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$64+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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Cheap flight deals from Chicago to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Puerto Rico (PR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2024.

Round-trip from

$148
(Frontier)

One-way from

$64
(Cheapflightsfares)
From Chicago (CHI) to Puerto Rico
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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 December 23, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/23. 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 12/301:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 1/186:14 amSJU - ORD
1 stop11h 56mSpirit Airlines
Deal found 12/23$289
This eDestinos deal was found by Cheapflights users on 12/23. 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.
Mon 12/301:00 pmORD - SJU
Nonstop4h 36mMultiple Airlines
Tue 1/148:45 amSJU - ORD
2 stops29h 02mMultiple Airlines
Deal found 12/23$322
This FlightHub deal was found by Cheapflights users on 12/23. 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.
Tue 12/316:49 pmMDW - SJU
1 stop12h 36mFrontier
Fri 1/106:00 amSJU - MDW
1 stop13h 50mFrontier
Deal found 12/23$366
This Frontier deal was found by Cheapflights users on 12/23. 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.
Tue 12/311:47 pmORD - SJU
1 stop8h 54mFrontier
Sun 1/1211:42 amSJU - ORD
1 stop13h 52mFrontier
Deal found 12/23$384
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/3011:33 amORD - SJU
1 stop10h 22mAmerican Airlines
Tue 12/319:00 amSJU - ORD
1 stop8h 51mAmerican Airlines
Deal found 12/23$418
This Gotogate deal was found by Cheapflights users on 12/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2810:49 amORD - BQN
1 stop14h 09mFrontier
Thu 1/303:51 amBQN - ORD
1 stop8h 01mFrontier
Deal found 12/22$481
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Tue 12/312:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Wed 1/82:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Deal found 12/22$494
This Trip.com deal was found by Cheapflights users on 12/23. 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.
Tue 12/316:49 pmMDW - SJU
1 stop12h 36mMultiple Airlines
Sun 1/53:28 amSJU - MDW
1 stop19h 36mMultiple Airlines
Deal found 12/23$568
This Southwest deal was found by Cheapflights users on 12/23. 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.
Thu 12/267:40 pmMDW - SJU
1 stop12h 45mSouthwest
Thu 1/3012:15 pmSJU - MDW
1 stop9h 30mSouthwest
Deal found 12/23$574
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Tue 12/242:30 pmORD - BQN
1 stop7h 27mUnited Airlines
Thu 12/261:09 amBQN - ORD
1 stop8h 35mUnited Airlines
Deal found 12/23$623
This Mytrip deal was found by Cheapflights users on 12/23. 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 12/313:31 pmORD - CPX
2 stops16h 51mMultiple Airlines
Tue 1/73:05 pmCPX - ORD
3 stops30h 14mMultiple Airlines
Deal found 12/23$699
This Priceline deal was found by Cheapflights users on 12/23. 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 12/2810:49 amORD - PSE
1 stop22h 29mFrontier
Wed 1/112:58 pmPSE - ORD
1 stop23h 06mFrontier
Deal found 12/23$906

Find flights from Chicago to Puerto Rico within your budget

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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Mon 2/10

5:28 pm-2:48 am

1 stop7h 20m

Aguadilla Borinquen

Fri 2/14

3:51 am-9:15 am

1 stop7h 24m

$148

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/20

5:28 pm-2:19 am

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Thu 1/30

9:26 pm-12:51 am

Nonstop5h 25m

$161

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/26

10:58 am-2:19 am

1 stop13h 21m

San Juan Luis Munoz Marin Intl

Mon 1/27

6:00 am-3:02 pm

1 stop11h 02m

$163

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/22

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Wed 1/29

9:26 pm-12:51 am

Nonstop5h 25m

$166

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/21

7:18 pm-9:35 am

1 stop12h 17m

San Juan Luis Munoz Marin Intl

Sat 2/22

10:35 pm-7:09 am

1 stop10h 34m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/25

7:30 am-9:21 am

2 stops23h 51m

San Juan Luis Munoz Marin Intl

Sat 2/1

8:00 am-11:29 pm

2 stops17h 29m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/22

1:15 pm-10:22 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

Tue 1/28

2:05 am-9:40 am

1 stop9h 35m

$234

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/15

1:20 pm-12:40 am

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 1/23

2:55 pm-7:45 pm

1 stop6h 50m

$279

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/1

1:22 pm-9:57 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Tue 4/8

5:05 am-12:27 pm

1 stop8h 22m

$302

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 2/1

3:56 pm-2:48 am

3 stops56h 52m

Aguadilla Borinquen

Fri 2/7

3:51 am-12:30 pm

3 stops34h 39m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 35 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.

Travel insights for flights from Chicago to Puerto Rico

Get recent, data-driven insights about flights from Chicago to Puerto Rico including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $380). 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 December 23, 2024.

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 December 23, 2024.

The most flights from CHI to PR0 are scheduled on a Saturday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 December 23, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Delta, Spirit Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,780 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,263 reviews
Southwest
8.1
Very good
4,780 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,020 reviews
Southwest
8.1
Very good
4,780 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $64. Spirit Airlines flights start at $91 while deals on Southwest start at $117 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: American Airlines (100%), Alaska Airlines (100%), Air Canada( 85%).

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

    On average you can expect to pay $687 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $64 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $135.

  • 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 March is currently the most expensive (average of $380). 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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
Midway to Montego Bay flights
O'Hare Intl to George Town 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
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
Midway to Oranjestad flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
St. Louis to Punta Cana flights
St. Louis to George Town flights
St. Louis to Saint Thomas Island flights
Midway to George Town flights
Midway to Providenciales flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to St. John's flights
St. Louis to Montego Bay flights
St. Louis to Christiansted flights
Midway to Santo Domingo flights
O'Hare Intl to Basseterre flights
St. Louis to Nassau flights
St. Louis to Oranjestad flights
St. Louis to Castries flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kingston flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to St. George's flights
St. Louis to Simpson Bay flights
O'Hare Intl to Freeport flights
O'Hare Intl to Road Town flights
St. Louis to Providenciales flights
O'Hare Intl to Castries flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Georgetown flights
Moline to Montego Bay 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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$293FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$291FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$495FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$463FlexibilityNo cancel feeOn-time63%
DeltaCheapest$307Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$498FlexibilityNo cancel feeOn-time71%
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