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

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

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 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 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.

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

83 flights are operational weekly from Puerto Rico to Chicago as of January 2026. The most popular departure day for this route is Sat, with 16% of flights per week taking off on this day.

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 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 37% 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.

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 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.

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.

$96 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.

11:59 pm - 9:48 am

SJU

ORD

10h 49m

1 stop

3:15 pm - 12:07 am

ORD

SJU

7h 52m

1 stop

$119JetBlue

Fri, May 1 - Mon, May 4

1:00 pm - 9:36 pm

SJU

ORD

9h 36m

1 stop

10:35 am - 9:01 pm

ORD

SJU

9h 26m

1 stop

$120JetBlue

Thu, May 7 - Mon, May 11

3:26 am - 11:25 am

SJU

ORD

8h 59m

1 stop

6:45 am - 5:30 pm

ORD

SJU

9h 45m

1 stop

$126JetBlue

Thu, Mar 19 - Sun, Mar 22

12:30 pm - 7:26 pm

SJU

ORD

7h 56m

1 stop

3:15 pm - 12:59 am

ORD

SJU

8h 44m

1 stop

$127JetBlue

Fri, Jun 5 - Mon, Jun 8

12:32 pm - 3:48 pm

SJU

ORD

5h 16mnonstop

12:59 pm - 12:29 am

ORD

SJU

9h 30m

1 stop

$153Multiple Airlines

Thu, Feb 26 - Sat, Feb 28

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

11:07 am - 2:26 pm

SJU

MDW

29h 19m

1 stop

9:22 pm - 9:54 am

MDW

SJU

10h 32m

1 stop

$194Frontier

Wed, Feb 18 - Mon, Feb 23

2:38 am - 9:15 am

BQN

ORD

7h 37m

1 stop

6:00 am - 1:32 am

ORD

BQN

18h 32m

2 stops

$307Multiple Airlines

Wed, Apr 29 - Sun, May 3

11:44 am - 10:44 am

VQS

ORD

24h 00m

2 stops

2:38 pm - 3:53 pm

ORD

VQS

24h 15m

1 stop

$991United Airlines

Wed, Apr 8 - Sat, Apr 11

1:19 pm - 8:20 pm

MAZ

ORD

9h 01m

1 stop

1:02 pm - 4:11 pm

ORD

MAZ

25h 09m

2 stops

$2,022United Airlines

Thu, Feb 19 - Sat, Feb 21

Frontier flights from Puerto Rico to Chicago

Our best Frontier deals on Puerto Rico to Chicago flight tickets

Frontier

Feb 18

SJU5:25 pmSan Juan Luis Munoz Marin Intl

19h 21m

1 stop

ORD10:46 amChicago O'Hare Intl

Mar 2

ORD2:13 pmChicago O'Hare Intl

10h 12m

1 stop

SJU2:25 amSan Juan Luis Munoz Marin Intl

$161

Frontier

Feb 19

SJU7:54 pmSan Juan Luis Munoz Marin Intl

21h 24m

1 stop

ORD3:18 pmChicago O'Hare Intl

Feb 23

ORD2:13 pmChicago O'Hare Intl

10h 12m

1 stop

SJU2:25 amSan Juan Luis Munoz Marin Intl

$165

Frontier

Feb 18

SJU11:07 amSan Juan Luis Munoz Marin Intl

25h 39m

1 stop

ORD10:46 amChicago O'Hare Intl

Feb 23

ORD5:05 amChicago O'Hare Intl

7h 57m

1 stop

SJU3:02 pmSan Juan Luis Munoz Marin Intl

$182

Spirit Airlines flights from Puerto Rico to Chicago

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

Spirit Airlines

Jan 30

SJU1:22 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD4:37 pmChicago O'Hare Intl

Feb 3

ORD12:17 pmChicago O'Hare Intl

4h 32m

SJU6:49 pmSan Juan Luis Munoz Marin Intl

$169

Spirit Airlines

Jan 31

SJU1:22 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD4:37 pmChicago O'Hare Intl

Feb 3

ORD12:17 pmChicago O'Hare Intl

4h 32m

SJU6:49 pmSan Juan Luis Munoz Marin Intl

$171

Spirit Airlines

Jan 30

SJU1:22 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD4:37 pmChicago O'Hare Intl

Feb 1

ORD12:17 pmChicago O'Hare Intl

4h 32m

SJU6:49 pmSan Juan Luis Munoz Marin Intl

$176

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/1

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Mon 5/4

3:15 pm-12:07 am

1 stop7h 52m

$119

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/7

1:00 pm-9:36 pm

1 stop9h 36m

Chicago O'Hare Intl

Mon 5/11

10:35 am-9:01 pm

1 stop9h 26m

$120

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/19

3:26 am-11:25 am

1 stop8h 59m

Chicago O'Hare Intl

Sun 3/22

6:45 am-5:30 pm

1 stop9h 45m

$126

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 6/5

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Mon 6/8

3:15 pm-12:59 am

1 stop8h 44m

$127

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sat 2/28

12:59 pm-12:29 am

1 stop9h 30m

$153

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

Wed 2/18

11:07 am-2:26 pm

1 stop29h 19m

Chicago Midway

Mon 2/23

9:22 pm-9:54 am

1 stop10h 32m

$194

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 4/29

2:38 am-9:15 am

1 stop7h 37m

Chicago O'Hare Intl

Sun 5/3

6:00 am-1:32 am

2 stops18h 32m

$307

ViequesChicago

VQS - ORD

VQSORD

Vieques

Wed 4/8

11:44 am-10:44 am

2 stops24h 00m

Chicago O'Hare Intl

Sat 4/11

2:38 pm-3:53 pm

1 stop24h 15m

$991

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

Thu 2/19

1:19 pm-8:20 pm

1 stop9h 01m

Chicago O'Hare Intl

Sat 2/21

1:02 pm-4:11 pm

2 stops25h 09m

$2,022

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 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 February is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $222. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $266.

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 $378. 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 $257. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $481.

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 $330 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 $284 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.

Can stopping save me money on Puerto Rico to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Puerto Rico to Chicago flight.

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	$205
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 $205. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $261.

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 41.32% of the total bookings. Other popular models include Airbus A318/A319/A320/A321 with 13.48%, Airbus A320 (sharklets) with 13.33%, and Airbus A320-100/200 with 9.30%.

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 8,111 reviews	Search Delta flights
Spirit Airlines	PriceFrom $118	Free Cancellation	Rating 6.3 8,375 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $120	Free Cancellation	Rating 7.2 2,896 reviews	Search JetBlue flights
Frontier	PriceFrom $137	Free Cancellation	Rating 5.7 3,059 reviews	Search Frontier flights
United Airlines	PriceFrom $256	Free Cancellation	Rating 7.4 9,198 reviews	Search United Airlines flights
American Airlines	PriceFrom $257	Free Cancellation	Rating 7.2 11,197 reviews	Search American Airlines flights
Southwest	PriceFrom $419	Free Cancellation	Rating 8.0 4,269 reviews	Search Southwest flights

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Hammond

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Saint Joseph

Portage

Lansing

Schererville

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 $96

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 4/13. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Puerto Rico to Chicago

Recent round-trip flight deals from Puerto Rico to Chicago

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Frontier flights from Puerto Rico to Chicago

Our best Frontier deals on Puerto Rico to Chicago flight tickets

Spirit Airlines flights from Puerto Rico to Chicago

Our best Spirit 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 February is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $222. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $266.

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 $257. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $481.

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.

Can stopping save me money on Puerto Rico to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Puerto Rico to Chicago flight.

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

Spirit Airlines, Frontier, and United 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?

83 flights are operational weekly from Puerto Rico to Chicago as of January 2026. The most popular departure day for this route is Sat, with 16% 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