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

25 flights are operational weekly from Puerto Rico to Chicago as of September 2025. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

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 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Puerto Rico and Chicago is 3 per day as of September 2025. The most frequent departure time is 3:00PM, with 84% of daily flights leaving in the afternoon.

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

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

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 07m on average, while flying from Aguadilla to Chicago O'Hare Intl Airport is 7h 03m 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 September 2025, there are 6 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.

$117 Cheap Flights from Puerto Rico to Chicago in 2025/26

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One-way

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Direct

Recent round-trip flight deals from Puerto Rico to Chicago

7:43 pm - 11:57 pmSJU-ORD

5h 14mnonstop

3:00 pm - 8:40 pmORD-SJU

4h 40mnonstop

$178Spirit Airlines

Find Deal

Fri, Oct 24 - Sat, Oct 25

11:59 am - 5:39 pmSJU-ORD

6h 40m1 stop

9:06 pm - 2:51 amORD-SJU

4h 45mnonstop

$186Spirit Airlines

Find Deal

Thu, Oct 2 - Mon, Oct 6

7:43 pm - 11:57 pmSJU-ORD

5h 14mnonstop

9:06 pm - 2:51 amORD-SJU

4h 45mnonstop

$187Spirit Airlines

Find Deal

Fri, Oct 24 - Fri, Oct 31

5:51 pm - 11:30 amSJU-ORD

18h 39m2 stops

5:40 am - 4:54 pmORD-SJU

9h 14m1 stop

$209Frontier

Find Deal

Fri, Oct 31 - Sun, Nov 2

3:56 pm - 8:03 pmSJU-ORD

5h 07mnonstop

2:20 pm - 8:00 pmORD-SJU

4h 40mnonstop

$218United Airlines

Find Deal

Thu, Oct 23 - Thu, Oct 30

1:05 am - 8:38 amSJU-ORD

8h 33m1 stop

2:20 pm - 8:00 pmORD-SJU

4h 40mnonstop

$223United Airlines

Find Deal

Wed, Oct 22 - Thu, Oct 30

1:59 am - 11:39 pmSJU-ORD

22h 40m2 stops

6:40 am - 5:54 pmORD-SJU

10h 14m1 stop

$225Frontier

Find Deal

Wed, Oct 22 - Wed, Oct 29

5:50 am - 1:20 pmSJU-MDW

8h 30m2 stops

6:55 am - 3:50 pmMDW-SJU

7h 55m1 stop

$227Southwest

Find Deal

Thu, Oct 23 - Sun, Oct 26

4:43 pm - 10:55 pmSJU-ORD

8h 12m1 stop

8:15 am - 2:53 pmORD-SJU

4h 38mnonstop

$228American Airlines

Find Deal

Thu, Nov 13 - Mon, Nov 17

5:45 am - 12:45 pmSJU-MDW

9h 00m2 stops

1:25 pm - 12:35 amMDW-SJU

9h 10m2 stops

$311Southwest

Find Deal

Tue, Nov 4 - Sun, Nov 9

Spirit Airlines flights from Puerto Rico to Chicago

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

Spirit Airlines

Oct 24

SJU7:43 pmSan Juan Luis Munoz Marin Intl

5h 14m

ORD11:57 pmChicago O'Hare Intl

Oct 25

ORD3:00 pmChicago O'Hare Intl

4h 40m

SJU8:40 pmSan Juan Luis Munoz Marin Intl

$178

Find similar

Spirit Airlines

Oct 2

SJU11:59 amSan Juan Luis Munoz Marin Intl

6h 40m

1 stop

ORD5:39 pmChicago O'Hare Intl

Oct 6

ORD9:06 pmChicago O'Hare Intl

4h 45m

SJU2:51 amSan Juan Luis Munoz Marin Intl

$186

Find similar

Spirit Airlines

Oct 24

SJU7:43 pmSan Juan Luis Munoz Marin Intl

5h 14m

ORD11:57 pmChicago O'Hare Intl

Oct 31

ORD9:06 pmChicago O'Hare Intl

4h 45m

SJU2:51 amSan Juan Luis Munoz Marin Intl

$187

Find similar

United Airlines flights from Puerto Rico to Chicago

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

United Airlines

Oct 23

SJU3:56 pmSan Juan Luis Munoz Marin Intl

5h 07m

ORD8:03 pmChicago O'Hare Intl

Oct 30

ORD2:20 pmChicago O'Hare Intl

4h 40m

SJU8:00 pmSan Juan Luis Munoz Marin Intl

$218

Find similar

United Airlines

Oct 22

SJU1:05 amSan Juan Luis Munoz Marin Intl

8h 33m

1 stop

ORD8:38 amChicago O'Hare Intl

Oct 30

ORD2:20 pmChicago O'Hare Intl

4h 40m

SJU8:00 pmSan Juan Luis Munoz Marin Intl

$223

Find similar

United Airlines

Nov 21

BQN1:09 amAguadilla Borinquen

9h 56m

1 stop

ORD9:05 amChicago O'Hare Intl

Nov 26

ORD12:00 pmChicago O'Hare Intl

9h 57m

1 stop

BQN11:57 pmAguadilla Borinquen

$478

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

Sat 10/25

3:00 pm-8:40 pm

Nonstop4h 40m

$178

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/2

11:59 am-5:39 pm

1 stop6h 40m

Chicago O'Hare Intl

Mon 10/6

9:06 pm-2:51 am

Nonstop4h 45m

$186

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

Fri 10/31

9:06 pm-2:51 am

Nonstop4h 45m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/31

5:51 pm-11:30 am

2 stops18h 39m

Chicago O'Hare Intl

Sun 11/2

5:40 am-4:54 pm

1 stop9h 14m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:59 am-11:39 pm

2 stops22h 40m

Chicago O'Hare Intl

Wed 10/29

6:40 am-5:54 pm

1 stop10h 14m

$225

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

Sun 10/26

6:55 am-3:50 pm

1 stop7h 55m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 11/13

4:43 pm-10:55 pm

1 stop8h 12m

Chicago O'Hare Intl

Mon 11/17

8:15 am-2:53 pm

Nonstop4h 38m

$228

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/4

5:45 am-12:45 pm

2 stops9h 00m

Chicago Midway

Sun 11/9

1:25 pm-12:35 am

2 stops9h 10m

$311

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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

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $225. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $270.

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 $364. 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 $519.

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 $253. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $480.

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 $327 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 $268 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 5% 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	$174
Fastest flight time	5h 07m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Puerto Rico in the past 72 hours is $174. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $339.

The fastest flight from Puerto Rico to Chicago takes 5h 07m

Direct flights go from Puerto Rico to Chicago every day.

There are 2 airports near Chicago: 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 September 2025, there are 6 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 38.16% of the total bookings. Other popular models include Boeing 737 MAX 9 with 17.60%, Airbus A320neo with 15.36%, and Airbus A321-100/200 with 14.39%.

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
Spirit Airlines	PriceFrom $136	Free Cancellation	Rating 6.3 8,019 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $137	Free Cancellation	Rating 5.8 3,174 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
United Airlines	PriceFrom $255	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
Southwest	PriceFrom $257	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
American Airlines	PriceFrom $333	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

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Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

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.

An easier way to manage your Chicago trip

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Cheap flights from Puerto Rico to Chicago from $117

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 10/29. 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

Recent one-way flight deals from Puerto Rico to Chicago

Recent last minute flight deals from Puerto Rico to Chicago

Recent direct flight deals from Puerto Rico to Chicago

Spirit Airlines flights from Puerto Rico to Chicago

Our best Spirit Airlines 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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Use the filters below to find and compare flights from Puerto Rico to Chicago that are best for you.

See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $225. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $270.

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 $253. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $480.

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 5% 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?

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

What airlines fly to Chicago?

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

The number of flights available between Puerto Rico and Chicago is 3 per day as of September 2025. The most frequent departure time is 3:00PM, with 84% of daily flights leaving in the afternoon.

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

25 flights are operational weekly from Puerto Rico to Chicago as of September 2025. The most popular departure day for this route is Mon, 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