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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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/2712:55 pmORD - SJU
1 stop11h 59mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/28$212
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
Thu 11/274:05 pmSJU - ORD
1 stop10h 03mFrontier
Deal found 10/29$215
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/58:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 10/28$217
This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 10/27$218
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2511:48 amORD - SJU
1 stop9h 56mMultiple Airlines
Thu 11/274:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/28$219
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/176:40 amORD - SJU
2 stops30h 02mMultiple Airlines
Fri 11/215:19 pmSJU - ORD
1 stop17h 58mMultiple Airlines
Deal found 10/27$220
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1810:00 amSTL - SJU
2 stops10h 22mUnited Airlines
Tue 11/182:05 amSJU - STL
1 stop10h 35mUnited Airlines
Deal found 10/28$220
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/274:00 pmMDW - SJU
2 stops39h 27mFrontier
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/178:00 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 11/209:30 pmSJU - ORD
1 stop15h 05mMultiple Airlines
Deal found 10/27$222
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/82:20 pmORD - SJU
Nonstop4h 40mUnited Airlines
Wed 12/102:05 amSJU - ORD
1 stop9h 43mUnited Airlines
Deal found 10/28$223
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:40 amORD - SJU
1 stop9h 14mFrontier
Fri 11/212:25 amSJU - ORD
1 stop10h 46mFrontier
Deal found 10/28$225
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1810:00 amSTL - SJU
2 stops10h 22mUnited Airlines
Thu 11/208:10 amSJU - STL
1 stop9h 36mUnited Airlines
Deal found 10/27$225

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 October 29, 2025.

Round-trip from

$209
(Frontier)

One-way from

$109
(Travelocity)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$350 or less

Good one-way deal

$198 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. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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.
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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 October 29, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:35 am-11:57 am

Nonstop5h 22m

$218

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 1/20

9:57 am-9:00 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:46 pm-10:00 pm

1 stop8h 14m

$225

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

5:33 am-2:30 pm

1 stop6h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

1:55 pm-11:59 pm

1 stop8h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:27 pm-11:57 pm

1 stop7h 30m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:10 am-2:25 pm

1 stop8h 15m

$227

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 11/13

5:25 am-3:04 am

1 stop19h 39m

Aguadilla Borinquen

Wed 11/19

3:55 am-7:26 am

1 stop29h 31m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/4

9:52 am-8:57 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:00 am-5:37 pm

1 stop12h 37m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:26 pm

1 stop8h 31m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:05 am-9:40 am

1 stop9h 35m

$258

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Mon 1/26

8:50 am-9:39 pm

1 stop10h 49m

San Juan Luis Munoz Marin Intl

Sat 1/31

6:00 am-10:16 pm

2 stops18h 16m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, February 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 $188). 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 October 29, 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 56% 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 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 40m. Fly via United Airlines, Delta, or Frontier 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 United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $113 and $114 on Delta 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, February 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 $188). 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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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$317FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$406FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$577FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$273Average$510FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$380Average$490FlexibilityNo cancel feeOn-time63%

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