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$65+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Illinois to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Puerto Rico (PR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$147
(Priceline)

One-way from

$65
(Frontier)

Good round-trip deal

$295 or less

Good one-way deal

$207 or less
From Illinois to Puerto Rico
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One-way flight from Illinois to Puerto Rico
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Price to beat on a round-trip flight from Illinois to Puerto Rico.
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Price to beat on a one-way flight from Illinois to Puerto Rico.
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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 January 21, 2025.

This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/228:44 pmORD - PSE
1 stop13h 09mFrontier
Tue 2/2512:53 pmPSE - ORD
1 stop22h 34mFrontier
Deal found 1/20$147
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/2512:21 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Thu 3/67:00 amSJU - ORD
Nonstop5h 36mSpirit Airlines
Deal found 1/21$160
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:36 pmMDW - SJU
1 stop8h 18mFrontier
Mon 4/75:01 amSJU - MDW
1 stop15h 45mFrontier
Deal found 1/21$160
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/43:14 pmORD - SJU
1 stop16h 35mMultiple Airlines
Wed 3/125:45 pmSJU - ORD
1 stop7h 22mMultiple Airlines
Deal found 1/20$161
This Frontier deal was found by Cheapflights users on 1/21. 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.
Fri 2/217:18 pmORD - SJU
1 stop12h 31mFrontier
Tue 2/259:30 pmSJU - ORD
1 stop13h 57mFrontier
Deal found 1/21$170
This CheapOair deal was found by Cheapflights users on 1/21. 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 2/85:05 pmSTL - SJU
1 stop19h 43mFrontier
Thu 2/1310:31 pmSJU - STL
1 stop27h 12mFrontier
Deal found 1/21$174
This Booking.com deal was found by Cheapflights users on 1/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/175:07 pmORD - BQN
1 stop7h 50mFrontier
Fri 4/252:47 amBQN - ORD
1 stop21h 52mFrontier
Deal found 1/21$180
This CheapOair deal was found by Cheapflights users on 1/21. 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.
Tue 2/184:00 pmSTL - SJU
1 stop29h 22mMultiple Airlines
Mon 2/243:49 amSJU - STL
1 stop21h 54mMultiple Airlines
Deal found 1/21$190
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/44:00 pmSTL - SJU
1 stop6h 27mSpirit Airlines
Sun 3/93:38 amSJU - STL
2 stops38h 04mSpirit Airlines
Deal found 1/20$221
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
Fri 2/71:45 pmSJU - MDW
1 stop10h 15mSouthwest
Deal found 1/20$235
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/210:35 amORD - SJU
1 stop8h 53mUnited Airlines
Wed 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Deal found 1/21$245
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/101:02 pmSTL - SJU
2 stops9h 34mUnited Airlines
Wed 2/122:05 amSJU - STL
2 stops14h 31mUnited Airlines
Deal found 1/20$265

Find flights from Illinois to Puerto Rico within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 2/22

8:44 pm-11:53 am

1 stop13h 09m

Ponce Mercedita

Tue 2/25

12:53 pm-9:27 am

1 stop22h 34m

$147

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/25

12:21 pm-6:52 pm

Nonstop4h 31m

San Juan Luis Munoz Marin Intl

Thu 3/6

7:00 am-10:36 am

Nonstop5h 36m

$160

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 4/1

2:36 pm-11:54 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Mon 4/7

5:01 am-7:46 pm

1 stop15h 45m

$160

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/4

3:14 pm-9:49 am

1 stop16h 35m

San Juan Luis Munoz Marin Intl

Wed 3/12

5:45 pm-12:07 am

1 stop7h 22m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/21

7:18 pm-9:49 am

1 stop12h 31m

San Juan Luis Munoz Marin Intl

Tue 2/25

9:30 pm-9:27 am

1 stop13h 57m

$170

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 2/8

5:05 pm-2:48 pm

1 stop19h 43m

San Juan Luis Munoz Marin Intl

Thu 2/13

10:31 pm-11:43 pm

1 stop27h 12m

$174

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 4/17

5:07 pm-1:57 am

1 stop7h 50m

Aguadilla Borinquen

Fri 4/25

9:56 am-11:39 pm

1 stop14h 43m

$180

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 2/18

4:00 pm-11:22 pm

1 stop29h 22m

San Juan Luis Munoz Marin Intl

Mon 2/24

3:49 am-11:43 pm

1 stop21h 54m

$190

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 3/4

4:00 pm-12:27 am

1 stop6h 27m

San Juan Luis Munoz Marin Intl

Sun 3/9

3:38 am-4:42 pm

2 stops38h 04m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Fri 2/7

1:45 pm-10:00 pm

1 stop10h 15m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 57 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.

Travel insights for flights from Illinois to Puerto Rico

Get recent, data-driven insights about flights from Illinois to Puerto Rico including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 21, 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 January 21, 2025.

The most flights from USIL to PR0 are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 January 21, 2025.
Read through reviews of airlines operating flights from Illinois to Puerto Rico, such as Spirit Airlines, Frontier and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $82 and $118 on Spirit Airlines 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, 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 March is currently the most expensive (average of $378). 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.

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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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O'Hare Intl to Montego Bay flights
Miami to Santo Domingo flights
LaGuardia to Montego Bay 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$301FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$155Average$279FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$584FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$496FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$274Average$399FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$317Average$474FlexibilityNo cancel feeOn-time63%
DeltaCheapest$324Average$490FlexibilityNo cancel feeOn-timeN/A
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