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Puerto Rico

$126+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
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 June 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Tue 8/257:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/21$257
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/248:57 pm
SJU
-
ORD
1 stop27h 11m
Frontier
Deal found 6/21$258
This Frontier deal was found by Cheapflights users on 6/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/21$259
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 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
Fri 8/217:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/21$260
This Delta deal was found by Cheapflights users on 6/22. 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.
Thu 8/279:54 am
ORD
-
SJU
1 stop11h 35m
Delta
Wed 9/91:21 pm
SJU
-
ORD
1 stop9h 16m
Delta
Deal found 6/22$261
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 8/156:59 am
ORD
-
SJU
1 stop13h 56m
American Airlines
Fri 8/2812:55 am
SJU
-
ORD
Nonstop5h 05m
American Airlines
Deal found 6/21$262
This Frontier deal was found by Cheapflights users on 6/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/20$263
This Super.com deal was found by Cheapflights users on 6/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 8/127:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/21$264
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com 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 8/248:57 pm
SJU
-
ORD
1 stop27h 11m
Frontier
Deal found 6/21$265
This Delta deal was found by Cheapflights users on 6/23. 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 8/228:05 am
ORD
-
SJU
1 stop7h 33m
Delta
Mon 8/317:00 am
SJU
-
ORD
1 stop10h 51m
Delta
Deal found 6/23$266
This Southwest deal was found by Cheapflights users on 6/22. 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 8/227:05 am
MDW
-
SJU
1 stop10h 10m
Southwest
Sun 8/309:25 pm
SJU
-
MDW
1 stop12h 20m
Southwest
Deal found 6/22$266
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 8/275:20 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
-
ORD
1 stop11h 57m
American Airlines
Deal found 6/21$267

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 June 24, 2026.

Round-trip from

$257
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$460

Good round-trip deal

$376 or less

Good one-way deal

$204 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. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 24, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/22

1:50 pm-10:29 pm

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Sat 8/29

2:31 pm-8:30 pm

1 stop6h 59m

$266

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/27

9:54 am-10:29 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Sat 8/29

2:31 pm-8:30 pm

1 stop6h 59m

$266

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/22

5:30 am-4:38 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Fri 9/4

12:56 pm-11:57 pm

1 stop12h 01m

$276

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/27

11:23 am-10:29 pm

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Fri 9/4

12:56 pm-11:57 pm

1 stop12h 01m

$276
Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/29

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Tue 9/1

3:56 pm-8:05 pm

Nonstop5h 09m

$327

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 9/6

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Tue 9/15

3:56 pm-8:05 pm

Nonstop5h 09m

$332

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 9/11

12:55 pm-10:10 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Mon 9/14

5:00 am-10:40 am

1 stop6h 40m

$336

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Wed 9/2

6:00 am-4:38 pm

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Wed 9/9

7:00 am-12:32 pm

1 stop6h 32m

$336

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/15

7:05 am-6:15 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Tue 8/18

5:15 am-12:05 pm

1 stop7h 50m

$346

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/29

6:05 am-4:38 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Tue 9/1

2:59 pm-10:36 pm

1 stop8h 37m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

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

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

Currently, April is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $314). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $633). 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 June 24, 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 34% versus a flight in the morning.

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 June 24, 2026.

The most flights from USIL to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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

Booking 90 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 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 June 20, 2026.

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

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 4h 49m. Fly via Delta, United Airlines, or Southwest 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 JetBlue. According to our data, you can fly for as low as $67. Users have also found prices from $84 and $123 on Frontier and Southwest, 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, April is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $314). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $633). 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 6 airlines flying from Illinois to Puerto Rico

Discover the top 6 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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$325FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$448FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$261Average$519FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$295Average$591FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$352Average$486FlexibilityNo cancel feeOn-time63%

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