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 5% of their flights experiencing any sort of delay.

What airlines fly to Chicago?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago 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. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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.

How many flights depart from Puerto Rico to Chicago on average per day?

The number of flights available between Puerto Rico and Chicago is 11 per day as of January 2026. The most frequent departure time is 4:00PM, with 50% of daily flights leaving at noon.

How many flights depart from Puerto Rico to Chicago on average per week?

82 flights are operational weekly from Puerto Rico to Chicago as of January 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Puerto Rico to Chicago depends on which airport you fly into and out of. Flying from San Juan to Chicago O'Hare Intl Airport is 5h 15m on average, while flying from Aguadilla to Chicago O'Hare Intl Airport is 7h 53m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What is the cheapest airline that flies from Puerto Rico to Chicago?

Frontier, JetBlue, and Spirit Airlines are the most popular carriers operating from Puerto Rico to Chicago

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 171 minutes.

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.

When did momondo last update prices for flights from Puerto Rico to Chicago?

Prices for flights from Puerto Rico to Chicago were last updated today.

How many operators does momondo search for flights from Puerto Rico to Chicago?

As of January 2026, there are 7 operators available to choose from for flights from Puerto Rico to Chicago.

How old do you have to be to fly from Puerto Rico to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Puerto Rico to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago 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.

$91 Cheap Flights from Puerto Rico to Chicago in 2026

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Find the cheapest flights from Puerto Rico to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Puerto Rico to Chicago

Enter your travel dates to find the best prices.

11:52 am - 6:18 pm

SJU

ORD

8h 26m

1 stop

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

$150Spirit Airlines

Thu, Feb 26 - Sat, Feb 28

3:17 pm - 10:59 pm

SJU

ORD

9h 42m

1 stop

12:41 pm - 11:44 pm

ORD

SJU

9h 03m

1 stop

$151JetBlue

Mon, Mar 2 - Fri, Mar 6

4:40 pm - 11:47 pm

SJU

ORD

9h 07m

1 stop

8:16 pm - 3:31 pm

ORD

SJU

17h 15m

1 stop

$152Spirit Airlines

Wed, Feb 11 - Wed, Mar 4

5:10 am - 11:54 am

SJU

ORD

8h 44m

1 stop

12:59 pm - 12:29 am

ORD

SJU

9h 30m

1 stop

$153JetBlue

Thu, Feb 26 - Sat, Feb 28

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

7:45 am - 6:05 pm

ORD

SJU

8h 20m

1 stop

$165Multiple Airlines

Thu, Feb 5 - Sun, Feb 8

6:00 am - 1:56 pm

SJU

MDW

9h 56m

1 stop

9:22 pm - 9:54 am

MDW

SJU

10h 32m

1 stop

$182Frontier

Thu, Feb 26 - Mon, Mar 2

8:00 am - 7:52 pm

SJU

MDW

13h 52m

1 stop

7:00 pm - 12:43 am

MDW

SJU

27h 43m

1 stop

$183Frontier

Thu, Feb 5 - Mon, Feb 9

12:56 pm - 4:40 pm

BQN

ORD

29h 44m

1 stop

7:45 am - 10:28 pm

ORD

BQN

12h 43m

2 stops

$347Multiple Airlines

Fri, Jan 30 - Tue, Feb 3

12:15 am - 9:13 am

BQN

ORD

9h 58m

1 stop

2:30 pm - 11:09 pm

ORD

BQN

7h 39m

1 stop

$416United Airlines

Mon, Apr 13 - Tue, Apr 21

1:09 am - 2:40 pm

BQN

ORD

15h 31m

2 stops

12:45 pm - 11:57 pm

ORD

BQN

9h 12m

1 stop

$496United Airlines

Wed, Feb 25 - Mon, Mar 2

JetBlue flights from Puerto Rico to Chicago

Our best JetBlue deals on Puerto Rico to Chicago flight tickets

JetBlue

Mar 2

SJU3:17 pmSan Juan Luis Munoz Marin Intl

9h 42m

1 stop

ORD10:59 pmChicago O'Hare Intl

Mar 6

ORD12:41 pmChicago O'Hare Intl

9h 03m

1 stop

SJU11:44 pmSan Juan Luis Munoz Marin Intl

$151

JetBlue

Feb 26

SJU5:10 amSan Juan Luis Munoz Marin Intl

8h 44m

1 stop

ORD11:54 amChicago O'Hare Intl

Feb 28

ORD12:59 pmChicago O'Hare Intl

9h 30m

1 stop

SJU12:29 amSan Juan Luis Munoz Marin Intl

$153

JetBlue

Feb 5

SJU11:06 amSan Juan Luis Munoz Marin Intl

10h 25m

1 stop

ORD7:31 pmChicago O'Hare Intl

Feb 8

ORD9:15 amChicago O'Hare Intl

8h 08m

1 stop

SJU7:23 pmSan Juan Luis Munoz Marin Intl

$156

United Airlines flights from Puerto Rico to Chicago

Our best United Airlines deals on Puerto Rico to Chicago flight tickets

United Airlines

Apr 13

BQN12:15 amAguadilla Borinquen

9h 58m

1 stop

ORD9:13 amChicago O'Hare Intl

Apr 21

ORD2:30 pmChicago O'Hare Intl

7h 39m

1 stop

BQN11:09 pmAguadilla Borinquen

$416

United Airlines

Jan 28

BQN1:09 amAguadilla Borinquen

15h 40m

2 stops

ORD2:49 pmChicago O'Hare Intl

Feb 2

ORD7:30 amChicago O'Hare Intl

14h 27m

2 stops

BQN11:57 pmAguadilla Borinquen

$501

United Airlines

Jan 28

BQN1:09 amAguadilla Borinquen

8h 45m

1 stop

ORD7:54 amChicago O'Hare Intl

Feb 2

ORD2:27 pmChicago O'Hare Intl

7h 30m

1 stop

BQN11:57 pmAguadilla Borinquen

$506

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Sat 2/28

12:17 pm-6:49 pm

Nonstop4h 32m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 3/2

3:17 pm-10:59 pm

1 stop9h 42m

Chicago O'Hare Intl

Fri 3/6

12:41 pm-11:44 pm

1 stop9h 03m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/11

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

Wed 3/4

8:16 pm-3:31 pm

1 stop17h 15m

$152

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

5:10 am-11:54 am

1 stop8h 44m

Chicago O'Hare Intl

Sat 2/28

12:59 pm-12:29 am

1 stop9h 30m

$153

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/5

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:05 pm

1 stop8h 20m

$165

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/5

8:00 am-7:52 pm

1 stop13h 52m

Chicago Midway

Mon 2/9

7:00 pm-12:43 am

1 stop27h 43m

$183

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 1/30

12:56 pm-4:40 pm

1 stop29h 44m

Chicago O'Hare Intl

Tue 2/3

7:45 am-10:28 pm

2 stops12h 43m

$347

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 4/13

12:15 am-9:13 am

1 stop9h 58m

Chicago O'Hare Intl

Tue 4/21

2:30 pm-11:09 pm

1 stop7h 39m

$416

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 2/25

1:09 am-2:40 pm

2 stops15h 31m

Chicago O'Hare Intl

Mon 3/2

12:45 pm-11:57 pm

1 stop9h 12m

$496

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Puerto Rico to Chicago

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 Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $266. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Puerto Rico to Chicago during September average around $273.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $379. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Puerto Rico to Chicago for around $544.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Puerto Rico to Chicago during this time can be as low as $255. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $482.

What is the cheapest Puerto Rico to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $332 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Puerto Rico for as low as $287 on momondo.

What cabin class options are available on Puerto Rico to Chicago flights?

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

Cheap Puerto Rico to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago

Best Price Found	$195
Fastest flight time	4h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Puerto Rico in the past 72 hours is $195. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $257.

The fastest flight from Puerto Rico to Chicago takes 4h 50m

Direct flights go from Puerto Rico to Chicago every day.

There are 3 airports in Chicago. From Puerto Rico there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Puerto Rico to Chicago?
Prices for flights from Puerto Rico to Chicago were last updated today.
How many operators does momondo search for flights from Puerto Rico to Chicago?
As of January 2026, there are 7 operators available to choose from for flights from Puerto Rico to Chicago.
How old do you have to be to fly from Puerto Rico to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Puerto Rico to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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.
What is the most popular plane model from Puerto Rico to Chicago?
Based on momondo bookings for flights between Puerto Rico and Chicago, the leading plane model is Airbus A321neo, making up 43.26% of the total bookings. Other popular models include Airbus A320 (sharklets) with 12.83%, Airbus A318/A319/A320/A321 with 11.39%, and Airbus A320-100/200 with 10.17%.

Best airlines flying from Puerto Rico to Chicago

Compare and see reviews for airlines that fly from Puerto Rico to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $116	Free Cancellation	Rating 7.9 8,057 reviews	Search Delta flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,321 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $120	Free Cancellation	Rating 7.2 2,889 reviews	Search JetBlue flights
Frontier	PriceFrom $137	Free Cancellation	Rating 5.7 3,057 reviews	Search Frontier flights
United Airlines	PriceFrom $256	Free Cancellation	Rating 7.4 9,165 reviews	Search United Airlines flights
American Airlines	PriceFrom $257	Free Cancellation	Rating 7.2 11,144 reviews	Search American Airlines flights
Southwest	PriceFrom $419	Free Cancellation	Rating 8.0 4,260 reviews	Search Southwest flights

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Saint Joseph

Portage

Lansing

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Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Puerto Rico to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Puerto Rico to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Puerto Rico to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Puerto Rico are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Puerto Rico to Chicago from $91

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Puerto Rico to Chicago departing on 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Find the cheapest flights from Puerto Rico to Chicago

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JetBlue flights from Puerto Rico to Chicago

Our best JetBlue deals on Puerto Rico to Chicago flight tickets

United Airlines flights from Puerto Rico to Chicago

Our best United Airlines deals on Puerto Rico to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Puerto Rico to Chicago

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $266. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Puerto Rico to Chicago during September average around $273.

What is the cheapest day to depart on your flight to Chicago?

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Puerto Rico to Chicago during this time can be as low as $255. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $482.

What is the cheapest Puerto Rico to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

What cabin class options are available on Puerto Rico to Chicago flights?

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

What is the cheapest airline that flies from Puerto Rico to Chicago?

Frontier, JetBlue, and Spirit Airlines are the most popular carriers operating from Puerto Rico to Chicago

What airlines fly to Chicago?

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 171 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. Sunday 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 5% of their flights experiencing any sort of delay.

How many flights depart from Puerto Rico to Chicago on average per day?

The number of flights available between Puerto Rico and Chicago is 11 per day as of January 2026. The most frequent departure time is 4:00PM, with 50% of daily flights leaving at noon.

How many flights depart from Puerto Rico to Chicago on average per week?

82 flights are operational weekly from Puerto Rico to Chicago as of January 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Puerto Rico to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Puerto Rico to Chicago?

How many operators does momondo search for flights from Puerto Rico to Chicago?

How old do you have to be to fly from Puerto Rico to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Puerto Rico to Chicago?

Best airlines flying from Puerto Rico to Chicago

Compare and see reviews for airlines that fly from Puerto Rico to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago