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Puerto Rico

$103+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 21 — Apr 281
Mon 4/21
Mon 4/28
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 April 16, 2025.

Round-trip from

$220
(Priceline)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$351

Good round-trip deal

$328 or less

Good one-way deal

$186 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. 15% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 16, 2025.

This Priceline deal was found by Cheapflights users on 4/15. 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 4/269:09 amORD - SJU
1 stop9h 31mSpirit Airlines
Thu 5/18:45 pmSJU - ORD
1 stop11h 55mSpirit Airlines
Deal found 4/15$220
This FlightHub deal was found by Cheapflights users on 4/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:47 amORD - SJU
1 stop16h 07mMultiple Airlines
Fri 5/1610:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Deal found 4/15$261
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 4/2811:00 amMDW - SJU
1 stop7h 41mFrontier
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Deal found 4/16$294
This Frontier deal was found by Cheapflights users on 4/16. 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.
Thu 4/244:30 pmORD - SJU
1 stop9h 19mFrontier
Sat 4/262:37 pmSJU - ORD
1 stop9h 59mFrontier
Deal found 4/16$298
This CheapOair deal was found by Cheapflights users on 4/16. 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 4/254:30 pmORD - PSE
1 stop15h 16mFrontier
Fri 5/29:46 amPSE - ORD
1 stop14h 46mFrontier
Deal found 4/16$308
This CheapOair deal was found by Cheapflights users on 4/15. 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 4/254:30 pmORD - BQN
1 stop8h 24mFrontier
Fri 5/22:47 amBQN - ORD
1 stop21h 45mFrontier
Deal found 4/15$308
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Wed 4/236:03 pmORD - SJU
Nonstop4h 51mUnited Airlines
Mon 5/51:05 amSJU - ORD
1 stop10h 01mUnited Airlines
Deal found 4/15$373
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:35 amMDW - SJU
1 stop9h 05mSouthwest
Tue 10/76:10 amSJU - MDW
2 stops14h 20mSouthwest
Deal found 4/15$373
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Fri 10/108:05 amORD - SJU
Nonstop4h 40mAmerican Airlines
Fri 10/243:50 pmSJU - ORD
1 stop17h 57mAmerican Airlines
Deal found 4/16$377
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Fri 9/1912:45 pmORD - BQN
1 stop9h 24mUnited Airlines
Sat 9/2012:15 amBQN - ORD
1 stop8h 16mUnited Airlines
Deal found 4/15$385
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 10/46:00 amMDW - SJU
1 stop9h 08mDelta
Sat 10/1112:57 pmSJU - MDW
1 stop9h 47mDelta
Deal found 4/16$391
This JetBlue deal was found by Cheapflights users on 4/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:03 pmORD - BQN
1 stop8h 58mJetBlue
Sun 5/255:05 amBQN - ORD
1 stop10h 59mJetBlue
Deal found 4/16$436

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 April 16, 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 4/26

9:09 am-7:40 pm

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Thu 5/1

8:45 pm-7:40 am

1 stop11h 55m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

7:47 am-12:54 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Fri 5/16

10:46 am-11:11 pm

1 stop13h 25m

$261

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/28

11:00 am-7:41 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-12:24 pm

1 stop7h 24m

$294

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/24

4:30 pm-2:49 am

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Sat 4/26

2:37 pm-11:36 pm

1 stop9h 59m

$298

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 4/25

4:30 pm-8:46 am

1 stop15h 16m

Ponce Mercedita

Fri 5/2

9:46 am-11:32 pm

1 stop14h 46m

$308

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 4/25

4:30 pm-1:54 am

1 stop8h 24m

Aguadilla Borinquen

Fri 5/2

2:47 am-11:32 pm

1 stop21h 45m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/7

6:03 pm-11:54 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:05 am-10:06 am

1 stop10h 01m

$353

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/7

8:20 am-2:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 5/14

2:50 pm-7:10 pm

Nonstop5h 20m

$372

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/3

6:35 am-4:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Tue 10/7

6:10 am-7:30 pm

2 stops14h 20m

$373

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/4

6:00 am-4:08 pm

1 stop9h 08m

San Juan Luis Munoz Marin Intl

Sat 10/11

12:57 pm-9:44 pm

1 stop9h 47m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 33 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 December is currently the most expensive (average of $336). 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 April 16, 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 April 16, 2025.

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

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 16, 2025.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Southwest, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,282 reviews
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,665 reviews
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,282 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $103. Frontier flights start at $146 while deals on JetBlue start at $162 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: United Airlines (88%), Air Canada (82%), Air New Zealand( 82%).

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

    On average you can expect to pay $839 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $101 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $213.

  • 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 December is currently the most expensive (average of $336). 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
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
O'Hare Intl to George Town flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Christiansted flights
St. Louis to Punta Cana flights
Midway to Oranjestad flights
O'Hare Intl to Providenciales flights
St. Louis to Oranjestad flights
St. Louis to Montego Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
Midway to Nassau flights
O'Hare Intl to Kingston flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Providenciales flights
St. Louis to Nassau flights
Midway to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to Road Town flights
Midway to Simpson Bay flights
O'Hare Intl to St. John's flights
O'Hare Intl to Ponce flights
St. Louis to Providenciales flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Port of Spain flights
St. Louis to Willemstad flights
St. Louis to Castries flights
St. Louis to George Town flights
St. Louis to Christiansted flights
O'Hare Intl to Freeport flights
St. Louis to Simpson Bay flights
Midway to Kingston flights
O'Hare Intl to Havana flights
St. Louis to Bridgetown flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Kralendijk 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 April 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$301FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$274FlexibilityNo cancel feeOn-time65%
DeltaCheapest$222Average$433FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$491FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$408FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$331Average$513FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$342Average$474FlexibilityNo cancel feeOn-time63%

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