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$85+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Round-trip from

$210
(Kiwi.com)

One-way from

$85
(Priceline)

Popular in

December

Cheapest in

April

Average price

$381

Good round-trip deal

$358 or less

Good one-way deal

$181 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. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/2010:12 amORD - SJU
1 stop8h 15mSpirit Airlines
Tue 11/254:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 11/1$210
This Priceline deal was found by Cheapflights users on 11/2. 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.
Wed 12/1012:09 pmORD - SJU
1 stop10h 07mMultiple Airlines
Sun 12/141:59 amSJU - ORD
1 stop14h 04mMultiple Airlines
Deal found 11/2$211
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:52 pmORD - SJU
2 stops32h 57mMultiple Airlines
Mon 2/94:11 pmSJU - ORD
1 stop9h 24mMultiple Airlines
Deal found 11/3$212
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/14:58 pmORD - SJU
1 stop15h 51mMultiple Airlines
Fri 12/53:06 pmSJU - ORD
1 stop7h 36mMultiple Airlines
Deal found 11/2$213
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/205:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Thu 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 11/2$216
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Tue 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Mon 12/88:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/2$218
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Deal found 11/2$219
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Tue 12/95:00 pmSJU - MDW
2 stops17h 46mMultiple Airlines
Deal found 11/2$220
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/1212:15 pmORD - SJU
1 stop9h 41mMultiple Airlines
Sat 1/314:11 pmSJU - ORD
2 stops18h 59mMultiple Airlines
Deal found 11/2$221
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sun 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Sat 11/224:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 11/2$222
This Priceline deal was found by Cheapflights users on 11/3. 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.
Mon 11/178:00 amORD - SJU
Nonstop4h 36mMultiple Airlines
Wed 11/193:59 amSJU - ORD
1 stop15h 14mMultiple Airlines
Deal found 11/3$223
This Trip.com deal was found by Cheapflights users on 11/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:30 pmMDW - SJU
1 stop7h 24mFrontier
Sun 11/232:25 amSJU - MDW
1 stop17h 41mFrontier
Deal found 11/3$223

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 November 3, 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

Sun 1/25

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

11:18 am-11:44 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-1:55 pm

2 stops9h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-2:30 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-12:01 pm

1 stop7h 46m

$227

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 11/16

5:25 am-3:04 am

1 stop19h 39m

Aguadilla Borinquen

Wed 11/19

3:55 am-5:13 pm

1 stop15h 18m

$232

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$267

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:35 pm-10:05 pm

2 stops9h 30m

$277

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/2

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-1:40 pm

2 stops9h 40m

$292

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:35 am-11:57 am

Nonstop5h 22m

$302

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 12/25

6:45 am-4:26 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Tue 1/6

11:15 am-7:45 pm

1 stop10h 30m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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, February is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $127). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $188). 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 November 3, 2025.

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 46% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings 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 November 3, 2025.

The most flights from CHI to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 November 3, 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
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
3,117 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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?

    United Airlines, Delta, and Southwest can get you from Chicago to Puerto Rico in just under 4h 40m. Your travel time can differ by up to 5h 46m. 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 Frontier, which is currently one of the cheapest options available, starting at $85. United Airlines flights start at $114 while deals on Delta start at $114 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: American Airlines (94%), Alaska Airlines (89%), Spirit Airlines( 72%).

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

    On average you can expect to pay $680 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $113 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $176.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $127). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $188). 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
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Nassau flights
O'Hare Intl to George Town flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Montego Bay flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
St. Louis to Punta Cana flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Bridgetown flights
St. Louis to Oranjestad flights
Midway to George Town flights
Midway to Nassau flights
Midway to Providenciales flights
St. Louis to Montego Bay flights
Midway to Simpson Bay flights
O'Hare Intl to Christiansted flights
O'Hare Intl to St. George's flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
St. Louis to Georgetown flights
St. Louis to Simpson Bay flights
O'Hare Intl to Road Town flights
Midway to Santo Domingo flights
St. Louis to Santo Domingo flights
St. Louis to Castries flights
O'Hare Intl to Port of Spain flights
St. Louis to Nassau flights
St. Louis to Bridgetown flights
O'Hare Intl to Ponce flights
Moline to Luis Munoz Marin Intl flights
St. Louis to Willemstad flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Kralendijk flights
Peoria to Luis Munoz Marin Intl 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$311FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$318FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$400FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$276Average$496FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$358Average$526FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$380Average$490FlexibilityNo cancel feeOn-time63%

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