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$115+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
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 July 28, 2025.

Round-trip from

$227
(CheapOair)

One-way from

$115
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$280 or less

Good one-way deal

$150 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. 12% potential increase in price ($54 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 July 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 July 28, 2025.

This CheapOair deal was found by Cheapflights users on 7/28. 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 10/48:56 pmORD - SJU
1 stop17h 05mMultiple Airlines
Sat 10/113:21 pmSJU - ORD
1 stop9h 00mMultiple Airlines
Deal found 7/28$227
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Wed 9/105:17 pmORD - SJU
1 stop6h 27mSpirit Airlines
Thu 9/2511:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Deal found 7/28$228
This eDestinos deal was found by Cheapflights users on 7/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:46 pmORD - SJU
1 stop22h 22mFrontier
Sat 9/64:42 pmSJU - ORD
1 stop28h 02mFrontier
Deal found 7/26$234
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 9/136:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/27$236
This Priceline deal was found by Cheapflights users on 7/26. 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 8/169:08 amORD - BQN
1 stop15h 53mFrontier
Sat 8/233:39 amBQN - ORD
1 stop16h 02mFrontier
Deal found 7/26$254
This Trip.com deal was found by Cheapflights users on 7/26. 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.
Sat 8/307:46 pmORD - PSE
1 stop14h 12mFrontier
Fri 9/510:15 amPSE - ORD
1 stop10h 29mFrontier
Deal found 7/26$261
This Trip.com deal was found by Cheapflights users on 7/26. 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.
Sat 8/235:16 pmORD - BQN
1 stop8h 28mMultiple Airlines
Fri 8/293:39 amBQN - ORD
1 stop19h 43mMultiple Airlines
Deal found 7/26$312
This Priceline deal was found by Cheapflights users on 7/28. 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 9/278:34 amORD - BQN
1 stop16h 59mJetBlue
Tue 10/75:01 amBQN - ORD
1 stop8h 09mJetBlue
Deal found 7/28$386
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Mon 9/81:12 pmORD - BQN
1 stop8h 57mUnited Airlines
Sun 9/1412:15 amBQN - ORD
1 stop8h 23mUnited Airlines
Deal found 7/26$391
This Trip.com deal was found by Cheapflights users on 7/26. 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.
Sat 8/3011:36 amORD - PSE
2 stops22h 22mMultiple Airlines
Fri 9/510:15 amPSE - ORD
1 stop12h 43mMultiple Airlines
Deal found 7/26$586
This Expedia deal was found by Cheapflights users on 7/26. 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.
Sat 8/309:40 amORD - PSE
2 stops14h 03mJetBlue
Fri 9/55:20 amPSE - ORD
2 stops13h 34mJetBlue
Deal found 7/26$599
This United deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/102:20 pmORD - MAZ
1 stop21h 07mMultiple Airlines
Wed 1/74:13 pmMAZ - ORD
2 stops8h 59mMultiple Airlines
Deal found 7/26$751

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 July 28, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 10/4

8:56 pm-3:01 pm

1 stop17h 05m

San Juan Luis Munoz Marin Intl

Sat 10/11

3:21 pm-11:21 pm

1 stop9h 00m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/10

5:17 pm-12:44 am

1 stop6h 27m

San Juan Luis Munoz Marin Intl

Thu 9/25

11:59 am-10:48 pm

1 stop11h 49m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

7:46 pm-7:08 pm

1 stop22h 22m

San Juan Luis Munoz Marin Intl

Sat 9/6

4:42 pm-7:44 pm

1 stop28h 02m

$234

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/13

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$236

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 8/16

9:08 am-2:01 am

1 stop15h 53m

Aguadilla Borinquen

Sat 8/23

3:39 am-6:41 pm

1 stop16h 02m

$254

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 8/30

7:46 pm-10:58 am

1 stop14h 12m

Ponce Mercedita

Fri 9/5

10:15 am-7:44 pm

1 stop10h 29m

$261

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 8/23

5:16 pm-2:44 am

1 stop8h 28m

Aguadilla Borinquen

Fri 8/29

3:39 am-10:22 pm

1 stop19h 43m

$312

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 9/27

8:34 am-2:33 am

1 stop16h 59m

Aguadilla Borinquen

Tue 10/7

5:01 am-12:10 pm

1 stop8h 09m

$386

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Mon 9/8

1:12 pm-11:09 pm

1 stop8h 57m

Aguadilla Borinquen

Sun 9/14

12:15 am-7:38 am

1 stop8h 23m

$391

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 8/30

11:36 am-10:58 am

2 stops22h 22m

Ponce Mercedita

Fri 9/5

10:15 am-9:58 pm

1 stop12h 43m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 25 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 July 28, 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 July 28, 2025.

The most flights from CHI to PR0 are scheduled on a Saturday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 28, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and JetBlue 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
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,034 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $115. Frontier flights start at $118 while deals on Southwest start at $182 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 - Ponce Mercedita.

  • 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: Air Canada (83%), United Airlines (83%), Air New Zealand( 83%).

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

    On average you can expect to pay $575 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $117 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $215.

  • 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

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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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
O'Hare Intl to Nassau flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to George Town flights
St. Louis to Punta Cana flights
Midway to Oranjestad flights
St. Louis to Nassau flights
O'Hare Intl to Simpson Bay flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
Midway to Nassau flights
St. Louis to Montego Bay flights
Midway to Santo Domingo flights
O'Hare Intl to Ponce flights
St. Louis to Oranjestad flights
O'Hare Intl to Christiansted flights
Midway to George Town flights
Midway to Providenciales flights
O'Hare Intl to Port of Spain flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kingston flights
O'Hare Intl to Road Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
St. Louis to Willemstad flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to St. John's flights
Moline to Luis Munoz Marin Intl flights
Midway to Castries flights
St. Louis to Santo Domingo flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to George Town flights
St. Louis to Georgetown flights
O'Hare Intl to Havana flights
O'Hare Intl to Basseterre 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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$296FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$333FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$406FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$495FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$418FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$346Average$516FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$352Average$485FlexibilityNo cancel feeOn-time63%

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