How often are flights from Chicago to Puerto Rico delayed?

Historically, on average around 28% 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 128 minutes.

What airlines fly to Puerto Rico?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Puerto Rico from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 3 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.

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

As of July 2026, there are 2 flights per week flying from Chicago Midway Airport to Puerto Rico. The most common day of the week flights depart is Sat, with 50% of flights taking off on this day.

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

Wednesday 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.

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

Southwest is the most popular carrier operating from Chicago Midway to Puerto Rico

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

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 27% of their flights experiencing any sort of delay.

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

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

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

Prices for flights from Chicago Midway Airport to Puerto Rico are refreshed on a daily basis.

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

As of July 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to Puerto Rico.

How old do you have to be to fly from Chicago Midway 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 Midway Airport to Puerto Rico.

What documentation or ID do you need to fly to Puerto Rico?

The necessary travel and health documents for your Puerto Rico 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.

$128 Cheap Flights from Chicago Midway Airport to Puerto Rico in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Puerto Rico

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:45 pm - 10:00 pm

MDW

SJU

8h 15m

2 stops

6:00 am - 2:30 pm

SJU

MDW

9h 30m

2 stops

$256Southwest

Tue, Sep 1 - Fri, Sep 4

8:30 am - 4:25 pm

MDW

SJU

6h 55m

1 stop

8:55 pm - 8:45 am

SJU

MDW

12h 50m

1 stop

$256Southwest

Tue, Aug 25 - Thu, Aug 27

6:15 am - 1:35 pm

MDW

SJU

6h 20m

1 stop

8:55 pm - 11:25 am

SJU

MDW

15h 30m

2 stops

$256Southwest

Tue, Aug 25 - Thu, Aug 27

12:46 pm - 10:29 pm

MDW

SJU

8h 43m

1 stop

7:00 am - 3:44 pm

SJU

MDW

9h 44m

1 stop

$316Delta

Tue, Aug 25 - Tue, Sep 1

12:46 pm - 10:29 pm

MDW

SJU

8h 43m

1 stop

7:00 am - 3:44 pm

SJU

MDW

9h 44m

1 stop

$316Delta

Wed, Aug 26 - Tue, Sep 1

11:35 am - 10:19 pm

MDW

SJU

9h 44m

1 stop

2:59 pm - 10:45 pm

SJU

MDW

8h 46m

1 stop

$351Delta

Fri, Sep 11 - Thu, Sep 17

6:25 am - 3:19 pm

MDW

SJU

7h 54m

1 stop

6:30 am - 5:51 pm

SJU

MDW

12h 21m

1 stop

$366Frontier

Wed, Sep 23 - Wed, Sep 30

6:25 am - 3:19 pm

MDW

SJU

7h 54m

1 stop

6:30 am - 5:51 pm

SJU

MDW

12h 21m

1 stop

$368Frontier

Wed, Sep 9 - Wed, Sep 16

4:45 pm - 5:02 am

MDW

SJU

11h 17m

1 stop

6:00 am - 2:59 pm

SJU

MDW

33h 59m

2 stops

$427Multiple Airlines

Wed, Aug 12 - Sun, Aug 16

9:29 am - 2:33 am

MDW

SJU

15h 04m

2 stops

7:04 pm - 12:59 pm

SJU

MDW

19h 55m

1 stop

$755Multiple Airlines

Mon, Nov 23 - Mon, Nov 30

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Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets

Frontier

Sep 9

MDW6:25 amChicago Midway

7h 54m

1 stop

SJU3:19 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU6:30 amSan Juan Luis Munoz Marin Intl

12h 21m

1 stop

MDW5:51 pmChicago Midway

$368

Frontier

Sep 18

MDW6:25 amChicago Midway

7h 54m

1 stop

SJU3:19 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU6:30 amSan Juan Luis Munoz Marin Intl

12h 21m

1 stop

MDW5:51 pmChicago Midway

$402

Frontier

Aug 12

MDW4:45 pmChicago Midway

11h 17m

1 stop

SJU5:02 amSan Juan Luis Munoz Marin Intl

Aug 17

SJU6:32 amSan Juan Luis Munoz Marin Intl

11h 50m

1 stop

MDW5:22 pmChicago Midway

$406

Southwest flights from Chicago Midway Airport to Puerto Rico

Our best Southwest deals on Chicago Midway Airport to Puerto Rico flight tickets

Southwest

Aug 25

MDW7:30 amChicago Midway

10h 30m

1 stop

SJU7:00 pmSan Juan Luis Munoz Marin Intl

Aug 30

SJU9:25 pmSan Juan Luis Munoz Marin Intl

13h 35m

1 stop

MDW10:00 amChicago Midway

$256

Southwest

Sep 23

MDW12:50 pmChicago Midway

8h 15m

2 stops

SJU10:05 pmSan Juan Luis Munoz Marin Intl

Sep 27

SJU9:25 pmSan Juan Luis Munoz Marin Intl

12h 20m

1 stop

MDW8:45 amChicago Midway

$274

Southwest

Aug 26

MDW12:20 pmChicago Midway

8h 40m

1 stop

SJU10:00 pmSan Juan Luis Munoz Marin Intl

Sep 1

SJU1:20 pmSan Juan Luis Munoz Marin Intl

6h 50m

1 stop

MDW7:10 pmChicago Midway

$286

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/1

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Fri 9/4

6:00 am-2:30 pm

2 stops9h 30m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/25

8:30 am-4:25 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Thu 8/27

8:55 pm-8:45 am

1 stop12h 50m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/25

6:15 am-1:35 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Thu 8/27

8:55 pm-11:25 am

2 stops15h 30m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/25

12:46 pm-10:29 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:00 am-3:44 pm

1 stop9h 44m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/26

12:46 pm-10:29 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:00 am-3:44 pm

1 stop9h 44m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/11

11:35 am-10:19 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Thu 9/17

2:59 pm-10:45 pm

1 stop8h 46m

$351

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/23

6:25 am-3:19 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Wed 9/30

6:30 am-5:51 pm

1 stop12h 21m

$366

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/9

6:25 am-3:19 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Wed 9/16

6:30 am-5:51 pm

1 stop12h 21m

$368

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/12

4:45 pm-5:02 am

1 stop11h 17m

San Juan Luis Munoz Marin Intl

Sun 8/16

6:00 am-2:59 pm

2 stops33h 59m

$427

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/23

9:29 am-2:33 am

2 stops15h 04m

San Juan Luis Munoz Marin Intl

Mon 11/30

7:04 pm-12:59 pm

1 stop19h 55m

$755

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 Midway 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 February, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $254.

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 Midway Airport is on a Sunday. momondo users have found tickets for Sunday departures for as low as $499. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $666.

What is the cheapest Chicago Midway to Puerto Rico flight route?

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

How far in advance should I book a flight from Chicago Midway Airport to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $399 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 Midway Airport for as low as $326 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to Puerto Rico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago Midway Airport to Puerto Rico flight deals and tips

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

Best Price Found	$542
Fastest flight time	4h 40m
Direct flights	Mon and Sun
Airports in Puerto Rico	20 airports

The best flight deal from Chicago Midway Airport to Puerto Rico found on momondo in the last 72 hours is $542

The fastest flight from Chicago Midway Airport to Puerto Rico takes 4h 40m

Direct flights go from Chicago Midway Airport to Puerto Rico on Monday and Sunday. There are no airlines offering direct flights.

There are 20 airports in Puerto Rico. From Chicago Midway Airport there are direct flights to San Juan Luis Munoz Marin Intl (SJU).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Puerto Rico

When did momondo last update prices for flights from Chicago Midway Airport to Puerto Rico?
Prices for flights from Chicago Midway Airport to Puerto Rico are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Puerto Rico?
As of July 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to Puerto Rico.
How old do you have to be to fly from Chicago Midway 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 Midway Airport to Puerto Rico.
What documentation or ID do you need to fly to Puerto Rico?
The necessary travel and health documents for your Puerto Rico 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 Chicago Midway Airport to Puerto Rico?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Puerto Rico is Airbus A321-100/200 (20.93% of total bookings). The next most popular plane models are Airbus A321 (sharklets) (16.28%), Boeing 737 MAX 8 (11.63%), and Airbus A321neo (11.63%).

Best airlines flying from Chicago Midway Airport to Puerto Rico

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $91	Free Cancellation	Rating 5.6 2,755 reviews	Search Frontier flights
Delta	PriceFrom $132	Free Cancellation	Rating 7.8 8,483 reviews	Search Delta flights
Southwest	PriceFrom $346	Free Cancellation	Rating 8.0 4,229 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?

Flights from Chicago to Puerto Rico 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 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?

If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from Chicago and alert you when they change.

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.

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Complete your trip

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Popular cities in Puerto Rico

Flights to San Juanfrom $98

Flights to Aguadillafrom $221

Flights to Poncefrom $254

Flights to Culebrafrom $354

Flights to Mayagüezfrom $380

Cheap flights from Chicago Midway Airport to Puerto Rico from $128

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Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets

Southwest flights from Chicago Midway Airport to Puerto Rico

Our best Southwest deals on Chicago Midway Airport to Puerto Rico flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway 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 Midway 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 Chicago Midway to Puerto Rico flight route?

How far in advance should I book a flight from Chicago Midway Airport to Puerto Rico?

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

What is the cheapest airline that flies from Chicago Midway 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 Midway Airport to Puerto Rico on average per week?

Cheap Chicago Midway Airport to Puerto Rico flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Puerto Rico

Frequently asked questions about flying from Chicago Midway Airport to Puerto Rico

Best airlines flying from Chicago Midway Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago Midway 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

Popular flights according to clicks in the last 7 days on momondo

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Puerto Rico flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Puerto Rico

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Puerto Rico

List of cabin classes available on flights landing in Puerto Rico. Availability may vary depending on flight origin and airline.

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According to popular flight searches on momondo this year