Puerto Rico

$64+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 27 — Jan 31
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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 December 22, 2024.

Round-trip from

$162
(Kiwi.com)

One-way from

$64
(Frontier)
From Illinois to Puerto Rico
One-way flight from Illinois to Puerto Rico

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 December 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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.
Mon 12/309:35 pmORD - SJU
1 stop15h 44mSpirit Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/21$244
This eDestinos deal was found by Cheapflights users on 12/21. 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.
Mon 12/309:35 pmORD - SJU
1 stop15h 44mMultiple Airlines
Tue 1/148:45 amSJU - ORD
2 stops29h 02mMultiple Airlines
Deal found 12/21$330
This FlightHub deal was found by Cheapflights users on 12/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/313:53 pmSTL - SJU
1 stop8h 56mMultiple Airlines
Wed 1/88:21 pmSJU - STL
1 stop20h 22mMultiple Airlines
Deal found 12/22$376
This FlightHub deal was found by Cheapflights users on 12/21. 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 12/317:35 amMDW - SJU
1 stop8h 29mFrontier
Tue 12/318:10 pmSJU - MDW
1 stop14h 11mFrontier
Deal found 12/21$395
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/235:45 pmSTL - SJU
1 stop25h 11mFrontier
Thu 12/268:00 amSJU - STL
1 stop13h 20mFrontier
Deal found 12/22$418
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/257:00 amORD - SJU
1 stop14h 10mAmerican Airlines
Fri 12/2712:51 pmSJU - ORD
1 stop11h 01mAmerican Airlines
Deal found 12/21$424
This FlightHub deal was found by Cheapflights users on 12/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/262:19 pmORD - SJU
1 stop8h 22mFrontier
Mon 12/304:00 pmSJU - ORD
1 stop29h 14mFrontier
Deal found 12/22$455
This United deal was found by Cheapflights users on 12/22. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/302:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Fri 1/172:05 amSJU - ORD
1 stop9h 23mUnited Airlines
Deal found 12/22$458
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2710:59 amORD - BQN
1 stop13h 44mFrontier
Sun 12/293:43 amBQN - ORD
1 stop8h 11mFrontier
Deal found 12/21$489
This Mytrip deal was found by Cheapflights users on 12/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:27 pmSTL - SJU
2 stops31h 32mSpirit Airlines
Sat 1/42:32 amSJU - STL
2 stops14h 49mSpirit Airlines
Deal found 12/21$500
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/255:05 amEVV - SJU
1 stop16h 05mAmerican Airlines
Sun 12/295:18 amSJU - EVV
2 stops11h 18mAmerican Airlines
Deal found 12/21$550
This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:20 amMDW - SJU
1 stop28h 35mMultiple Airlines
Tue 12/312:45 amSJU - MDW
1 stop12h 39mMultiple Airlines
Deal found 12/21$557

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/11

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Fri 1/17

9:26 pm-12:51 am

Nonstop5h 25m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/19

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Sun 1/26

6:30 am-1:55 pm

1 stop9h 25m

$163

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/24

5:30 am-12:44 am

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Thu 1/30

4:51 pm-2:42 pm

1 stop23h 51m

$165

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 1/19

4:18 pm-2:46 am

1 stop8h 28m

Aguadilla Borinquen

Sat 1/25

3:51 am-9:52 am

1 stop8h 01m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/20

5:28 pm-2:19 am

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Sun 1/26

6:30 am-1:55 pm

1 stop9h 25m

$177

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/25

7:30 am-9:21 am

2 stops23h 51m

San Juan Luis Munoz Marin Intl

Sat 2/1

8:00 am-11:29 pm

2 stops17h 29m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/19

2:50 pm-11:37 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Thu 3/27

5:00 am-12:02 pm

1 stop8h 02m

$234

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 2/21

5:20 pm-9:35 am

1 stop14h 15m

San Juan Luis Munoz Marin Intl

Sun 2/23

3:54 am-11:43 pm

1 stop21h 49m

$247

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 2/1

11:30 am-12:36 am

2 stops11h 06m

San Juan Luis Munoz Marin Intl

Tue 2/4

2:05 am-2:14 pm

2 stops14h 09m

$254

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/12

11:15 am-10:22 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Mon 1/13

2:05 am-9:40 am

1 stop9h 35m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 52 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 $380). 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 December 22, 2024.

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 December 22, 2024.

The most flights from USIL to PR0 are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 December 22, 2024.
Read through reviews of airlines operating flights from Illinois to Puerto Rico, such as Delta, American Airlines and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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.

8.0
Very good
9,537 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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.

7.4
Good
3,265 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

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 $64. Users have also found prices from $91 and $113 on Spirit 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 March is currently the most expensive (average of $380). 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

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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.

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$293FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$291FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$495FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$463FlexibilityNo cancel feeOn-time63%
DeltaCheapest$307Average$500FlexibilityNo cancel feeOn-timeN/A
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