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.

How often are flights from Chicago to Puerto Rico delayed?

Historically, on average around 18% 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 143 minutes.

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 44% 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.

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

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

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

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

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

12 flights are operational daily from Chicago O'Hare Intl Airport to Puerto Rico as of March 2026. The most popular departure time for this route is 8:00AM, with 40% of flights per day taking off at noon.

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 March 2026, there are 86 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.

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

As of March 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.

$88 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.

5:30 pm - 2:02 am

ORD

BQN

7h 32m

1 stop

4:28 pm - 11:13 pm

BQN

ORD

7h 45m

1 stop

$196Frontier

Fri, May 15 - Sat, May 23

2:20 pm - 12:29 am

ORD

SJU

9h 09m

1 stop

3:37 pm - 11:06 pm

SJU

ORD

8h 29m

1 stop

$211Frontier

Thu, Apr 16 - Mon, Apr 20

12:40 pm - 4:49 am

ORD

SJU

15h 09m

1 stop

6:00 am - 12:37 pm

SJU

ORD

7h 37m

1 stop

$212Frontier

Tue, May 26 - Fri, May 29

8:00 am - 2:01 am

ORD

SJU

17h 01m

1 stop

6:41 pm - 9:37 am

SJU

ORD

15h 56m

1 stop

$213Frontier

Sat, May 2 - Sat, May 16

12:45 pm - 9:59 pm

ORD

SJU

8h 14m

1 stop

12:57 pm - 8:05 am

SJU

ORD

20h 08m

2 stops

$214Spirit Airlines

Sat, Apr 11 - Thu, Apr 16

7:50 am - 12:58 am

ORD

SJU

16h 08m

1 stop

4:34 pm - 8:49 pm

SJU

ORD

5h 15mnonstop

$215Spirit Airlines

Thu, Apr 16 - Thu, Apr 30

4:34 pm - 12:52 am

ORD

SJU

7h 18m

1 stop

3:23 pm - 10:39 pm

SJU

ORD

8h 16m

1 stop

$216Frontier

Tue, Apr 7 - Fri, May 1

5:05 am - 6:55 pm

ORD

SJU

12h 50m

1 stop

3:37 pm - 11:06 pm

SJU

ORD

8h 29m

1 stop

$217Multiple Airlines

Sun, Apr 12 - Mon, May 4

8:00 am - 1:42 pm

ORD

SJU

4h 42mnonstop

2:37 pm - 6:50 pm

SJU

ORD

5h 13mnonstop

$218Spirit Airlines

Mon, May 4 - Sat, May 9

10:00 am - 3:39 pm

ORD

SJU

4h 39mnonstop

6:09 pm - 11:13 pm

SJU

ORD

30h 04m

1 stop

$219Multiple Airlines

Sun, May 3 - Mon, May 11

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

May 15

ORD5:30 pmChicago O'Hare Intl

7h 32m

1 stop

BQN2:02 amAguadilla Borinquen

May 23

BQN4:28 pmAguadilla Borinquen

7h 45m

1 stop

ORD11:13 pmChicago O'Hare Intl

$196

Frontier

Apr 16

ORD2:20 pmChicago O'Hare Intl

9h 09m

1 stop

SJU12:29 amSan Juan Luis Munoz Marin Intl

Apr 20

SJU3:37 pmSan Juan Luis Munoz Marin Intl

8h 29m

1 stop

ORD11:06 pmChicago O'Hare Intl

$211

Frontier

May 26

ORD12:40 pmChicago O'Hare Intl

15h 09m

1 stop

SJU4:49 amSan Juan Luis Munoz Marin Intl

May 29

SJU6:00 amSan Juan Luis Munoz Marin Intl

7h 37m

1 stop

ORD12:37 pmChicago O'Hare Intl

$212

Spirit Airlines flights from Chicago O'Hare Intl Airport to Puerto Rico

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

Spirit Airlines

Apr 3

ORD8:56 pmChicago O'Hare Intl

4h 33m

SJU2:29 amSan Juan Luis Munoz Marin Intl

Apr 10

SJU1:29 amSan Juan Luis Munoz Marin Intl

5h 16m

ORD5:45 amChicago O'Hare Intl

$212

Spirit Airlines

Apr 6

ORD8:56 pmChicago O'Hare Intl

4h 33m

SJU2:29 amSan Juan Luis Munoz Marin Intl

Apr 14

SJU7:54 pmSan Juan Luis Munoz Marin Intl

14h 42m

1 stop

ORD9:36 amChicago O'Hare Intl

$214

Spirit Airlines

Apr 16

ORD7:50 amChicago O'Hare Intl

16h 08m

1 stop

SJU12:58 amSan Juan Luis Munoz Marin Intl

Apr 30

SJU4:34 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD8:49 pmChicago O'Hare Intl

$215

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

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Fri 5/15

5:30 pm-2:02 am

1 stop7h 32m

Aguadilla Borinquen

Sat 5/23

4:28 pm-11:13 pm

1 stop7h 45m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/16

2:20 pm-12:29 am

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Mon 4/20

3:37 pm-11:06 pm

1 stop8h 29m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/26

12:40 pm-4:49 am

1 stop15h 09m

San Juan Luis Munoz Marin Intl

Fri 5/29

6:00 am-12:37 pm

1 stop7h 37m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/2

8:00 am-2:01 am

1 stop17h 01m

San Juan Luis Munoz Marin Intl

Sat 5/16

6:41 pm-9:37 am

1 stop15h 56m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/11

12:45 pm-9:59 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Thu 4/16

12:57 pm-8:05 am

2 stops20h 08m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/16

7:50 am-12:58 am

1 stop16h 08m

San Juan Luis Munoz Marin Intl

Thu 4/30

4:34 pm-8:49 pm

Nonstop5h 15m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/7

4:34 pm-12:52 am

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:39 pm

1 stop8h 16m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 4/12

5:05 am-6:55 pm

1 stop12h 50m

San Juan Luis Munoz Marin Intl

Mon 5/4

3:37 pm-11:06 pm

1 stop8h 29m

$217

Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/4

8:00 am-1:42 pm

Nonstop4h 42m

San Juan Luis Munoz Marin Intl

Sat 5/9

2:37 pm-6:50 pm

Nonstop5h 13m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/3

10:00 am-3:39 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 5/11

6:09 pm-11:13 pm

1 stop30h 04m

$219

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 May to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $352.

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 $383. 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 $458.

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 $372. In contrast, the most expensive time of day to depart to Puerto Rico is at noon when prices are around $486.

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 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 $385 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 $335 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Puerto Rico flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Puerto Rico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Puerto Rico.

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	$182
Fastest flight time	4h 31m
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 $182. The best round-trip flight deal from Chicago O'Hare Intl Airport to Puerto Rico found on momondo in the last 72 hours is $324.

The fastest flight from Chicago O'Hare Intl Airport to Puerto Rico takes 4h 31m

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

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 March 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 40.57% of the total bookings. Other popular models include Boeing 737-800 with 20.84%, Airbus A318/A319/A320/A321 with 19.45%, and Airbus A320 (sharklets) with 6.39%.

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
Frontier	PriceFrom $114	Free Cancellation	Rating 5.7 3,013 reviews	Search Frontier flights
JetBlue	PriceFrom $119	Free Cancellation	Rating 7.2 2,909 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $139	Free Cancellation	Rating 6.3 8,552 reviews	Search Spirit Airlines flights
Delta	PriceFrom $143	Free Cancellation	Rating 7.9 8,357 reviews	Search Delta flights
United Airlines	PriceFrom $254	Free Cancellation	Rating 7.4 9,501 reviews	Search United Airlines flights
American Airlines	PriceFrom $312	Free Cancellation	Rating 7.1 11,520 reviews	Search American Airlines flights
Southwest	PriceFrom $377	Free Cancellation	Rating 8.0 4,333 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 $55

Flights to Aguadillafrom $191

Flights to Poncefrom $176

Flights to Mayagüezfrom $339

Flights to Culebrafrom $377

Cheap flights from Chicago O'Hare Intl Airport to Puerto Rico from $88

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

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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 to Puerto Rico?

What cabin class options are available on Chicago O'Hare Intl to Puerto Rico flights?

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

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

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Chicago O'Hare Intl Airport 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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