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$63+ 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
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
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 noviembre 20, 2024.

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 noviembre 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
sáb. 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
mié. 12/112:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/20$170
This Trip.com deal was found by Cheapflights users on 11/20. 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.
lun. 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
jue. 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This FlightHub deal was found by Cheapflights users on 11/18. 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.
vie. 12/66:07 pmORD - SJU
1 stop21h 16mFrontier
mar. 12/246:00 amSJU - ORD
1 stop29h 24mFrontier
Deal found 11/18$175
This FlightHub deal was found by Cheapflights users on 11/19. 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.
dom. 12/85:25 amORD - SJU
2 stops12h 57mMultiple Airlines
jue. 12/127:16 pmSJU - ORD
1 stop16h 38mMultiple Airlines
Deal found 11/19$176
This United Airlines deal was found by Cheapflights users on 11/19. 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.
lun. 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
lun. 12/162:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Deal found 11/19$216
This eDestinos deal was found by Cheapflights users on 11/19. 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.
dom. 12/1512:36 pmMDW - SJU
2 stops35h 21mMultiple Airlines
mié. 1/224:53 pmSJU - MDW
2 stops27h 33mMultiple Airlines
Deal found 11/19$240
This Southwest deal was found by Cheapflights users on 11/19. 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.
jue. 12/121:30 pmMDW - SJU
1 stop9h 15mSouthwest
sáb. 12/147:20 amSJU - MDW
2 stops8h 50mSouthwest
Deal found 11/19$297
This Delta deal was found by Cheapflights users on 11/20. 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.
mar. 12/106:00 amMDW - SJU
1 stop9h 15mDelta
lun. 12/163:25 pmSJU - MDW
1 stop8h 41mDelta
Deal found 11/20$379
This FlightHub deal was found by Cheapflights users on 11/20. 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.
dom. 12/227:29 pmORD - PSE
1 stop18h 49mFrontier
lun. 12/305:08 pmPSE - ORD
1 stop19h 20mFrontier
Deal found 11/20$395
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/197:29 pmORD - BQN
1 stop29h 14mFrontier
jue. 12/265:42 pmBQN - ORD
1 stop18h 12mFrontier
Deal found 11/19$433
This Mytrip deal was found by Cheapflights users on 11/20. 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.
jue. 12/193:31 pmORD - MAZ
2 stops15h 13mMultiple Airlines
jue. 12/267:05 amMAZ - ORD
2 stops19h 28mMultiple Airlines
Deal found 11/20$465
This United Airlines deal was found by Cheapflights users on 11/19. 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.
sáb. 12/72:50 pmORD - BQN
1 stop7h 07mUnited Airlines
sáb. 12/141:09 amBQN - ORD
1 stop8h 35mUnited Airlines
Deal found 11/19$484

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

lun. 2/3

5:28 pm-2:48 am

1 stop7h 20m

Aguadilla Borinquen

sáb. 2/8

3:51 am-9:52 am

1 stop8h 01m

$146

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

mié. 12/18

4:43 pm-8:13 pm

Nonstop5h 30m

$170

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

vie. 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 12/6

6:07 pm-5:23 pm

1 stop21h 16m

San Juan Luis Munoz Marin Intl

mar. 12/24

6:00 am-9:24 am

1 stop29h 24m

$175

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 12/8

5:25 am-8:22 pm

2 stops12h 57m

San Juan Luis Munoz Marin Intl

jue. 12/12

7:16 pm-9:54 am

1 stop16h 38m

$176

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

dom. 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

mié. 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

lun. 12/16

2:05 am-8:59 am

1 stop8h 54m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

sáb. 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 1/28

6:00 am-2:20 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

vie. 2/7

2:02 pm-10:20 pm

1 stop10h 18m

$334

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

lun. 2/3

2:15 pm-11:57 pm

1 stop7h 42m

Aguadilla Borinquen

vie. 2/7

1:09 am-7:44 am

1 stop8h 35m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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.

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 $335). 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 noviembre 20, 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 noviembre 20, 2024.

The most flights from CHI to PR0 are scheduled on a Wednesday (7 on average). You will have fewer flight options on Monday, 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 noviembre 20, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, United Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $63. Spirit Airlines flights start at $91 while deals on United Airlines start at $105 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: Air Canada (90%), United Airlines (90%), Air New Zealand( 90%).

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

    On average you can expect to pay $741 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $90 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $117.

  • 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 $335). 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 Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
O'Hare Intl to Castries flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Oranjestad flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Willemstad flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Puerto Plata flights
St. Louis to Saint Thomas Island flights
Midway to Providenciales flights
Midway to Simpson Bay flights
St. Louis to Montego Bay flights
O'Hare Intl to Kralendijk flights
Midway to George Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
O'Hare Intl to Basseterre flights
St. Louis to Christiansted flights
Midway to Santo Domingo flights
St. Louis to Oranjestad flights
St. Louis to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
Moline to Montego Bay flights
O'Hare Intl to Gregory Town flights
St. Louis to Providenciales flights
St. Louis to Willemstad flights
St. Louis to Nassau flights
O'Hare Intl to St. George's flights
St. Louis to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
Peoria to Punta Cana flights
O'Hare Intl to Freeport flights
O'Hare Intl to Road Town 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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$291FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$162Average$278FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$264Average$494FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$452FlexibilityNo cancel feeOn-time63%
DeltaCheapest$324Average$548FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$499FlexibilityNo cancel feeOn-time71%
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