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Puerto Rico

$63+ Cheap flights from Illinois 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.
ORD — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Illinois to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) 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 November 21, 2024.

Find flight deals from Illinois to Puerto Rico

Cheapest flights from Illinois to Puerto Rico
Explore the most affordable flight options available from Illinois to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 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.
Sat 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Thu 12/122:17 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.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Sun 12/89:35 amORD - SJU
1 stop26h 19mFrontier
Thu 12/125:05 pmSJU - ORD
1 stop18h 49mFrontier
Deal found 11/21$175
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/89:35 amORD - SJU
1 stop26h 19mMultiple Airlines
Thu 12/122:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 11/20$177
This Priceline deal was found by Cheapflights users on 11/21. 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.
Thu 12/129:35 amORD - BQN
1 stop15h 13mFrontier
Wed 12/183:58 amBQN - ORD
1 stop8h 06mFrontier
Deal found 11/21$178
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Sat 12/143:20 amSJU - MDW
2 stops45h 25mMultiple Airlines
Deal found 11/20$254
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/45:02 pmSTL - SJU
1 stop20h 58mFrontier
Sun 2/93:53 pmSJU - STL
1 stop9h 38mFrontier
Deal found 11/20$268
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/63:34 pmSTL - SJU
2 stops28h 56mMultiple Airlines
Sun 12/159:32 pmSJU - STL
2 stops28h 01mMultiple Airlines
Deal found 11/20$275
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.
Wed 12/256:00 amSTL - SJU
1 stop9h 15mDelta
Mon 12/306:30 amSJU - STL
1 stop11h 42mDelta
Deal found 11/20$303
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Sun 12/81:10 pmSPI - SJU
2 stops20h 40mAmerican Airlines
Thu 12/125:30 amSJU - SPI
2 stops9h 09mAmerican Airlines
Deal found 11/21$311
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/712:25 pmMDW - SJU
2 stops10h 05mSouthwest
Tue 12/106:10 amSJU - MDW
2 stops10h 00mSouthwest
Deal found 11/20$312
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Mon 12/162:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Deal found 11/21$316

Find flights from Illinois to Puerto Rico within your budget

Customize your flight search to find flights from Illinois 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 November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Thu 12/12

2:17 pm-5:47 pm

Nonstop5h 30m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

8:14 pm-11:18 am

1 stop13h 04m

San Juan Luis Munoz Marin Intl

Wed 1/15

4:49 pm-1:50 pm

1 stop23h 01m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Fri 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/8

9:35 am-1:54 pm

1 stop26h 19m

San Juan Luis Munoz Marin Intl

Thu 12/12

5:05 pm-9:54 am

1 stop18h 49m

$175

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 12/12

9:35 am-2:48 am

1 stop15h 13m

Aguadilla Borinquen

Wed 12/18

3:58 am-10:04 am

1 stop8h 06m

$178

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

Sat 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 2/10

5:05 pm-11:30 am

1 stop16h 25m

San Juan Luis Munoz Marin Intl

Sat 2/22

6:05 pm-7:07 am

2 stops15h 02m

$263

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 1/21

11:09 am-11:45 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Fri 1/31

3:23 pm-8:56 pm

1 stop7h 33m

$264

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 1/20

5:05 pm-2:19 am

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 1/28

12:12 pm-11:31 pm

1 stop13h 19m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 55 results
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Best time to book a flight from Illinois to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Illinois 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 Illinois to Puerto Rico

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

What is the cheapest month to book a flight from Illinois to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $254). Flying from Illinois 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 IL to PR?

Find hourly flight availability from Illinois 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 November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Puerto Rico as you normally would.

Weekly flight availability from Illinois to Puerto Rico

Explore weekly flight availability from Illinois 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 November 21, 2024.

The most flights from USIL 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 November 21, 2024.
Read through reviews of airlines operating flights from Illinois to Puerto Rico, such as Spirit Airlines, Frontier and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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

JetBlue
7.5
Good
3,396 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

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 Illinois 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 Illinois to Puerto Rico one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $63. Users have also found prices from $91 and $105 on Spirit Airlines and United Airlines, respectively.

  • Can I find deals for flights from Illinois to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Illinois to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Puerto Rico.

  • Can I find deals for business class flights from Illinois to Puerto Rico?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $254). Flying from Illinois 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 Illinois to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Illinois to Puerto Rico

Discover the top 7 airlines that operate flights from Illinois 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 November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$291FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$162Average$278FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$644FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$264Average$494FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$452FlexibilityNo cancel feeOn-time63%
DeltaCheapest$319Average$536FlexibilityNo cancel feeOn-timeN/A
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