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$103+ Cheap flights from Puerto Rico to Illinois

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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Puerto Rico to Illinois

Keep the following information in mind while searching for Puerto Rico to Illinois flight deals. Data was last updated July 31, 2025.

Round-trip from

$205
(Delta)

One-way from

$103
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$273 or less

Good one-way deal

$190 or less
From Puerto Rico to Illinois
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One-way flight from Puerto Rico to Illinois
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Puerto Rico to Illinois.
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Price to beat on a one-way flight from Puerto Rico to Illinois.
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Find flight deals from Puerto Rico to Illinois

Cheapest flights from Puerto Rico to Illinois
Explore the most affordable flight options available from Puerto Rico to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 10/115:30 amSJU - STL
1 stop14h 12mAmerican Airlines
Sun 10/126:00 amSTL - SJU
1 stop16h 59mAmerican Airlines
Deal found 7/30$205
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 9/185:41 pmSJU - STL
1 stop6h 43mDelta
Wed 9/241:26 pmSTL - SJU
1 stop7h 34mDelta
Deal found 7/31$215
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Fri 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Mon 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31$221
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
Wed 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
Sat 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
Sun 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30$242
This Mytrip deal was found by Cheapflights users on 7/30. 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 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
Sat 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30$248
This Frontier deal was found by Cheapflights users on 7/30. 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 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
Fri 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
This Frontier deal was found by Cheapflights users on 7/30. 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.
Thu 9/253:39 amSJU - STL
1 stop10h 23mFrontier
Fri 10/31:57 pmSTL - SJU
1 stop9h 02mFrontier
Deal found 7/30$268
This Booking.com deal was found by Cheapflights users on 7/30. 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.
Wed 8/132:11 amSJU - STL
2 stops12h 21mSpirit Airlines
Mon 8/182:30 pmSTL - SJU
2 stops8h 27mSpirit Airlines
Deal found 7/30$280
This Trip.com deal was found by Cheapflights users on 7/31. 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 8/112:59 amBQN - ORD
1 stop8h 15mMultiple Airlines
Thu 8/215:16 pmORD - BQN
1 stop8h 32mMultiple Airlines
Deal found 7/31$284
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/71:37 amSJU - STL
1 stop9h 15mMultiple Airlines
Mon 8/115:40 pmSTL - SJU
1 stop7h 59mMultiple Airlines
Deal found 7/30$290

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Illinois 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 July 31, 2025.
Use the filters below to find and compare flights from Puerto Rico to Illinois that are best for you.

Fly from

Puerto Rico

Fly to

Illinois

Route

Depart

Return

Price

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Sat 10/11

5:30 am-6:42 pm

1 stop14h 12m

Lambert-St Louis

Sun 10/12

6:00 am-11:59 pm

1 stop16h 59m

$205

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 9/18

5:41 pm-11:24 pm

1 stop6h 43m

Lambert-St Louis

Wed 9/24

1:26 pm-10:00 pm

1 stop7h 34m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$221

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

Wed 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/13

3:29 am-3:27 pm

1 stop12h 58m

Chicago O'Hare Intl

Sun 8/17

6:56 am-3:10 pm

1 stop7h 14m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/12

3:40 am-10:14 am

1 stop7h 34m

Chicago O'Hare Intl

Sat 9/13

8:00 am-8:02 am

1 stop23h 02m

$248

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 9/25

3:39 am-1:02 pm

1 stop10h 23m

Lambert-St Louis

Fri 10/3

1:57 pm-11:59 pm

1 stop9h 02m

$268

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 8/13

2:11 am-1:32 pm

2 stops12h 21m

Lambert-St Louis

Mon 8/18

2:30 pm-11:57 pm

2 stops8h 27m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 37 results
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Best time to book a flight from Puerto Rico to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Puerto Rico 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 Puerto Rico to Illinois

What is the cheapest month to book a flight from Puerto Rico to Illinois?

Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $245). Flying from Puerto Rico to Illinois in March is currently the most expensive (average of $321). 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 PR to IL?

Find hourly flight availability from Puerto Rico to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

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

Weekly flight availability from Puerto Rico to Illinois

Explore weekly flight availability from Puerto Rico to Illinois. 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 July 31, 2025.

The most flights from PR0 to USIL 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 (8 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Puerto Rico to Illinois. 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 Puerto Rico to Illinois one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $103. Users have also found prices from $104 and $108 on Spirit Airlines and Delta, respectively.

  • Can I find deals for flights from Puerto Rico to Illinois that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Illinois.

  • Can I find deals for business class flights from Puerto Rico to Illinois?

    Yes. Cheapflights offers flight deals from Puerto Rico to Illinois 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 Puerto Rico to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $245). Flying from Puerto Rico to Illinois in March is currently the most expensive (average of $321). 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 Puerto Rico to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Puerto Rico to Illinois

Discover the top 6 airlines that operate flights from Puerto Rico to Illinois. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$246FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$272FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$374FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$483FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$445FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$479FlexibilityNo cancel feeOn-time71%

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