Question 1

What airlines fly to Chicago O'Hare Intl Airport?

Accepted Answer

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Puerto Rico according to our data. Spirit Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Question 2

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

Accepted Answer

12 flights are operational daily from Puerto Rico to Chicago O'Hare Intl Airport as of December 2025. The most popular departure time for this route is 6:00AM, with 53% of flights per day taking off at noon.

Question 3

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

Accepted Answer

You could potentially save up to 11% on your flight if you consider stops on a Puerto Rico to Chicago O'Hare Intl Airport flight.

Question 4

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

Accepted Answer

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

Question 5

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

Accepted Answer

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.

Question 6

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

Accepted Answer

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $296.

Question 7

How long does it take to fly to Chicago O'Hare Intl Airport?

Accepted Answer

On average, it takes 5h 13m to fly from Puerto Rico to Chicago O'Hare Intl Airport if you fly out of San Juan (the most popular airport in Puerto Rico) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago O'Hare Intl Airport). If you’re flying out of Aguadilla and into Chicago O'Hare Intl Airport, then the flight time is around 9h 15m.

Question 8

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

Accepted Answer

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $335 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Puerto Rico for as low as $285 on momondo.

Question 9

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

Accepted Answer

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

Question 10

How often are flights from Puerto Rico to Chicago delayed?

Accepted Answer

Historically, on average around 9% of flights between Puerto Rico and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 169 minutes.

Question 11

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Accepted Answer

Flying to Chicago O'Hare Intl Airport from Puerto Rico in the evening is the least expensive time of day to depart. momondo users have found prices as low as $257 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $477. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 12

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

Accepted Answer

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $384. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Puerto Rico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $548.

Question 13

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

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

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

Accepted Answer

As of December 2025, 84 flights take off from Puerto Rico and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

Question 16

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

Accepted Answer

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

Question 17

When did momondo last update prices for flights from Puerto Rico to Chicago O'Hare Intl Airport?

Accepted Answer

Prices for flights from Puerto Rico to Chicago O'Hare Intl Airport were last updated today.

Question 18

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

Accepted Answer

The number of operators available for flights from Puerto Rico to Chicago O'Hare Intl Airport is 6 as of December 2025.

Question 19

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

Accepted Answer

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Puerto Rico to Chicago O'Hare Intl Airport.

Question 20

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

Accepted Answer

The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best Price Found	$169
Fastest flight time	5h 13m
Direct flights	Every day

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $120	Free Cancellation	Rating 7.2 2,902 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $137	Free Cancellation	Rating 6.3 8,211 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $138	Free Cancellation	Rating 5.8 3,070 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.9 8,021 reviews	Search Delta flights
American Airlines	PriceFrom $254	Free Cancellation	Rating 7.2 11,069 reviews	Search American Airlines flights
United Airlines	PriceFrom $277	Free Cancellation	Rating 7.4 9,116 reviews	Search United Airlines flights

Cheap flights from Puerto Rico to Chicago from $95

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

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $296.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

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

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

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

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

There are 4 cabin classes available to choose from on Puerto Rico to Chicago O'Hare Intl 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 Puerto Rico to Chicago O'Hare Intl Airport flights?

You could potentially save up to 11% on your flight if you consider stops on a Puerto Rico to Chicago O'Hare Intl Airport flight.

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

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

What airlines fly to Chicago O'Hare Intl Airport?

How often are flights from Puerto Rico to Chicago delayed?

Historically, on average around 9% of flights between Puerto Rico and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 169 minutes.

What is the most punctual flight time for Puerto Rico to Chicago 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. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

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

12 flights are operational daily from Puerto Rico to Chicago O'Hare Intl Airport as of December 2025. The most popular departure time for this route is 6:00AM, with 53% of flights per day taking off at noon.

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

As of December 2025, 84 flights take off from Puerto Rico and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

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When did momondo last update prices for flights from Puerto Rico to Chicago O'Hare Intl Airport?

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

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

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Puerto Rico to Chicago O'Hare Intl Airport?

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

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