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Puerto Rico

$87+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Frontier deal was found by Cheapflights users on 1/27. 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 2/213:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Wed 3/411:07 am
SJU
-
STL
1 stop13h 20m
Frontier
Deal found 1/27$178
This Frontier deal was found by Cheapflights users on 1/27. 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 2/233:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Wed 3/411:07 am
SJU
-
STL
1 stop13h 20m
Frontier
Deal found 1/27$182
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Tue 2/310:48 am
ORD
-
SJU
1 stop10h 45m
Spirit Airlines
Tue 2/101:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Deal found 1/27$185
This Priceline deal was found by Cheapflights users on 1/27. 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.
Tue 3/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Sat 3/712:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$186
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
Wed 3/1111:32 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Multiple Airlines
Fri 3/66:50 pm
SJU
-
ORD
1 stop17h 03m
Multiple Airlines
Deal found 1/28$188
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/28$189
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 2/233:50 pm
ORD
-
SJU
1 stop6h 53m
Multiple Airlines
Mon 3/911:32 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/27$190
This JetBlue deal was found by Cheapflights users on 1/27. 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.
Mon 2/2310:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Tue 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Deal found 1/27$191
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 4/205:01 am
ORD
-
SJU
1 stop8h 07m
Multiple Airlines
Sat 4/2512:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/28$192
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Tue 2/243:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Mon 3/23:53 am
SJU
-
STL
1 stop20h 34m
Frontier
Deal found 1/28$192
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Tue 3/2411:13 am
SJU
-
ORD
Nonstop5h 27m
Spirit Airlines
Deal found 1/29$193

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 January 29, 2026.

Round-trip from

$178
(Frontier)

One-way from

$87
(Priceline)

Popular in

December

Cheapest in

April

Average price

$358

Good round-trip deal

$303 or less

Good one-way deal

$128 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 ($47 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 January 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 January 29, 2026.
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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/11

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Wed 5/13

11:59 pm-9:48 am

1 stop10h 49m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/9

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Fri 5/15

11:59 pm-9:48 am

1 stop10h 49m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/9

12:41 pm-11:29 pm

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Mon 3/16

3:26 am-11:25 am

1 stop8h 59m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:10 am-12:04 pm

1 stop8h 54m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/10

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/12

12:20 pm-8:26 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Mon 3/23

3:26 am-11:25 am

1 stop8h 59m

$221

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 3/3

8:30 am-2:57 am

1 stop16h 27m

Aguadilla Borinquen

Mon 3/16

2:42 am-11:38 pm

1 stop21h 56m

$225

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/19

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Fri 5/29

7:40 am-11:53 am

Nonstop5h 13m

$237

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 3/30

7:03 am-4:18 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Sat 4/4

5:30 pm-11:58 pm

1 stop7h 28m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 $126). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $224). 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 January 29, 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 31% 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 February 10, 2025.

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. 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 January 29, 2026.

The most flights from USIL to PR0 are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, 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 8h 15m. Fly via JetBlue, Frontier, or Delta to get the fastest option. Illinois and Puerto Rico are separated by a distance of 2024 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 $74 and $87 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, September is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $126). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $224). 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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
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Boston to Oranjestad flights
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LaGuardia to Punta Cana flights
Dulles Intl to Punta Cana flights
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Newark to Nassau flights
John F Kennedy Intl to Simpson Bay flights
Hobby to Luis Munoz Marin Intl flights
Detroit to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Midway to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
LaGuardia to Nassau flights
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O'Hare Intl to Punta Cana flights
John F Kennedy Intl to Saint Thomas Island flights
LaGuardia to Oranjestad flights
LaGuardia to Santo Domingo flights
John F Kennedy Intl to Providenciales flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Atlanta to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
Denver to Luis Munoz Marin Intl flights
Baltimore to Punta Cana 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$292FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$244FlexibilityNo cancel feeOn-time62%
DeltaCheapest$136Average$400FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$137Average$271FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$225Average$593FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$252Average$507FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%

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