HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$108+ Cheap flights from Midway (MDW) to Puerto Rico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Puerto Rico

Cheapest flights from Midway to Puerto Rico
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Sun 1/1110:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/29$336
This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Fri 1/95:45 amSJU - MDW
1 stop10h 21mFrontier
Deal found 12/29$348
This CheapOair deal was found by Cheapflights users on 12/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - SJU
1 stop13h 39mFrontier
Tue 1/134:35 pmSJU - MDW
1 stop7h 44mFrontier
Deal found 12/31$374
This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Mon 1/57:06 pmSJU - MDW
2 stops29h 11mFrontier
Deal found 12/29$396
This Priceline deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Thu 1/84:39 pmSJU - MDW
1 stop7h 38mFrontier
Deal found 12/29$413
This Kiwi.com deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop25h 41mMultiple Airlines
Wed 1/78:00 amSJU - MDW
2 stops29h 31mMultiple Airlines
Deal found 12/30$415
This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mMultiple Airlines
Tue 1/612:53 pmSJU - MDW
1 stop27h 13mMultiple Airlines
Deal found 12/29$441
This Frontier deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:10 pmMDW - SJU
1 stop9h 40mFrontier
Thu 1/84:39 pmSJU - MDW
1 stop7h 38mFrontier
Deal found 12/29$443
This Frontier deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:10 pmMDW - SJU
1 stop9h 40mFrontier
Fri 1/95:45 amSJU - MDW
1 stop10h 21mFrontier
Deal found 12/29$447
This Trip.com deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - SJU
1 stop13h 39mFrontier
Sat 1/109:23 pmSJU - MDW
1 stop27h 36mFrontier
Deal found 12/30$461

Find flight deals from Midway to Puerto Rico

Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated December 31, 2025.

Round-trip from

$194
(Trip.com)

One-way from

$108
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$562
From Chicago Midway to Puerto Rico
Search Deals
One-way flight from Chicago Midway to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 31, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Midway

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Thu 1/22

7:30 am-11:59 am

1 stop6h 29m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/22

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:22 pm

1 stop8h 27m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Sat 1/24

6:15 am-3:38 pm

1 stop11h 23m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

8:30 am-5:05 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Wed 1/21

9:05 am-6:35 pm

1 stop11h 30m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/28

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:40 am-12:30 pm

2 stops8h 50m

$310

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/28

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

9:05 am-6:35 pm

1 stop11h 30m

$355

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

5:00 am-2:55 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Mon 2/2

6:10 am-1:55 pm

2 stops9h 45m

$385

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Sat 1/24

6:00 am-1:40 pm

2 stops9h 40m

$390

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/10

8:20 am-2:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Fri 1/16

7:00 am-6:35 pm

1 stop13h 35m

$391

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/21

2:10 pm-11:55 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Fri 2/27

5:30 am-1:30 pm

2 stops10h 00m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 20 results
1
2

Best time to book a flight from Midway to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Puerto Rico

What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $133). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to PR?

Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Puerto Rico as you normally would.

How often are flights from Chicago to Puerto Rico delayed?

About 23% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 97 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

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

Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated December 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,013 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,069 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Puerto Rico?

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Puerto Rico in about 6h 35m. The time it takes to get you to your destination can typically vary by up to 4h 22m. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Midway to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Puerto Rico.

  • Can I find deals for business class flights from Midway to Puerto Rico?

    Yes. Cheapflights offers flight deals from Midway to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $133). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
O'Hare Intl to Bridgetown flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Ponce flights
O'Hare Intl to St. John's flights
Midway to Santo Domingo flights
Midway to George Town flights
O'Hare Intl to Aguadilla flights
Midway to Simpson Bay flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kingston flights
O'Hare Intl to Road Town flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to The Valley flights
Midway to Castries flights
O'Hare Intl to Havana flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Kingstown flights
Midway to Kingston flights
O'Hare Intl to Castries flights
Midway to Santiago de los Caballeros flights
Midway to St. John's flights
O'Hare Intl to Fort-de-France flights

Top 3 airlines flying from Midway to Puerto Rico

Discover the top 3 airlines that operate flights from Midway to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$325Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$487FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights