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$87+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:26 am
SJU
-
ORD
1 stop8h 59m
JetBlue
Tue 3/246:45 am
ORD
-
SJU
1 stop9h 38m
JetBlue
Deal found 1/27$151
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/71:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Wed 2/2512:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28$161
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 pm
SJU
-
ORD
1 stop24h 27m
Multiple Airlines
Tue 3/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/26$163
This SmartFares deal was found by Cheapflights users on 1/27. 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.
Thu 3/55:01 am
SJU
-
ORD
1 stop8h 48m
JetBlue
Mon 3/912:41 pm
ORD
-
SJU
1 stop7h 43m
JetBlue
Deal found 1/27$167
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 2/51:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Tue 2/1012:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/27$168
This Expedia deal was found by Cheapflights users on 1/26. 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.
Tue 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Tue 3/312:41 pm
ORD
-
SJU
1 stop9h 48m
JetBlue
Deal found 1/26$171
This FlightHub deal was found by Cheapflights users on 1/28. 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.
Wed 2/41:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/88:43 pm
ORD
-
SJU
1 stop16h 52m
Spirit Airlines
Deal found 1/28$175
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 2/61:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Mon 2/912:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/27$176
This Frontier deal was found by Cheapflights users on 1/27. 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.
Tue 2/173:53 am
SJU
-
ORD
1 stop13h 59m
Frontier
Mon 2/2310:15 am
ORD
-
SJU
1 stop13h 09m
Frontier
Deal found 1/27$178
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Wed 2/185:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Mon 2/239:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/27$190
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:59 am
BQN
-
ORD
1 stop13h 53m
Frontier
Tue 3/38:30 am
ORD
-
BQN
1 stop16h 27m
Frontier
Deal found 1/26$199
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:36 pm
SJU
-
STL
1 stop8h 57m
Frontier
Tue 2/103:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Deal found 1/26$203

Find 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 January 29, 2026.

Round-trip from

$151
(JetBlue)

One-way from

$87
(Frontier)

Popular in

December

Cheapest in

February

Average price

$301

Good round-trip deal

$261 or less

Good one-way deal

$205 or less
From Puerto Rico to Illinois
Search Deals
One-way flight from Puerto Rico to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Illinois.
Search Deals
Price to beat on a one-way flight from Puerto Rico to Illinois.
Search Deals

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 January 29, 2026.
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

Wed 3/18

3:26 am-11:25 am

1 stop8h 59m

Chicago O'Hare Intl

Tue 3/24

12:20 pm-8:26 pm

1 stop7h 06m

$171

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

1:44 pm-10:59 pm

1 stop11h 15m

Chicago O'Hare Intl

Mon 3/2

12:41 pm-12:29 am

1 stop9h 48m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/12

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Mon 2/16

12:17 pm-6:49 pm

Nonstop4h 32m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/7

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/11

12:22 pm-5:54 pm

Nonstop4h 32m

$198

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/6

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Wed 5/13

12:22 pm-5:54 pm

Nonstop4h 32m

$198

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 2/23

3:59 am-3:52 pm

1 stop13h 53m

Chicago O'Hare Intl

Tue 3/3

8:30 am-2:57 am

1 stop16h 27m

$199

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/19

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 2/22

5:15 am-3:31 pm

1 stop8h 16m

$202

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/15

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Fri 5/29

3:15 pm-1:59 am

1 stop9h 44m

$203

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/22

11:07 am-6:15 pm

1 stop8h 08m

Chicago O'Hare Intl

Sat 4/25

12:22 pm-5:54 pm

Nonstop4h 32m

$204

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/8

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Mon 5/11

8:31 am-6:30 pm

1 stop8h 59m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, January is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $111). Flying from Puerto Rico to Illinois in December is currently the most expensive (average of $157). 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 January 29, 2026.

When flying from Puerto Rico to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 53% versus a flight in the afternoon.

What is the cheapest day to fly from Puerto Rico to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Illinois. Price data was last updated on February 10, 2025.

Travelers seeking maximum savings on their Puerto Rico to Illinois flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 29, 2026.

The most flights from PR0 to USIL are scheduled on a Wednesday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 January 29, 2026.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as United Airlines, American Airlines, and JetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,206 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.2
Good
2,891 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,394 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.7
Fair
3,056 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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. JetBlue provides one of the quickest options available for as low as $187. 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 JetBlue. According to our data, you can fly for as low as $74. Users have also found prices from $92 and $94 on Frontier and Spirit 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, January is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $111). Flying from Puerto Rico to Illinois in December is currently the most expensive (average of $157). 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 Puerto Rico to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Puerto Rico to Illinois

Discover the top 7 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$538FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$118Average$270FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$480FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$469FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$419Average$559FlexibilityNo cancel feeOn-time63%

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