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Puerto Rico

$109+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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Cheap 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 May 12, 2026.

This American Airlines deal was found by Cheapflights users on 5/11. 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 8/235:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Wed 8/267:14 pm
SJU
-
ORD
1 stop14h 46m
American Airlines
Deal found 5/11$222
This Delta deal was found by Cheapflights users on 5/11. 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 8/196:40 am
ORD
-
SJU
1 stop8h 57m
Delta
Wed 9/25:45 pm
SJU
-
ORD
1 stop7h 12m
Delta
Deal found 5/11$226
This Delta deal was found by Cheapflights users on 5/11. 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 8/1910:54 am
MDW
-
SJU
1 stop10h 35m
Delta
Wed 9/22:40 pm
SJU
-
MDW
1 stop8h 06m
Delta
Deal found 5/11$226
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 8/195:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Wed 9/26:51 am
SJU
-
ORD
1 stop8h 24m
American Airlines
Deal found 5/12$227
This Frontier deal was found by Cheapflights users on 5/12. 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.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/12$228
This Priceline deal was found by Cheapflights users on 5/12. 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 9/512:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Thu 9/105:12 pm
SJU
-
ORD
1 stop23h 14m
Frontier
Deal found 5/12$229
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/10$230
This American Airlines deal was found by Cheapflights users on 5/11. 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 8/235:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Sat 8/2910:33 am
SJU
-
ORD
1 stop13h 27m
American Airlines
Deal found 5/11$232
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Thu 8/135:13 pm
ORD
-
SJU
1 stop7h 58m
Frontier
Tue 8/186:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/7$235
This Delta deal was found by Cheapflights users on 5/11. 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.
Sat 8/221:48 pm
ORD
-
SJU
1 stop7h 41m
Delta
Thu 8/275:49 pm
SJU
-
ORD
1 stop7h 09m
Delta
Deal found 5/11$236
This Southwest deal was found by Cheapflights users on 5/8. 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 8/227:50 am
MDW
-
SJU
2 stops7h 50m
Southwest
Wed 8/262:25 pm
SJU
-
MDW
1 stop7h 20m
Southwest
Deal found 5/8$236
This Frontier deal was found by Cheapflights users on 5/10. 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.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/246:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/10$237

Find 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 May 12, 2026.

Round-trip from

$222
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$356

Good round-trip deal

$306 or less

Good one-way deal

$135 or less
From Illinois to Puerto Rico
Search Deals
One-way flight from Illinois to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Puerto Rico.
Search Deals
Price to beat on a one-way flight from Illinois to Puerto Rico.
Search Deals

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 May 12, 2026.
Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Wed 8/5

5:13 pm-9:46 am

1 stop15h 33m

Ponce Mercedita

Wed 8/12

11:42 am-11:05 pm

1 stop12h 23m

$321

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/30

11:05 am-10:29 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Mon 8/3

6:00 am-11:51 am

1 stop6h 51m

$336

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 8/8

6:30 am-6:15 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:05 am-11:05 am

1 stop7h 00m

$390

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Tue 6/9

6:55 am-9:42 am

2 stops49h 47m

Ponce Mercedita

Tue 6/16

10:27 am-8:03 am

2 stops22h 36m

$426

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 7/4

6:30 am-3:11 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Tue 7/21

12:56 pm-11:53 pm

1 stop11h 57m

$426

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 8/4

7:15 am-6:10 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Tue 8/11

8:20 am-4:45 pm

2 stops9h 25m

$443

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 8/3

4:35 pm-11:04 am

2 stops17h 29m

San Juan Luis Munoz Marin Intl

Sun 8/9

7:20 am-9:33 pm

1 stop15h 13m

$449

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 6/28

5:30 am-4:46 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Tue 7/21

2:42 pm-11:53 pm

1 stop10h 11m

$456

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 7/4

8:05 am-1:55 pm

Nonstop4h 50m

San Juan Luis Munoz Marin Intl

Wed 7/8

5:00 am-2:00 pm

1 stop10h 00m

$456

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 7/16

5:13 pm-9:46 am

1 stop15h 33m

Ponce Mercedita

Mon 7/20

10:31 am-11:05 pm

1 stop13h 34m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Illinois to Puerto Rico?

Booking 56 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Puerto Rico. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, May is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $318). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $632). 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 May 12, 2026.

When flying from Illinois to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight in the morning.

What is the cheapest day to fly from Illinois to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Puerto Rico. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Illinois to Puerto Rico flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 12, 2026.

The most flights from USIL to PR0 are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

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.

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

    There are many flights that can get you from Illinois to Puerto Rico in 10h 24m. Fly via Frontier, Delta, or Southwest to get the fastest option. Illinois and Puerto Rico are separated by a distance of 2057 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Illinois to Puerto Rico one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $67. Users have also found prices from $79 and $90 on Frontier 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, May is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $318). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $632). 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.
Newark to Luis Munoz Marin Intl flights
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LaGuardia to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Newark to Simpson Bay flights
LaGuardia to Santiago de los Caballeros flights
Atlanta to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Orlando to Punta Cana flights
Boston to Oranjestad flights
Miami to Luis Munoz Marin Intl flights
Newark to Nassau flights
Baltimore to Punta Cana flights
LaGuardia to Montego Bay flights
Boston to Punta Cana flights
John F Kennedy Intl to Kingston flights
Dallas/Fort Worth to Punta Cana flights
Philadelphia to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
John F Kennedy Intl to Nassau flights

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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$235FlexibilityNo cancel feeOn-time62%
FrontierCheapest$122Average$309FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$387FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$140Average$314FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$225Average$591FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$256Average$515FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$352Average$489FlexibilityNo cancel feeOn-time63%

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