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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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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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 febrero 20, 2025.

Round-trip from

$158
(Mytrip)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

April

Average price

$372

Good round-trip deal

$283 or less

Good one-way deal

$170 or less
From Illinois to Puerto Rico
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One-way flight from Illinois to Puerto Rico
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Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 febrero 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/35:47 pmSTL - SJU
1 stop8h 04mFrontier
sáb. 5/109:30 pmSJU - STL
1 stop27h 36mFrontier
Deal found 2/20$158
This CheapOair deal was found by Cheapflights users on 2/19. 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.
mar. 5/135:47 pmSTL - SJU
1 stop8h 04mMultiple Airlines
lun. 5/194:46 pmSJU - STL
1 stop26h 46mMultiple Airlines
Deal found 2/19$165
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/105:05 amORD - SJU
1 stop18h 10mMultiple Airlines
sáb. 3/156:00 amSJU - ORD
Nonstop5h 36mMultiple Airlines
Deal found 2/20$168
This Mytrip deal was found by Cheapflights users on 2/19. 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.
mié. 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
mar. 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/1410:00 amORD - SJU
Nonstop4h 51mSpirit Airlines
vie. 5/304:46 pmSJU - ORD
Nonstop5h 04mSpirit Airlines
Deal found 2/20$169
This Frontier deal was found by Cheapflights users on 2/20. 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.
sáb. 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
jue. 3/135:45 amSJU - ORD
1 stop14h 09mFrontier
Deal found 2/20$171
This CheapOair deal was found by Cheapflights users on 2/19. 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.
mar. 5/137:37 pmSTL - SJU
2 stops28h 34mSpirit Airlines
lun. 5/194:46 pmSJU - STL
1 stop26h 46mSpirit Airlines
Deal found 2/19$185
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/39:20 amORD - BQN
1 stop15h 27mFrontier
dom. 4/612:42 pmBQN - ORD
1 stop21h 02mFrontier
Deal found 2/20$252
This United Airlines deal was found by Cheapflights users on 2/20. 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.
sáb. 5/33:43 pmSTL - SJU
1 stop7h 11mUnited Airlines
mar. 5/61:05 amSJU - STL
2 stops14h 42mUnited Airlines
Deal found 2/20$265
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/1011:30 amORD - SJU
1 stop7h 40mDelta
mié. 3/192:42 pmSJU - ORD
1 stop7h 16mDelta
Deal found 2/20$271
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
mar. 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This American Airlines deal was found by Cheapflights users on 2/19. 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.
lun. 4/146:00 amMLI - SJU
2 stops13h 20mAmerican Airlines
mar. 4/226:21 amSJU - MLI
2 stops16h 28mAmerican Airlines
Deal found 2/19$275

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 febrero 20, 2025.

Fly from

Illinois

Fly to

Puerto Rico

Route

Depart

Return

Price

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

sáb. 5/3

5:47 pm-2:51 am

1 stop8h 04m

San Juan Luis Munoz Marin Intl

sáb. 5/10

9:30 pm-12:06 am

1 stop27h 36m

$158

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

mar. 5/13

5:47 pm-2:51 am

1 stop8h 04m

San Juan Luis Munoz Marin Intl

lun. 5/19

4:46 pm-6:32 pm

1 stop26h 46m

$165

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 3/10

5:05 am-12:15 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

sáb. 3/15

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mié. 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

mar. 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 5/14

10:00 am-3:51 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

vie. 5/30

4:46 pm-8:50 pm

Nonstop5h 04m

$169

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 3/8

1:30 pm-1:40 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

jue. 3/13

5:45 am-6:54 pm

1 stop14h 09m

$171

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

mar. 5/13

7:37 pm-1:11 am

2 stops28h 34m

San Juan Luis Munoz Marin Intl

lun. 5/19

4:46 pm-6:32 pm

1 stop26h 46m

$185

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

jue. 4/3

9:20 am-1:47 am

1 stop15h 27m

Aguadilla Borinquen

dom. 4/6

12:42 pm-8:44 am

1 stop21h 02m

$252

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

sáb. 5/3

3:43 pm-11:54 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

mar. 5/6

1:05 am-2:47 pm

2 stops14h 42m

$265

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 3/10

11:30 am-8:10 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mié. 3/19

2:42 pm-8:58 pm

1 stop7h 16m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 51 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 $363). 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 febrero 20, 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 febrero 20, 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 febrero 20, 2025.
Read through reviews of airlines operating flights from Illinois to Puerto Rico, such as Southwest, Alaska Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $83 and $133 on Spirit Airlines and Delta, 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 $363). 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.
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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$151Average$274FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$609FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$496FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$412FlexibilityNo cancel feeOn-time62%
DeltaCheapest$293Average$450FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$482FlexibilityNo cancel feeOn-time63%
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