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Puerto Rico

$101+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
May 3 — May 101
Sat 5/3
Sat 5/10
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 April 28, 2025.

Round-trip from

$195
(Cheapflightsfares)

One-way from

$101
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$352

Good round-trip deal

$337 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 ($67 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 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:05 amORD - SJU
1 stop13h 02mSpirit Airlines
Fri 5/308:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/28$195
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Fri 5/235:10 amORD - SJU
1 stop9h 05mMultiple Airlines
Fri 5/308:12 pmSJU - ORD
1 stop13h 38mMultiple Airlines
Deal found 4/28$229
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:30 amMDW - SJU
1 stop10h 14mFrontier
Wed 5/73:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/27$298
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Thu 5/84:15 pmORD - BQN
1 stop8h 42mFrontier
Wed 5/142:47 amBQN - ORD
1 stop21h 45mFrontier
Deal found 4/28$299
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/154:15 pmORD - SJU
1 stop6h 50mFrontier
Mon 5/1910:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 4/28$308
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Thu 5/154:15 pmORD - PSE
1 stop15h 41mFrontier
Mon 5/199:46 amPSE - ORD
1 stop14h 46mFrontier
Deal found 4/28$309
This JetBlue deal was found by Cheapflights users on 4/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/304:03 pmORD - SJU
1 stop8h 46mJetBlue
Tue 6/38:00 amSJU - ORD
1 stop11h 36mJetBlue
Deal found 4/27$324
This Trip.com deal was found by Cheapflights users on 4/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/282:53 pmMDW - SJU
1 stop7h 14mMultiple Airlines
Wed 6/42:54 pmSJU - MDW
1 stop8h 44mMultiple Airlines
Deal found 4/28$342
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1311:30 amORD - MAZ
1 stop20h 14mMultiple Airlines
Sat 5/174:13 pmMAZ - ORD
2 stops17h 37mMultiple Airlines
Deal found 4/28$379
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/611:05 amMDW - SJU
1 stop7h 20mSouthwest
Wed 10/86:10 amSJU - MDW
2 stops14h 00mSouthwest
Deal found 4/28$381
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:00 amMDW - SJU
1 stop9h 33mDelta
Wed 5/2812:50 pmSJU - MDW
1 stop9h 37mDelta
Deal found 4/28$391
This Trip.com deal was found by Cheapflights users on 4/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/197:47 amORD - BQN
1 stop17h 10mMultiple Airlines
Thu 5/222:59 amBQN - ORD
2 stops10h 47mMultiple Airlines
Deal found 4/28$417

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 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 5/24

5:05 am-7:07 pm

1 stop13h 02m

San Juan Luis Munoz Marin Intl

Fri 5/30

8:12 pm-8:50 am

1 stop13h 38m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/23

5:10 am-3:15 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Fri 5/30

8:12 pm-8:50 am

1 stop13h 38m

$229

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 5/4

8:30 am-7:44 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Thu 5/8

10:46 am-11:39 pm

1 stop13h 53m

$298

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Mon 5/12

6:00 am-6:29 pm

1 stop13h 29m

$299

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 5/8

4:15 pm-1:57 am

1 stop8h 42m

Aguadilla Borinquen

Wed 5/14

2:47 am-11:32 pm

1 stop21h 45m

$299

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 5/15

4:15 pm-8:56 am

1 stop15h 41m

Ponce Mercedita

Mon 5/19

9:46 am-11:32 pm

1 stop14h 46m

$309

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/30

4:03 pm-1:49 am

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Tue 6/3

8:00 am-6:36 pm

1 stop11h 36m

$324

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/28

2:53 pm-11:07 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Wed 6/4

2:54 pm-10:38 pm

1 stop8h 44m

$342

ChicagoMayagüez

ORD - MAZ

ORDMAZ

Chicago O'Hare Intl

Tue 5/13

11:30 am-8:44 am

1 stop20h 14m

Mayagüez Eugenio M De Hostos

Sat 5/17

4:13 pm-8:50 am

2 stops17h 37m

$379

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/12

2:40 pm-11:55 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Thu 5/29

3:25 pm-10:40 pm

1 stop8h 15m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 31 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 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 April 28, 2025.

The most flights from CHI to PR0 are scheduled on a Saturday (10 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 28, 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
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $101. Frontier flights start at $145 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%), American Airlines (83%), Air Canada( 82%).

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

    On average you can expect to pay $757 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $133 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $188.

  • 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
Midway to Punta Cana flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
St. Louis to Punta Cana flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santo Domingo flights
Midway to Oranjestad flights
O'Hare Intl to Providenciales flights
St. Louis to Montego Bay flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
Midway to Saint Thomas Island flights
St. Louis to Nassau flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Kingston flights
Midway to Nassau flights
Midway to Providenciales flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Oranjestad flights
Midway to Santo Domingo flights
O'Hare Intl to Road Town flights
O'Hare Intl to St. John's flights
St. Louis to Providenciales flights
St. Louis to Castries flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Port of Spain flights
Midway to George Town flights
O'Hare Intl to Ponce flights
Midway to Simpson Bay flights
St. Louis to Simpson Bay flights
O'Hare Intl to Havana flights
O'Hare Intl to Castries flights
St. Louis to Willemstad flights
O'Hare Intl to St. George's flights
O'Hare Intl to The Valley flights
O'Hare Intl to Freeport flights
Midway to Kingston flights
Moline to Saint Thomas Island flights
Peoria to Luis Munoz Marin Intl 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$307FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$279FlexibilityNo cancel feeOn-time65%
DeltaCheapest$216Average$459FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$491FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$404FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$335Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$345Average$480FlexibilityNo cancel feeOn-time63%

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