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$108+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$181
(Cheapflightsfares)

One-way from

$108
(Southwest)

Popular in

August

Cheapest in

January

Average price

$297

Good round-trip deal

$339 or less

Good one-way deal

$174 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. 3% potential increase in price ($11 potential increase over avg. RT price).
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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 September 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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Sat 10/119:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Fri 10/177:51 pmORD - SJU
1 stop17h 21mSpirit Airlines
Deal found 9/13$181
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Thu 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$186
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Fri 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/13$187
This eDestinos deal was found by Cheapflights users on 9/12. 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.
Fri 9/263:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Tue 9/306:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Deal found 9/12$190
This eDestinos deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Sun 9/2812:55 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/13$195
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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.
Mon 10/277:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/12$196
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Wed 10/16:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/13$201
This eDestinos deal was found by Cheapflights users on 9/13. 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.
Thu 9/253:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Wed 10/16:30 amORD - SJU
1 stop13h 26mSpirit Airlines
Deal found 9/13$203
This Frontier deal was found by Cheapflights users on 9/13. 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 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/13$207
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sun 10/266:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/13$208
This Delta deal was found by Cheapflights users on 9/14. 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 10/245:43 pmSJU - STL
1 stop6h 58mDelta
Mon 10/276:00 amSTL - SJU
1 stop9h 33mDelta
Deal found 9/14$225
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/235:50 amSJU - MDW
2 stops8h 30mSouthwest
Mon 10/278:45 pmMDW - SJU
1 stop12h 10mSouthwest
Deal found 9/14$227

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 September 15, 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 JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 11/14

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Mon 11/17

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Mon 10/27

2:20 pm-8:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 9/26

7:40 pm-11:56 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 9/28

12:55 pm-6:34 pm

Nonstop4h 39m

$222

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

3:46 pm-11:10 pm

1 stop9h 24m

Chicago O'Hare Intl

Sun 11/9

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Sat 11/15

4:50 pm-11:22 pm

1 stop8h 32m

Lambert-St Louis

Tue 11/18

11:44 am-11:13 pm

1 stop9h 29m

$225

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 10/23

7:15 am-3:55 pm

1 stop9h 40m

Lambert-St Louis

Sat 10/25

6:00 am-2:11 pm

1 stop7h 11m

$225

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

Fri 10/17

4:35 pm-11:50 pm

1 stop6h 15m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

Wed 10/29

9:15 am-8:45 pm

1 stop10h 30m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/30

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

Sun 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

7:00 am-4:25 pm

1 stop8h 25m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 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 September 15, 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 September 15, 2025.

The most flights from PR0 to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 15, 2025.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest, United Airlines, and American 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
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Puerto Rico to Illinois?

    A quick flight from Puerto Rico to Illinois can take about 5h 16m. United Airlines provides one of the quickest options available for as low as $222. The distance from Puerto Rico to Illinois is about 2073 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Puerto Rico to Illinois one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $108. Users have also found prices from $113 and $113 on American Airlines and United Airlines, 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$278FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$246FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$390FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$499FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$478FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$481FlexibilityNo cancel feeOn-time71%

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