Which airline has the best punctuality record on Chicago to Puerto Rico flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

What is the cheapest airline that flies from Chicago O'Hare Intl to Puerto Rico?

Delta, Frontier, and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Puerto Rico

What is the most punctual flight time for Chicago to Puerto Rico flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How many flights depart from Chicago O'Hare Intl Airport to Puerto Rico on average per week?

As of May 2026, there are 54 flights per week flying from Chicago O'Hare Intl Airport to Puerto Rico. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

What airlines fly to Puerto Rico?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Puerto Rico from Chicago O'Hare Intl Airport according to our data. Spirit Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 7 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.

How often are flights from Chicago to Puerto Rico delayed?

Historically, on average around 22% of flights between Chicago and Puerto Rico have experienced a delay on any given week. The average delay length over the past 12 months has been 140 minutes.

How many flights depart from Chicago O'Hare Intl Airport to Puerto Rico on average per day?

7 flights are operational daily from Chicago O'Hare Intl Airport to Puerto Rico as of May 2026. The most popular departure time for this route is 8:00AM, with 61% of flights per day taking off at noon.

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Puerto Rico?

As of May 2026, there are 7 operators available to choose from for flights from Chicago O'Hare Intl Airport to Puerto Rico.

How old do you have to be to fly from Chicago O'Hare Intl Airport to Puerto Rico?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Puerto Rico.

What documentation or ID do you need to fly to Puerto Rico?

The travel and health documents you'll need for your trip to Puerto Rico may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Puerto Rico. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$108 Cheap Flights from Chicago O'Hare Intl Airport to Puerto Rico in 2026

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Find the cheapest flights from Chicago O'Hare Intl Airport to Puerto Rico

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:44 am - 6:44 am

ORD

SJU

5h 00mnonstop

7:14 pm - 11:27 pm

SJU

ORD

5h 13mnonstop

$226Frontier

Sat, Aug 8 - Thu, Aug 13

12:44 am - 6:44 am

ORD

SJU

5h 00mnonstop

6:11 pm - 10:26 pm

SJU

ORD

5h 15mnonstop

$229Frontier

Sat, Aug 8 - Tue, Aug 18

12:44 am - 6:44 am

ORD

SJU

5h 00mnonstop

7:00 am - 8:03 am

SJU

ORD

26h 03m

2 stops

$230Frontier

Sat, Aug 8 - Mon, Aug 17

5:14 pm - 11:07 pm

ORD

SJU

4h 53mnonstop

7:14 pm - 7:34 am

SJU

ORD

13h 20m

1 stop

$232American Airlines

Tue, Aug 11 - Tue, Aug 18

5:14 pm - 11:07 pm

ORD

SJU

4h 53mnonstop

7:14 pm - 9:00 am

SJU

ORD

14h 46m

1 stop

$235American Airlines

Thu, Aug 6 - Tue, Aug 11

8:02 am - 4:37 pm

ORD

SJU

7h 35m

1 stop

5:49 pm - 11:58 pm

SJU

ORD

7h 09m

1 stop

$236Delta

Wed, Aug 19 - Thu, Aug 27

2:35 pm - 12:33 am

ORD

BQN

8h 58m

1 stop

5:01 am - 1:39 pm

BQN

ORD

9h 38m

1 stop

$389JetBlue

Tue, Aug 11 - Tue, Aug 25

2:35 pm - 11:59 pm

ORD

PSE

8h 24m

1 stop

5:01 am - 1:39 pm

PSE

ORD

9h 38m

1 stop

$484JetBlue

Sun, Aug 30 - Wed, Sep 2

5:00 am - 4:11 pm

ORD

MAZ

10h 11m

2 stops

1:19 pm - 11:31 pm

MAZ

ORD

11h 12m

2 stops

$1,558United Airlines

Wed, Jun 17 - Thu, Jul 9

8:49 am - 5:21 pm

ORD

CPX

7h 32m

1 stop

10:48 am - 9:00 pm

CPX

ORD

11h 12m

2 stops

$1,558United Airlines

Wed, Jun 24 - Sat, Jul 25

Delta flights from Chicago O'Hare Intl Airport to Puerto Rico

Our best Delta deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets

Delta

Jul 4

ORD9:48 amChicago O'Hare Intl

9h 55m

1 stop

SJU8:43 pmSan Juan Luis Munoz Marin Intl

Jul 11

SJU12:56 pmSan Juan Luis Munoz Marin Intl

8h 37m

1 stop

ORD8:33 pmChicago O'Hare Intl

$256

Delta

Aug 17

ORD9:52 amChicago O'Hare Intl

11h 37m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU12:56 pmSan Juan Luis Munoz Marin Intl

8h 50m

1 stop

ORD8:46 pmChicago O'Hare Intl

$266

Delta

Aug 15

ORD1:48 pmChicago O'Hare Intl

7h 41m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 22

SJU6:48 amSan Juan Luis Munoz Marin Intl

11h 06m

1 stop

ORD4:54 pmChicago O'Hare Intl

$276

Frontier flights from Chicago O'Hare Intl Airport to Puerto Rico

Our best Frontier deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets

Frontier

Aug 8

ORD12:44 amChicago O'Hare Intl

5h 00m

SJU6:44 amSan Juan Luis Munoz Marin Intl

Aug 13

SJU7:14 pmSan Juan Luis Munoz Marin Intl

5h 13m

ORD11:27 pmChicago O'Hare Intl

$226

Frontier

Aug 8

ORD12:44 amChicago O'Hare Intl

5h 00m

SJU6:44 amSan Juan Luis Munoz Marin Intl

Aug 18

SJU6:11 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD10:26 pmChicago O'Hare Intl

$229

Frontier

Aug 8

ORD12:44 amChicago O'Hare Intl

5h 00m

SJU6:44 amSan Juan Luis Munoz Marin Intl

Aug 17

SJU7:00 amSan Juan Luis Munoz Marin Intl

26h 03m

2 stops

ORD8:03 amChicago O'Hare Intl

$230

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/8

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Thu 8/13

7:14 pm-11:27 pm

Nonstop5h 13m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/8

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Tue 8/18

6:11 pm-10:26 pm

Nonstop5h 15m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/8

12:44 am-6:44 am

Nonstop5h 00m

San Juan Luis Munoz Marin Intl

Mon 8/17

7:00 am-8:03 am

2 stops26h 03m

$230

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/11

5:14 pm-11:07 pm

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Tue 8/18

7:14 pm-7:34 am

1 stop13h 20m

$232

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/6

5:14 pm-11:07 pm

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Tue 8/11

7:14 pm-9:00 am

1 stop14h 46m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 8/19

8:02 am-4:37 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 8/27

5:49 pm-11:58 pm

1 stop7h 09m

$236

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 8/11

2:35 pm-12:33 am

1 stop8h 58m

Aguadilla Borinquen

Tue 8/25

5:01 am-1:39 pm

1 stop9h 38m

$389

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sun 8/30

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Wed 9/2

5:01 am-1:39 pm

1 stop9h 38m

$484

ChicagoMayagüez

ORD - MAZ

ORDMAZ

Chicago O'Hare Intl

Wed 6/17

5:00 am-4:11 pm

2 stops10h 11m

Mayagüez Eugenio M De Hostos

Thu 7/9

1:19 pm-11:31 pm

2 stops11h 12m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 6/24

8:49 am-5:21 pm

1 stop7h 32m

Culebra

Sat 7/25

10:48 am-9:00 pm

2 stops11h 12m

$1,558

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Puerto Rico

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Puerto Rico?

If you don’t want to visit Puerto Rico in September, then you should wait until August to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $115.

What is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from Chicago O'Hare Intl Airport is on a Monday. momondo users have found tickets for Monday departures for as low as $384. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Friday, with ticket prices averaging around $469.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago O'Hare Intl Airport to Puerto Rico during this time can be as low as $373. In contrast, the most expensive time of day to depart to Puerto Rico is at noon when prices are around $491.

What is the cheapest Chicago O'Hare Intl to Puerto Rico flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - Puerto Rico flight prices

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago O'Hare Intl Airport for as low as $349 on momondo.

Can stopping save me money on Chicago O'Hare Intl Airport to Puerto Rico flights?

You could potentially save up to 1% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Puerto Rico flight.

Cheap Chicago O'Hare Intl Airport to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Puerto Rico

Best Price Found	$148
Fastest flight time	4h 37m
Direct flights	Every day
Airports in Puerto Rico	20 airports

The best one-way flight to Puerto Rico from Chicago O'Hare Intl Airport in the past 72 hours is $148. The best round-trip flight deal from Chicago O'Hare Intl Airport to Puerto Rico found on momondo in the last 72 hours is $317.

The fastest flight from Chicago O'Hare Intl Airport to Puerto Rico takes 4h 37m

Direct flights go from Chicago O'Hare Intl Airport to Puerto Rico every day.

There are 20 airports in Puerto Rico. From Chicago O'Hare Intl Airport there are direct flights to San Juan Luis Munoz Marin Intl (SJU).

Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Puerto Rico

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Puerto Rico?
Prices for flights from Chicago O'Hare Intl Airport to Puerto Rico are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Puerto Rico?
As of May 2026, there are 7 operators available to choose from for flights from Chicago O'Hare Intl Airport to Puerto Rico.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Puerto Rico?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Puerto Rico.
What documentation or ID do you need to fly to Puerto Rico?
The travel and health documents you'll need for your trip to Puerto Rico may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Puerto Rico. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Puerto Rico?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Puerto Rico, the leading plane model is Airbus A321neo, making up 43.18% of the total bookings. Other popular models include Boeing 737-800 with 18.98%, Airbus A320-100/200 with 13.19%, and Airbus A318/A319/A320/A321 with 9.12%.

Best airlines flying from Chicago O'Hare Intl Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Puerto Rico with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $119	Free Cancellation	Rating 7.2 2,983 reviews	Search JetBlue flights
Frontier	PriceFrom $130	Free Cancellation	Rating 5.6 2,945 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $140	Free Cancellation	Rating 6.2 8,614 reviews	Search Spirit Airlines flights
Delta	PriceFrom $143	Free Cancellation	Rating 7.9 8,450 reviews	Search Delta flights
United Airlines	PriceFrom $256	Free Cancellation	Rating 7.4 9,731 reviews	Search United Airlines flights
American Airlines	PriceFrom $307	Free Cancellation	Rating 7.1 11,645 reviews	Search American Airlines flights
Southwest	PriceFrom $376	Free Cancellation	Rating 7.9 4,284 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Puerto Rico?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Rico from Chicago.

Can I find flights from Chicago to Puerto Rico with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Puerto Rico from Chicago with this policy.

How can momondo help me find flights from Chicago to Puerto Rico?

Once all potential Chicago to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Puerto Rico right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Puerto Rico flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Puerto Rico trip

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Flights to San Juanfrom $182

Flights to Aguadillafrom $212

Flights to Poncefrom $178

Flights to Culebrafrom $499

Flights to Mayagüezfrom $448

Cheap flights from Chicago O'Hare Intl Airport to Puerto Rico from $108

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Delta flights from Chicago O'Hare Intl Airport to Puerto Rico

Our best Delta deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets

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Our best Frontier deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets

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Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.

See travel insights to Puerto Rico from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Puerto Rico

What is the cheapest month to fly to Puerto Rico?

What is the cheapest day to depart on your flight to Puerto Rico?

What is the cheapest time of day to depart on your flight to Puerto Rico?

What is the cheapest Chicago O'Hare Intl to Puerto Rico flight route?

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Puerto Rico?

Can stopping save me money on Chicago O'Hare Intl Airport to Puerto Rico flights?

What is the cheapest airline that flies from Chicago O'Hare Intl to Puerto Rico?

What airlines fly to Puerto Rico?

How often are flights from Chicago to Puerto Rico delayed?

What is the most punctual flight time for Chicago to Puerto Rico flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Chicago to Puerto Rico flights?

How many flights depart from Chicago O'Hare Intl Airport to Puerto Rico on average per day?

How many flights depart from Chicago O'Hare Intl Airport to Puerto Rico on average per week?

Cheap Chicago O'Hare Intl Airport to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Puerto Rico

Best Price Found

Fastest flight time

Direct flights

Airports in Puerto Rico

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Puerto Rico

Best airlines flying from Chicago O'Hare Intl Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Puerto Rico with momondo

Why use momondo?

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Puerto Rico

Popular cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo

Chicago O'Hare Intl Airport flight routes

According to popular flight searches on momondo this year

Puerto Rico flight routes

According to popular flight searches on momondo this year

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List of cabin classes available on flights landing in Puerto Rico. Availability may vary depending on flight origin and airline.

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