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$77+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$139
(Cheapflightsfares)

One-way from

$77
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$302

Good round-trip deal

$257 or less

Good one-way deal

$171 or less
From Puerto Rico to Illinois
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One-way flight from Puerto Rico to Illinois
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 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 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 February 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:15 pmSJU - ORD
1 stop15h 36mSpirit Airlines
Mon 5/126:00 amORD - SJU
1 stop17h 12mSpirit Airlines
Deal found 2/22$139
This Booking.com deal was found by Cheapflights users on 2/21. 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 5/19:58 pmSJU - ORD
1 stop9h 44mMultiple Airlines
Tue 5/68:04 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 2/21$141
This Frontier deal was found by Cheapflights users on 2/22. 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.
Mon 5/510:46 amSJU - MDW
1 stop14h 01mFrontier
Mon 5/1212:15 pmMDW - SJU
1 stop12h 35mFrontier
Deal found 2/22$150
This Frontier deal was found by Cheapflights users on 2/21. 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 5/26:00 amSJU - ORD
1 stop14h 18mFrontier
Mon 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/21$150
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Thu 4/312:52 pmBQN - ORD
1 stop8h 03mFrontier
Sat 4/127:20 amORD - BQN
1 stop17h 39mFrontier
Deal found 2/21$154
This eDestinos deal was found by Cheapflights users on 2/21. 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 3/162:44 amSJU - STL
1 stop7h 52mFrontier
Mon 3/175:24 pmSTL - SJU
1 stop7h 25mFrontier
Deal found 2/21$155
This Frontier deal was found by Cheapflights users on 2/21. 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.
Thu 4/312:52 pmBQN - MDW
1 stop7h 43mFrontier
Sat 4/1212:58 pmMDW - BQN
1 stop12h 01mFrontier
Deal found 2/21$170
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.
Sat 3/15:20 pmSJU - STL
1 stop8h 23mMultiple Airlines
Tue 3/44:00 pmSTL - SJU
1 stop6h 27mMultiple Airlines
Deal found 2/20$242
This Delta deal was found by Cheapflights users on 2/22. 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.
Fri 5/212:50 pmSJU - MDW
1 stop10h 36mDelta
Sun 5/46:04 amMDW - SJU
1 stop8h 57mDelta
Deal found 2/22$271
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.
Sat 3/16:00 amSJU - STL
2 stops34h 42mSpirit Airlines
Tue 3/44:00 pmSTL - SJU
1 stop6h 27mSpirit Airlines
Deal found 2/20$278
This Delta deal was found by Cheapflights users on 2/21. 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.
Thu 3/277:15 amSJU - STL
1 stop9h 25mDelta
Wed 4/96:00 amSTL - SJU
1 stop8h 03mDelta
Deal found 2/21$314
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Thu 5/227:45 amSJU - STL
1 stop8h 45mUnited Airlines
Tue 5/275:27 pmSTL - SJU
2 stops11h 03mUnited Airlines
Deal found 2/21$365

Find flights from Puerto Rico to Illinois within your budget

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 February 22, 2025.

Fly from

Puerto Rico

Fly to

Illinois

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 5/6

6:15 pm-8:51 am

1 stop15h 36m

Chicago O'Hare Intl

Mon 5/12

6:00 am-12:12 am

1 stop17h 12m

$139

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/1

9:58 pm-6:42 am

1 stop9h 44m

Chicago O'Hare Intl

Tue 5/6

8:04 am-1:45 pm

Nonstop4h 41m

$141

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:47 pm

1 stop14h 01m

Chicago Midway

Mon 5/12

12:15 pm-1:50 am

1 stop12h 35m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

6:00 am-7:18 pm

1 stop14h 18m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

$150

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Thu 4/3

12:52 pm-7:35 pm

1 stop7h 43m

Chicago Midway

Thu 4/10

12:46 pm-1:57 am

1 stop12h 11m

$152

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 4/3

12:52 pm-7:55 pm

1 stop8h 03m

Chicago O'Hare Intl

Sat 4/12

7:20 am-1:59 am

1 stop17h 39m

$154

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Sun 3/16

2:44 am-9:36 am

1 stop7h 52m

Lambert-St Louis

Mon 3/17

5:24 pm-1:49 am

1 stop7h 25m

$155

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/2

12:50 pm-10:26 pm

1 stop10h 36m

Chicago Midway

Sun 5/4

6:04 am-4:01 pm

1 stop8h 57m

$271

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 3/27

7:15 am-3:40 pm

1 stop9h 25m

Lambert-St Louis

Wed 4/9

6:00 am-3:03 pm

1 stop8h 03m

$314

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 5/22

7:45 am-3:30 pm

1 stop8h 45m

Lambert-St Louis

Tue 5/27

5:27 pm-5:30 am

2 stops11h 03m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 41 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.

Travel insights for flights from Puerto Rico to Illinois

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

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 February 22, 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 February 22, 2025.

The most flights from PR0 to USIL are scheduled on a Saturday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Illinois by month

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

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

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

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 22, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Puerto Rico to Illinois. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
3,068 reviews
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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 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 Frontier. According to our data, you can fly for as low as $77. Users have also found prices from $80 and $133 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$376FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$257FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$478FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$556FlexibilityNo cancel feeOn-time71%
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