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Puerto Rico

$103+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Illinois to Puerto Rico

Keep the following information in mind while searching for Illinois to Puerto Rico flight deals. Data was last updated July 31, 2025.

Round-trip from

$205
(Southwest)

One-way from

$103
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$280 or less

Good one-way deal

$150 or less
From Illinois to Puerto Rico
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One-way flight from Illinois to Puerto Rico
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Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Illinois to Puerto Rico.
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Price to beat on a one-way flight from Illinois to Puerto Rico.
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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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/213:25 pmSTL - SJU
1 stop7h 25mSouthwest
Sat 10/255:45 amSJU - STL
1 stop12h 20mSouthwest
Deal found 7/29$205
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:00 amMLI - SJU
2 stops16h 54mAmerican Airlines
Thu 10/233:00 pmSJU - MLI
1 stop9h 50mAmerican Airlines
Deal found 7/30$215
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:36 pmPIA - SJU
2 stops15h 49mAmerican Airlines
Tue 12/94:15 pmSJU - PIA
1 stop7h 12mAmerican Airlines
Deal found 7/29$215
This Delta deal was found by Cheapflights users on 7/30. 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.
Mon 9/151:26 pmSTL - SJU
1 stop7h 34mDelta
Fri 9/1912:58 pmSJU - STL
1 stop11h 26mDelta
Deal found 7/30$215
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Thu 8/147:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 7/30$224
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:51 amPIA - SJU
1 stop8h 09mUnited Airlines
Thu 11/202:05 amSJU - PIA
2 stops12h 34mUnited Airlines
Deal found 7/31$233
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:51 amMDW - SJU
1 stop7h 27mFrontier
Fri 9/53:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/29$235
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:22 pmSTL - SJU
1 stop17h 37mFrontier
Fri 11/73:59 amSJU - STL
1 stop11h 28mFrontier
Deal found 7/31$239
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:57 pmSTL - SJU
1 stop11h 37mMultiple Airlines
Wed 9/241:59 amSJU - STL
2 stops9h 51mMultiple Airlines
Deal found 7/29$247
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/242:30 pmSTL - SJU
2 stops9h 26mSpirit Airlines
Thu 8/282:11 amSJU - STL
2 stops12h 21mSpirit Airlines
Deal found 7/29$249
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/99:08 amORD - SJU
1 stop10h 21mFrontier
Wed 8/133:29 amSJU - ORD
1 stop12h 58mFrontier
Deal found 7/30$258

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.

Fly from

Illinois

Fly to

Puerto Rico

Route

Depart

Return

Price

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 10/21

3:25 pm-11:50 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Sat 10/25

5:45 am-5:05 pm

1 stop12h 20m

$205

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Sun 10/19

6:00 am-11:54 pm

2 stops16h 54m

San Juan Luis Munoz Marin Intl

Thu 10/23

3:00 pm-11:50 pm

1 stop9h 50m

$215

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 9/15

1:26 pm-10:00 pm

1 stop7h 34m

San Juan Luis Munoz Marin Intl

Fri 9/19

12:58 pm-11:24 pm

1 stop11h 26m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/10

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Thu 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

9:08 am-8:29 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Wed 8/20

8:13 pm-6:41 pm

1 stop23h 28m

$239

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Wed 8/13

5:40 pm-9:04 am

1 stop14h 24m

San Juan Luis Munoz Marin Intl

Sat 8/16

9:30 pm-11:47 pm

1 stop27h 17m

$239

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 9/19

1:57 pm-2:34 am

1 stop11h 37m

San Juan Luis Munoz Marin Intl

Wed 9/24

1:59 am-10:50 am

2 stops9h 51m

$247

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sun 8/24

2:30 pm-12:56 am

2 stops9h 26m

San Juan Luis Munoz Marin Intl

Thu 8/28

2:11 am-1:32 pm

2 stops12h 21m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 48 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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Puerto Rico

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 June is currently the most expensive (average of $339). 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 July 31, 2025.

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 July 31, 2025.

The most flights from USIL to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

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 July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Illinois to Puerto Rico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 American Airlines. According to our data, you can fly for as low as $103. Users have also found prices from $108 and $113 on Delta and Spirit 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

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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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$296FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$333FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$426FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$194Average$566FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$510FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$418FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$352Average$485FlexibilityNo cancel feeOn-time63%

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