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Puerto Rico

$58+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
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 December 14, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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.
Tue 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
Tue 1/139:00 amSJU - ORD
1 stop9h 52mFrontier
Deal found 12/14$201
This JetBlue deal was found by Cheapflights users on 12/13. 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.
Sat 12/206:45 amORD - SJU
1 stop10h 04mJetBlue
Sun 12/282:21 pmSJU - ORD
1 stop9h 43mJetBlue
Deal found 12/13$202
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Wed 12/316:05 pmORD - SJU
1 stop12h 34mMultiple Airlines
Tue 1/139:00 amSJU - ORD
1 stop9h 52mMultiple Airlines
Deal found 12/14$203
This Frontier deal was found by Cheapflights users on 12/14. 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.
Wed 12/3111:23 amORD - SJU
1 stop13h 27mFrontier
Thu 1/1511:55 amSJU - ORD
1 stop8h 30mFrontier
Deal found 12/14$205
This Trip.com deal was found by Cheapflights users on 12/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Wed 12/243:55 amSJU - ORD
1 stop8h 23mMultiple Airlines
Deal found 12/12$208
This Priceline deal was found by Cheapflights users on 12/12. 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.
Wed 12/1711:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/12$215
This Trip.com deal was found by Cheapflights users on 12/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Mon 12/229:37 pmSJU - ORD
1 stop22h 14mMultiple Airlines
Deal found 12/12$216
This Trip.com deal was found by Cheapflights users on 12/14. 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 12/157:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/14$217
This Frontier deal was found by Cheapflights users on 12/12. 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.
Mon 12/291:44 pmORD - SJU
1 stop9h 22mFrontier
Tue 1/139:00 amSJU - ORD
1 stop9h 52mFrontier
Deal found 12/12$220
This Priceline deal was found by Cheapflights users on 12/13. 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.
Mon 12/1511:25 amORD - SJU
1 stop10h 57mMultiple Airlines
Sun 12/218:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/13$230
This Priceline deal was found by Cheapflights users on 12/13. 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.
Wed 12/243:32 pmMDW - SJU
1 stop9h 07mFrontier
Wed 1/144:35 pmSJU - MDW
1 stop7h 44mFrontier
Deal found 12/13$240
This Priceline deal was found by Cheapflights users on 12/12. 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.
Mon 12/226:15 amMDW - SJU
1 stop18h 24mFrontier
Thu 12/257:00 amSJU - MDW
1 stop12h 38mFrontier
Deal found 12/12$260

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 December 14, 2025.

Round-trip from

$148
(Priceline)

One-way from

$58
(Priceline)

Popular in

December

Cheapest in

April

Average price

$570

Good round-trip deal

$315 or less

Good one-way deal

$153 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 ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 14, 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

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 3/7

4:18 pm-10:40 am

1 stop16h 22m

Ponce Mercedita

Thu 3/12

11:35 am-3:28 pm

1 stop28h 53m

$180

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

9:40 am-7:26 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Tue 2/3

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 1/8

8:27 pm-11:19 am

1 stop12h 52m

Ponce Mercedita

Thu 1/15

12:14 pm-7:41 pm

1 stop9h 27m

$202

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 2/2

5:42 pm-11:59 pm

1 stop28h 17m

San Juan Luis Munoz Marin Intl

Sun 2/8

6:00 am-11:33 pm

1 stop19h 33m

$204

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sat 2/7

1:30 pm-7:45 pm

1 stop8h 15m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/24

10:00 am-9:56 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:10 am-11:48 am

1 stop8h 38m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/6

7:45 am-6:02 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

1:44 pm-11:10 pm

1 stop11h 26m

$211

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 2/20

9:07 pm-11:25 am

1 stop12h 18m

Ponce Mercedita

Mon 3/2

11:30 am-11:15 pm

1 stop13h 45m

$215

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sun 1/18

5:11 pm-3:03 am

1 stop7h 52m

San Juan Luis Munoz Marin Intl

Sat 1/24

4:36 pm-11:33 pm

1 stop8h 57m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 60 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 $127). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $221). 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 December 14, 2025.

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 50% 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 December 16, 2024.

Travelers seeking maximum savings on their Illinois to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday 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 December 14, 2025.

The most flights from USIL to PR0 are scheduled on a Friday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 7h 46m. Fly via Frontier, JetBlue, or United Airlines to get the fastest option. Illinois and Puerto Rico are separated by a distance of 2073 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 Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $82 and $91 on JetBlue 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 $127). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $221). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
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LaGuardia to Punta Cana flights
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Hartford to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Tampa to Luis Munoz Marin Intl flights
Boston to Oranjestad flights
LaGuardia to Santo Domingo flights
John F Kennedy Intl to Montego Bay flights
Newark to Nassau flights
Fort Lauderdale to Luis Munoz Marin Intl flights
John F Kennedy Intl to Saint Thomas Island flights
Dulles Intl to Punta Cana flights
Orlando to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
Miami to Santo Domingo flights
Boston to Punta Cana flights
Newark to Simpson Bay flights
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Detroit to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Port of Spain flights
John F Kennedy Intl to Nassau flights
Newark to Saint Thomas Island flights
LaGuardia to Oranjestad flights
Midway to Luis Munoz Marin Intl flights
Fort Lauderdale to Santo Domingo flights
Denver to Luis Munoz Marin Intl flights
John F Kennedy Intl to Providenciales 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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$312FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$290FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$147Average$347FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$284Average$528FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$489FlexibilityNo cancel feeOn-time63%

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