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Puerto Rico

$57+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
1 adult, Economy
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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 October 31, 2024.

This Frontier deal was found by Cheapflights users on 10/29. 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 12/812:36 pmMDW - SJU
1 stop11h 56mFrontier
Fri 12/135:03 pmSJU - MDW
1 stop9h 17mFrontier
Deal found 10/29$168
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Fri 12/66:07 pmORD - SJU
1 stop21h 16mMultiple Airlines
Wed 12/112:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 10/30$169
This FareScan deal was found by Cheapflights users on 10/31. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:10 pmORD - SJU
1 stop12h 51mSpirit Airlines
Tue 12/1010:34 amSJU - ORD
1 stop11h 41mSpirit Airlines
Deal found 10/31$171
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Thu 11/146:30 amORD - SJU
1 stop17h 19mFrontier
Sun 11/1710:12 pmSJU - ORD
1 stop15h 40mFrontier
Deal found 10/30$175
This eDestinos deal was found by Cheapflights users on 10/30. 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.
Tue 12/39:34 amMDW - SJU
2 stops16h 00mMultiple Airlines
Wed 12/116:20 amSJU - MDW
1 stop7h 22mMultiple Airlines
Deal found 10/30$200
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Thu 12/129:35 amORD - BQN
1 stop15h 13mFrontier
Tue 12/245:53 pmBQN - ORD
1 stop17h 31mFrontier
Deal found 10/30$239
This JetBlue deal was found by Cheapflights users on 10/30. 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.
Sun 12/88:51 amORD - SJU
1 stop7h 44mJetBlue
Tue 12/107:00 amSJU - ORD
1 stop10h 53mJetBlue
Deal found 10/30$289
This Southwest deal was found by Cheapflights users on 10/30. 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 12/910:00 amMDW - SJU
1 stop7h 00mSouthwest
Tue 12/1711:45 amSJU - MDW
2 stops9h 10mSouthwest
Deal found 10/30$384
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Wed 12/111:13 pmORD - CPX
2 stops17h 02mMultiple Airlines
Wed 12/1810:00 amCPX - ORD
1 stop12h 13mMultiple Airlines
Deal found 10/31$426
This United Airlines deal was found by Cheapflights users on 10/30. 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 11/1311:51 amORD - BQN
1 stop10h 06mUnited Airlines
Fri 11/151:09 amBQN - ORD
1 stop10h 01mUnited Airlines
Deal found 10/30$456
This Delta deal was found by Cheapflights users on 10/30. 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.
Thu 11/2810:41 amMDW - SJU
1 stop10h 41mDelta
Tue 12/31:50 pmSJU - MDW
1 stop9h 56mDelta
Deal found 10/30$467
This eDestinos deal was found by Cheapflights users on 10/29. 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.
Thu 11/73:59 pmORD - BQN
2 stops21h 17mMultiple Airlines
Mon 11/119:12 pmBQN - ORD
2 stops46h 18mMultiple Airlines
Deal found 10/29$656

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/5

5:52 pm-2:21 am

1 stop6h 29m

$83

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/10

8:02 pm-5:43 pm

1 stop19h 41m

$89

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/9

2:52 pm-1:52 am

1 stop9h 00m

$100

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

8:51 am-7:19 pm

1 stop8h 28m

$143

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/26

4:01 pm-2:38 am

1 stop8h 37m

$84

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/15

1:51 pm-12:04 am

1 stop8h 13m

$187

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/22

7:30 am-9:40 pm

2 stops12h 10m

$192

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 1/14

2:15 pm-11:57 pm

1 stop7h 42m

$192

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 11/3

5:00 am-4:18 pm

1 stop9h 18m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 11/9

4:24 pm-6:54 pm

2 stops24h 30m

$114

Flights are sorted by cheapest first

Deals found on 10/30

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.

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 October 31, 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.

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 October 31, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Frontier, Delta and Spirit Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,240 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

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
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

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.

  • Can I find flights from Chicago to Puerto Rico for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Puerto Rico for under $200. The cheapest flight booked recently is on Spirit Airlines for just $126, but on average you can expect to pay $524.

  • Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?

    Cheapflights has at least 4 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $338.

  • Are there last-minute flights available from Chicago to Puerto Rico for under $200?

    There are currently 10+ open flights from Chicago to Puerto Rico within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago to Puerto Rico?

    Nonstop flights can be found on the following days: Sunday, Thursday, Friday, Saturday.

  • How many flights depart from Chicago to Puerto Rico on average per day?

    2 flight departures from Chicago to Puerto Rico per day on average.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Chicago to Puerto Rico?

    Spirit Airlines, Frontier, and Southwest can get you from Chicago to Puerto Rico in just under 4h 33m. Your travel time can differ by up to 11h 36m. The distance from Chicago to Puerto Rico is about 2085 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 $57. Spirit Airlines flights start at $68 while deals on JetBlue start at $143 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: Spirit Airlines (83%), Air Canada (45%), United Airlines( 45%).

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

    On average you can expect to pay $735 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $83 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $135.

  • What does ORD to SJU mean?

    Chicago O'Hare Intl Airport is ORD and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Aguadilla Borinquen Airport (BQN), Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS).

  • Can I find deals for flights from Chicago to Puerto Rico that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Puerto Rico flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Puerto Rico with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Puerto Rico flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Puerto Rico that allow pets onboard?

    Many airlines flying from Chicago to Puerto Rico offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Puerto Rico?

    Yes, you can often find last-minute deals on Chicago to Puerto Rico flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Puerto Rico flight deals updated?

    The Chicago to Puerto Rico flight deals you see on this page were last updated on 10/31.

  • 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 Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Punta Cana flights
O'Hare Intl to George Town flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Castries flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
Midway to Oranjestad flights
O'Hare Intl to Bridgetown flights
St. Louis to Punta Cana flights
O'Hare Intl to Willemstad flights
Midway to Providenciales flights
O'Hare Intl to Kingston flights
O'Hare Intl to Christiansted flights
Midway to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
St. Louis to Montego Bay flights
O'Hare Intl to Puerto Plata flights
St. Louis to Saint Thomas Island flights
Midway to Simpson Bay flights
O'Hare Intl to Basseterre flights
St. Louis to Willemstad flights
St. Louis to George Town flights
St. Louis to Providenciales flights
St. Louis to Oranjestad flights
Midway to Kingston flights
O'Hare Intl to Port of Spain flights
Moline to Montego Bay flights
O'Hare Intl to Gregory Town flights
St. Louis to Nassau flights
St. Louis to Castries flights
Midway to Castries flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
St. Louis to Christiansted flights
O'Hare Intl to Aguadilla flights
Moline to Luis Munoz Marin Intl flights
St. Louis to Simpson Bay flights
O'Hare Intl to Georgetown 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$296FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$274FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$408FlexibilityNo cancel feeOn-time62%
DeltaCheapest$204Average$580FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$501FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$267Average$409FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$325Average$499FlexibilityNo cancel feeOn-time71%
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