How long is the flight from Illinois to Puerto Rico?

There are many flights that can get you from Illinois to Puerto Rico in 4h 40m. Fly via United Airlines, Delta, or Southwest to get the fastest option. Illinois and Puerto Rico are separated by a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $113 and $113 on Delta and Southwest, respectively.

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.

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).

How far in advance should I book a flight from Illinois to Puerto Rico?

Find a great deal and save up to 54% by booking at least 43 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Illinois to Puerto Rico within the next two weeks, with the cheapest ticket starting at $312.

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

Our data shows that October tends to be the cheapest month to fly to Puerto Rico from Illinois. Users have commonly found prices around $402 for the month, but tickets can be as low as $143. Due to multiple factors, prepare for potentially higher prices in December.

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.

$108+ Cheap Flights from Illinois to Puerto Rico

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Cheap flight deals from Illinois to Puerto Rico

Round-trip from	$207 (Mytrip)
One-way from	$108 (Cheapflightsfares)
Popular in	December
Cheapest in	October
Average price	$380
Good round-trip deal	$346 or less
Good one-way deal	$187 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. 8% potential increase in price ($35 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($16 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 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 September 14, 2025.

Sat 10/1111:55 amORD - SJU

2 stops26h 04mSpirit Airlines

Sat 10/189:48 amSJU - ORD

Nonstop5h 08mSpirit Airlines

Deal found 9/14

$207

Fri 10/249:06 pmORD - SJU

Nonstop4h 45mSpirit Airlines

Tue 10/283:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 9/12

$208

Sat 10/411:57 amORD - SJU

2 stops20h 59mMultiple Airlines

Tue 10/76:22 amSJU - ORD

1 stop11h 51mMultiple Airlines

Deal found 9/12

$209

Sat 10/256:00 amORD - SJU

1 stop7h 12mSpirit Airlines

Mon 10/277:43 pmSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 9/12

$211

Wed 10/16:30 amORD - SJU

1 stop6h 41mSpirit Airlines

Sat 10/43:19 pmSJU - ORD

1 stop7h 39mSpirit Airlines

Deal found 9/12

$212

Fri 10/35:17 pmORD - SJU

1 stop6h 37mSpirit Airlines

Tue 10/73:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 9/14

$213

Sat 11/12:03 pmORD - SJU

Nonstop4h 39mSpirit Airlines

Thu 11/62:38 pmSJU - ORD

Nonstop5h 22mSpirit Airlines

Deal found 9/12

$215

Sat 12/67:35 amORD - SJU

1 stop11h 09mSpirit Airlines

Wed 12/172:38 pmSJU - ORD

Nonstop5h 22mSpirit Airlines

Deal found 9/12

$216

Thu 9/1812:05 pmORD - SJU

1 stop11h 49mSpirit Airlines

Sat 9/273:19 pmSJU - ORD

1 stop7h 39mSpirit Airlines

Deal found 9/13

$217

Thu 10/302:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Thu 11/138:10 amSJU - ORD

Nonstop5h 22mUnited Airlines

Deal found 9/12

$218

Tue 10/146:58 pmORD - SJU

2 stops30h 04mMultiple Airlines

Sat 10/189:48 amSJU - ORD

Nonstop5h 08mMultiple Airlines

Deal found 9/11

$219

Mon 9/225:17 pmORD - SJU

1 stop6h 37mSpirit Airlines

Wed 10/16:44 amSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 9/13

$220

Best flights from Illinois to Puerto Rico
Discover carefully curated flight deals from Illinois to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2025.

Tue 11/42:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Fri 11/78:10 amSJU - ORD

Nonstop5h 22mUnited Airlines

Deal found 9/13

$218

Fri 10/315:20 amORD - SJU

1 stop10h 13mDelta

Wed 11/57:00 amSJU - ORD

1 stop12h 22mDelta

Deal found 9/14

$227

Sat 11/11:45 pmMDW - SJU

2 stops9h 00mSouthwest

Tue 11/411:20 amSJU - MDW

1 stop9h 05mSouthwest

Deal found 9/12

$252

Sun 9/288:49 pmORD - PSE

1 stop11h 41mFrontier

Thu 10/210:15 amPSE - ORD

2 stops14h 05mFrontier

Deal found 9/13

$260

Tue 11/46:43 amEVV - SJU

2 stops15h 09mAmerican Airlines

Tue 11/116:00 amSJU - EVV

2 stops17h 18mAmerican Airlines

Deal found 9/13

$285

Fri 11/1410:18 amORD - BQN

1 stop14h 46mMultiple Airlines

Sun 11/163:59 amBQN - ORD

1 stop10h 17mMultiple Airlines

Deal found 9/13

$288

Tue 11/113:07 pmORD - SJU

1 stop7h 29mUnited Airlines

Fri 11/148:10 amSJU - ORD

Nonstop5h 22mUnited Airlines

Deal found 9/13

$223

Tue 10/217:00 amORD - SJU

1 stop8h 25mDelta

Sat 10/257:00 amSJU - ORD

1 stop11h 22mDelta

Deal found 9/13

$227

Sun 11/92:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Tue 11/182:05 amSJU - ORD

1 stop9h 43mUnited Airlines

Deal found 9/11

$223

Sat 11/81:00 pmMDW - SJU

1 stop9h 15mSouthwest

Wed 11/192:05 pmSJU - MDW

2 stops10h 30mSouthwest

Deal found 9/11

$252

Fri 10/3111:24 amORD - BQN

2 stops13h 53mFrontier

Sat 11/13:12 amBQN - ORD

1 stop11h 14mFrontier

Deal found 9/12

$262

Sat 11/16:08 amORD - SJU

1 stop7h 03mDelta

Wed 11/197:15 amSJU - ORD

1 stop12h 30mDelta

Deal found 9/12

$252

Last-minute flights from Illinois to Puerto Rico
Discover last-minute flight deals from Illinois to Puerto Rico. Data last updated September 14, 2025 and is based on user searches.

Thu 9/1812:05 pmORD - SJU

1 stop11h 49mSpirit Airlines

Sat 9/273:19 pmSJU - ORD

1 stop7h 39mSpirit Airlines

Deal found 9/13

$217

Mon 9/225:17 pmORD - SJU

1 stop6h 37mSpirit Airlines

Wed 10/16:44 amSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 9/13

$220

Wed 10/16:30 amORD - SJU

1 stop6h 41mSpirit Airlines

Sat 10/43:19 pmSJU - ORD

1 stop7h 39mSpirit Airlines

Deal found 9/12

$212

Fri 10/35:17 pmORD - SJU

1 stop6h 37mSpirit Airlines

Tue 10/73:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 9/14

$213

Sat 10/411:57 amORD - SJU

2 stops20h 59mMultiple Airlines

Tue 10/76:22 amSJU - ORD

1 stop11h 51mMultiple Airlines

Deal found 9/12

$209

Sat 10/1111:55 amORD - SJU

2 stops26h 04mSpirit Airlines

Sat 10/189:48 amSJU - ORD

Nonstop5h 08mSpirit Airlines

Deal found 9/14

$207

Tue 10/146:58 pmORD - SJU

2 stops30h 04mMultiple Airlines

Sat 10/189:48 amSJU - ORD

Nonstop5h 08mMultiple Airlines

Deal found 9/11

$219

Fri 10/179:06 pmORD - SJU

Nonstop4h 45mSpirit Airlines

Fri 10/247:43 pmSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 9/12

$215

Sat 10/186:00 amSTL - SJU

1 stop16h 05mAmerican Airlines

Wed 10/225:30 amSJU - STL

1 stop11h 33mAmerican Airlines

Deal found 9/12

$225

Fri 10/249:06 pmORD - SJU

Nonstop4h 45mSpirit Airlines

Tue 10/283:19 pmSJU - ORD

1 stop7h 14mSpirit Airlines

Deal found 9/12

$208

Sat 10/256:00 amORD - SJU

1 stop7h 12mSpirit Airlines

Mon 10/277:43 pmSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 9/12

$211

Thu 10/302:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Mon 11/34:52 pmSJU - ORD

Nonstop5h 28mUnited Airlines

Deal found 9/14

$218

One-way flights from Illinois to Puerto Rico
Search for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 14, 2025.

Mon 12/86:55 amORD - SJU

Nonstop4h 38mSpirit Airlines

Deal found 9/12

$108

Tue 10/282:20 pmORD - SJU

Nonstop4h 40mUnited Airlines

Deal found 9/12

$109

Sat 12/610:15 amORD - SJU

1 stop8h 29mSpirit Airlines

Deal found 9/12

$110

Sun 9/2112:55 pmORD - SJU

Nonstop4h 39mSpirit Airlines

Deal found 9/12

$112

Mon 11/176:40 amORD - SJU

1 stop9h 14mFrontier

Deal found 9/12

$113

Sat 10/256:00 amSTL - SJU

1 stop7h 11mDelta

Deal found 9/14

$113

Wed 11/52:25 pmMDW - SJU

2 stops8h 10mSouthwest

Deal found 9/14

$114

Wed 10/156:40 amORD - SJU

1 stop18h 22mFrontier

Deal found 9/12

$115

Tue 9/236:30 amORD - SJU

1 stop6h 41mSpirit Airlines

Deal found 9/12

$116

Sun 10/266:45 amORD - SJU

1 stop16h 14mAmerican Airlines

Deal found 9/14

$117

Fri 11/146:05 amORD - SJU

2 stops17h 20mSouthwest

Deal found 9/14

$120

Fri 10/177:51 pmORD - SJU

1 stop17h 21mSpirit Airlines

Deal found 9/12

$121

Cheapflights Fare Finder

Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 11/4

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 11/7

8:10 am-11:32 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 11/11

3:07 pm-12:36 am

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Fri 11/14

8:10 am-11:32 am

Nonstop5h 22m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 11/9

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-9:48 am

1 stop9h 43m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/31

5:20 am-4:33 pm

1 stop10h 13m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:00 am-5:22 pm

1 stop12h 22m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/1

1:45 pm-11:45 pm

2 stops9h 00m

San Juan Luis Munoz Marin Intl

Tue 11/4

11:20 am-6:25 pm

1 stop9h 05m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/8

1:00 pm-12:15 am

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Wed 11/19

2:05 pm-10:35 pm

2 stops10h 30m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 11/1

6:08 am-2:11 pm

1 stop7h 03m

San Juan Luis Munoz Marin Intl

Wed 11/19

7:15 am-5:45 pm

1 stop12h 30m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 11/11

1:36 pm-12:36 am

1 stop9h 00m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-10:45 am

1 stop10h 40m

$256

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 9/28

8:49 pm-9:30 am

1 stop11h 41m

Ponce Mercedita

Thu 10/2

10:15 am-11:20 pm

2 stops14h 05m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results

...

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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Puerto Rico

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 June is currently the most expensive (average of $339). 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?

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

The most flights from USIL to PR0 are scheduled on a Friday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Related info for your journey

How long is the flight from Illinois to Puerto Rico?
There are many flights that can get you from Illinois to Puerto Rico in 4h 40m. Fly via United Airlines, Delta, or Southwest to get the fastest option. Illinois and Puerto Rico are separated by a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
What are the cheapest airlines to fly from Illinois to Puerto Rico one-way?
For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $113 and $113 on Delta and Southwest, 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 June is currently the most expensive (average of $339). 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

Top 7 airlines flying from Illinois to Puerto Rico

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$106	Average$305	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$139	Average$335	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$194	Average$576	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$196	Average$410	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$271	Average$418	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$277	Average$509	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$364	Average$488	FlexibilityNo cancel fee	On-time63%

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$108+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Illinois to Puerto Rico with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 September 14, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Illinois to Puerto Rico

Cheapest flights from Illinois to Puerto RicoExplore 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 September 14, 2025.

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 September 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Puerto Rico

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

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 September 14, 2025.

Weekly flight availability from Illinois to Puerto Rico

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.

How long is the flight from Illinois to Puerto Rico?

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

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

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

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

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

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 Illinois to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Illinois to Puerto Rico

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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 September 14, 2025.