HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$95+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 22, 2025.

Round-trip from

$189
(eDestinos)

One-way from

$95
(eDestinos)

Popular in

December

Cheapest in

August

Average price

$352

Good round-trip deal

$337 or less

Good one-way deal

$186 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. 15% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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

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 April 22, 2025.

This eDestinos deal was found by Cheapflights users on 4/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1111:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Thu 5/156:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 4/21$189
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 10/411:51 amSTL - SJU
1 stop9h 17mDelta
Sat 10/112:15 pmSJU - STL
1 stop7h 20mDelta
Deal found 4/22$245
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/34:15 pmORD - SJU
1 stop9h 36mMultiple Airlines
Sat 5/108:12 pmSJU - ORD
1 stop13h 38mMultiple Airlines
Deal found 4/22$248
This Trip.com deal was found by Cheapflights users on 4/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/295:41 pmSTL - SJU
1 stop8h 08mFrontier
Mon 5/53:56 amSJU - STL
1 stop21h 10mFrontier
Deal found 4/22$286
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/295:41 pmSTL - SJU
1 stop8h 08mMultiple Airlines
Tue 5/69:25 amSJU - STL
1 stop8h 50mMultiple Airlines
Deal found 4/22$289
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/16:00 amSTL - SJU
1 stop15h 30mAmerican Airlines
Wed 6/47:15 amSJU - STL
1 stop15h 11mAmerican Airlines
Deal found 4/22$290
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/29:00 amORD - SJU
1 stop8h 47mFrontier
Mon 5/56:00 amSJU - ORD
1 stop13h 29mFrontier
Deal found 4/22$298
This Frontier deal was found by Cheapflights users on 4/21. 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.
Mon 5/56:15 amMDW - SJU
1 stop7h 32mFrontier
Wed 5/73:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/21$298
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/34:15 pmORD - PSE
1 stop15h 41mFrontier
Thu 5/89:46 amPSE - ORD
1 stop14h 46mFrontier
Deal found 4/21$299
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/284:30 pmORD - BQN
1 stop8h 24mFrontier
Fri 5/29:56 amBQN - ORD
1 stop14h 36mFrontier
Deal found 4/21$299
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amORD - SJU
1 stop9h 50mDelta
Fri 9/122:28 pmSJU - ORD
1 stop10h 25mDelta
Deal found 4/21$307
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:31 pmMLI - SJU
2 stops17h 44mAmerican Airlines
Mon 10/206:30 amSJU - MLI
2 stops16h 18mAmerican Airlines
Deal found 4/22$317

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 April 22, 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

Sun 5/11

11:30 am-5:16 pm

Nonstop4h 46m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:09 am-10:25 am

Nonstop5h 16m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/3

4:15 pm-2:51 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Sat 5/10

8:12 pm-8:50 am

1 stop13h 38m

$248

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 7/15

6:00 am-1:29 pm

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Wed 7/23

2:15 pm-8:30 pm

1 stop7h 15m

$281

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/29

5:41 pm-2:49 am

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Mon 5/5

3:56 am-12:06 am

1 stop21h 10m

$286

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/29

5:41 pm-2:49 am

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Tue 5/6

9:25 am-5:15 pm

1 stop8h 50m

$289

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sun 6/1

6:00 am-10:30 pm

1 stop15h 30m

San Juan Luis Munoz Marin Intl

Wed 6/4

7:15 am-9:26 pm

1 stop15h 11m

$290

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/2

9:00 am-6:47 pm

1 stop8h 47m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

$298

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/5

6:15 am-2:47 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-12:24 pm

1 stop9h 28m

$298

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 5/3

4:15 pm-8:56 am

1 stop15h 41m

Ponce Mercedita

Thu 5/8

9:46 am-11:32 pm

1 stop14h 46m

$299

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 5/3

4:15 pm-1:57 am

1 stop8h 42m

Aguadilla Borinquen

Thu 5/8

2:47 am-11:32 pm

1 stop21h 45m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 56 results
1
2
3
...
6

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 $254). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $336). 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 April 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Puerto Rico as you normally would.

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 April 22, 2025.

The most flights from USIL to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated April 22, 2025.
Read through reviews of airlines operating flights from Illinois to Puerto Rico, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $95. Users have also found prices from $105 and $123 on American Airlines and United 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 $254). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $336). 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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Punta Cana flights
Orlando to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
Newark to Santiago de los Caballeros flights
LaGuardia to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Newark to Santo Domingo flights
John F Kennedy Intl to Montego Bay flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
John F Kennedy Intl to Oranjestad flights
Newark to Oranjestad flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Hobby to Luis Munoz Marin Intl flights
Newark to Nassau flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Kingston flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Nassau flights
Atlanta to Punta Cana flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Bridgetown flights
Dulles Intl to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Boston to Oranjestad flights
Dulles Intl to Montego Bay flights
Newark to Simpson Bay flights
John F Kennedy Intl to Saint Thomas Island flights
O'Hare Intl to Punta Cana flights
Philadelphia to Punta Cana flights
Boston to Punta Cana flights
Dallas/Fort Worth to Punta Cana flights
LaGuardia to Oranjestad flights
Dulles Intl to Oranjestad flights
Raleigh to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$306FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$277FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$539FlexibilityNo cancel feeOn-time71%
DeltaCheapest$222Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$493FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$404FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$343Average$479FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.