:41 pm
SJU
-
ORD
1 stop15h 56m
Frontier
Deal found 3/20$207
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.
Fri 4/106:10 pm
ORD
-
SJU
1 stop16h 39m
Multiple Airlines
Sat 4/1811:30 am
SJU
-
ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/18$208
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:52 pm
ORD
-
SJU
1 stop25h 07m
Frontier
Mon 5/46:00 am
SJU
-
ORD
1 stop18h 55m
Frontier
Deal found 3/22$209
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.
Sat 4/115:05 am
ORD
-
SJU
1 stop12h 50m
Spirit Airlines
Tue 4/147:54 pm
SJU
-
ORD
1 stop14h 42m
Spirit Airlines
Deal found 3/18$210
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
-
SJU
1 stop9h 14m
Frontier
Wed 4/1511:05 am
SJU
-
ORD
1 stop27h 48m
Frontier
Deal found 3/20$211
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
-
SJU
1 stop29h 13m
Frontier
Sat 4/183:21 am
SJU
-
MDW
1 stop29h 43m
Frontier
Deal found 3/21$211

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 March 23, 2026.

Round-trip from

$196
(Priceline)

One-way from

$98
(WAYA)

Popular in

December

Cheapest in

October

Average price

$416

Good round-trip deal

$315 or less

Good one-way deal

$175 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 March 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 March 23, 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

Wed 5/6

3:55 pm-9:07 am

1 stop16h 12m

Ponce Mercedita

Tue 5/12

10:02 am-11:13 pm

1 stop14h 11m

$264

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 5/8

5:30 pm-2:02 am

1 stop7h 32m

Aguadilla Borinquen

Sun 5/10

2:59 am-11:13 pm

1 stop21h 14m

$303

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/28

9:50 am-8:24 pm

1 stop9h 34m

San Juan Luis Munoz Marin Intl

Tue 5/5

6:15 am-4:42 pm

1 stop11h 27m

$316

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Mon 5/18

5:30 pm-9:07 am

1 stop14h 37m

Ponce Mercedita

Mon 5/25

10:02 am-11:13 pm

1 stop14h 11m

$321

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Wed 5/6

3:55 pm-9:07 am

1 stop16h 12m

Ponce Mercedita

Wed 5/13

10:02 am-11:13 pm

1 stop14h 11m

$335

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 5/22

5:30 pm-9:07 am

1 stop14h 37m

Ponce Mercedita

Wed 5/27

10:02 am-11:13 pm

1 stop14h 11m

$355

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/2

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:40 am-11:53 am

Nonstop5h 13m

$363

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 6/4

5:30 pm-9:07 am

1 stop14h 37m

Ponce Mercedita

Sun 6/7

10:02 am-11:13 pm

1 stop14h 11m

$366

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/22

2:35 pm-11:40 pm

2 stops8h 05m

San Juan Luis Munoz Marin Intl

Tue 4/28

5:35 am-1:45 pm

1 stop9h 10m

$379

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/12

5:15 am-5:05 pm

2 stops10h 50m

San Juan Luis Munoz Marin Intl

Wed 4/15

5:05 am-3:50 pm

2 stops11h 45m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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

Currently, April is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $91). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $224). 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 March 23, 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 28% 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 March 14, 2026.

Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Tuesday evenings 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 March 23, 2026.

The most flights from CHI to PR0 are scheduled on a Saturday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

How often are flights from Chicago to Puerto Rico delayed?

About 19% 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, American Airlines have had the lowest number of delays on this route, with just 17% 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 March 23, 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
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,459 reviews
United Airlines
7.4
Good
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
JetBlue
7.2
Good
2,911 reviews
United Airlines
7.4
Good
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,485 reviews
United Airlines
7.4
Good
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Spirit Airlines
6.3
Okay
8,533 reviews
United Airlines
7.4
Good
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Frontier
5.7
Fair
3,020 reviews
United Airlines
7.4
Good
9,459 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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, Delta, and United Airlines can get you from Chicago to Puerto Rico in just under 4h 56m. Your travel time can differ by up to 11h 16m. 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 $89 while deals on Frontier start at $98 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 (92%), Alaska Airlines (88%), American Airlines( 87%).

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

    On average you can expect to pay $591 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $118 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $203.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $91). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $224). 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$296FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$420FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$139Average$315FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$509FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$311Average$520FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$377Average$488FlexibilityNo cancel feeOn-time63%

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