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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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$209
(Cheapflightsfares)

One-way from

$108
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$317

Good round-trip deal

$346 or less

Good one-way deal

$187 or less
From Chicago (CHI) to Puerto Rico
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One-way flight from Chicago (CHI) to Puerto Rico
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Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Puerto Rico.
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Price to beat on a one-way flight from Chicago (CHI) to Puerto Rico.
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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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Sat 10/255:18 pmSJU - ORD
1 stop19h 15mSpirit Airlines
Deal found 9/11$208
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 9/236:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Tue 9/306:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/11$209
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Thu 9/256:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Thu 10/27:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 9/10$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Fri 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$212
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$213
This Frontier deal was found by Cheapflights users on 9/9. 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.
Sat 10/256:40 amORD - SJU
1 stop7h 44mFrontier
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Deal found 9/9$214
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Fri 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Tue 10/73:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$215
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Sat 12/610:15 amORD - SJU
1 stop8h 29mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/10$216
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/117:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Sat 10/189:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 9/11$217
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Tue 10/143:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$218
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/69:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Tue 10/216:22 amSJU - ORD
1 stop31h 23mMultiple Airlines
Deal found 9/10$219
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Wed 10/16:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Mon 10/67:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/10$220

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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.

Fly from

Chicago

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 10/24

11:51 am-2:04 am

2 stops13h 13m

Aguadilla Borinquen

Wed 10/29

3:29 am-12:26 pm

1 stop9h 57m

$263

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 9/18

8:49 pm-2:27 am

1 stop28h 38m

Aguadilla Borinquen

Sun 9/21

3:32 am-7:44 pm

1 stop17h 12m

$268

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

Aguadilla Borinquen

Tue 10/14

2:59 am-3:08 pm

1 stop13h 09m

$276

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/22

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$280

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 10/9

9:24 am-2:04 am

1 stop15h 40m

Aguadilla Borinquen

Mon 10/13

2:59 am-9:33 pm

1 stop19h 34m

$281

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

Aguadilla Borinquen

Sat 10/11

11:03 am-6:33 pm

1 stop8h 30m

$286

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 9/25

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Sun 9/28

10:15 am-7:44 pm

1 stop10h 29m

$288

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 9/25

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Mon 9/29

10:15 am-7:44 pm

1 stop10h 29m

$288

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/3

1:36 pm-12:47 am

1 stop10h 11m

San Juan Luis Munoz Marin Intl

Mon 10/6

3:03 am-12:10 pm

1 stop10h 07m

$304

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 10/19

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

Sat 10/25

3:56 pm-8:03 pm

Nonstop5h 07m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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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, 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 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 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 September 11, 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 September 11, 2025.

The most flights from CHI to PR0 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 11, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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, JetBlue, and United Airlines can get you from Chicago to Puerto Rico in just under 4h 52m. Your travel time can differ by up to 8h 21m. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $126. Frontier flights start at $130 while deals on United Airlines start at $153 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: Spirit Airlines (79%), American Airlines (77%), Alaska Airlines( 77%).

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

    On average you can expect to pay $463 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $127 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $177.

  • 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 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

Browse thousands of different options on Cheapflights for your next trip

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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 Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
St. Louis to Punta Cana flights
O'Hare Intl to Castries flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Christiansted flights
St. Louis to Oranjestad flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
Midway to George Town flights
St. Louis to Georgetown flights
St. Louis to Simpson Bay flights
O'Hare Intl to Road Town flights
St. Louis to Nassau flights
O'Hare Intl to Kingston flights
St. Louis to Willemstad flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Freeport flights
St. Louis to George Town flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Castries flights
Midway to Castries flights
O'Hare Intl to Basseterre flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Santiago de los Caballeros 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$305FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$335FlexibilityNo cancel feeOn-time65%
DeltaCheapest$212Average$406FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$422FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$274Average$496FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$347Average$518FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$360Average$487FlexibilityNo cancel feeOn-time63%

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