HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$114+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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

Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated September 15, 2025.

Round-trip from

$227
(Southwest)

One-way from

$114
(Southwest)

Popular in

December

Cheapest in

October

Average price

$380
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. 8% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:50 pmMDW - SJU
2 stops15h 00mSouthwest
Tue 10/212:45 pmSJU - MDW
1 stop9h 00mSouthwest
Deal found 9/14$227
This Frontier deal was found by Cheapflights users on 9/12. 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.
Fri 10/36:21 amMDW - SJU
1 stop8h 01mFrontier
Mon 10/69:26 pmSJU - MDW
2 stops17h 12mFrontier
Deal found 9/12$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 11/149:15 amMDW - SJU
1 stop13h 26mFrontier
Sun 11/162:11 amSJU - MDW
1 stop14h 22mFrontier
Deal found 9/14$237
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/238:25 amMDW - SJU
1 stop15h 04mFrontier
Sun 10/262:12 amSJU - MDW
1 stop21h 51mFrontier
Deal found 9/13$240
This Frontier deal was found by Cheapflights users on 9/14. 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.
Mon 10/2010:33 amMDW - SJU
1 stop8h 23mFrontier
Sat 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
Deal found 9/14$244
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/1712:13 pmMDW - SJU
1 stop11h 16mFrontier
Tue 10/211:59 amSJU - MDW
1 stop30h 26mFrontier
Deal found 9/13$246
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/1710:33 amMDW - SJU
1 stop8h 23mFrontier
Sun 10/195:30 amSJU - MDW
1 stop29h 03mFrontier
Deal found 9/14$247
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 9/218:06 amMDW - SJU
1 stop14h 17mFrontier
Sat 9/2712:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 9/13$253
This Frontier deal was found by Cheapflights users on 9/14. 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.
Fri 9/265:15 pmMDW - SJU
2 stops15h 41mFrontier
Fri 10/37:15 amSJU - MDW
1 stop9h 45mFrontier
Deal found 9/14$255
This Frontier deal was found by Cheapflights users on 9/14. 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 9/232:32 pmMDW - SJU
2 stops18h 24mFrontier
Sat 9/273:16 pmSJU - MDW
1 stop9h 01mFrontier
Deal found 9/14$256

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 September 15, 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

Wed 11/5

10:40 am-10:05 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 11/12

9:40 am-7:25 pm

1 stop11h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

4:35 pm-11:50 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Tue 10/21

2:45 pm-10:45 pm

1 stop9h 00m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 11/9

6:15 am-3:14 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Mon 11/10

4:31 pm-10:11 pm

1 stop7h 40m

$272

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 11/11

10:40 am-10:05 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 11/14

6:40 am-11:25 am

1 stop6h 45m

$292

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/3

6:30 am-2:44 am

2 stops18h 14m

San Juan Luis Munoz Marin Intl

Mon 11/10

4:31 pm-10:11 pm

1 stop7h 40m

$305

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/18

2:50 pm-11:25 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 10/20

8:20 pm-9:10 am

1 stop13h 50m

$311

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 11/9

6:30 am-8:44 pm

1 stop12h 14m

San Juan Luis Munoz Marin Intl

Sun 11/9

3:59 am-8:31 pm

1 stop18h 32m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/26

6:21 am-3:22 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Mon 9/29

9:26 pm-3:58 pm

2 stops19h 32m

$323

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 11/11

9:20 am-11:20 pm

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Tue 11/25

6:05 am-10:50 am

1 stop6h 45m

$336

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/9

4:35 pm-11:50 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Mon 10/13

1:05 pm-9:55 pm

1 stop9h 50m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 19 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $339). 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 September 15, 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.

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 September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines 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
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Southwest and Frontier fly from Chicago Midway Airport to Puerto Rico in about 6h 59m. The time it takes to get you to your destination can typically vary by up to 2h 26m. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago Midway Airport to Puerto Rico?

    Looking for the cheapest flight from Chicago Midway Airport to Puerto Rico? While on average our users pay $573, our data indicates the cheapest price to be $464. The most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl), is priced around $227.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $339). 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 Montego Bay 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
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Bridgetown flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Providenciales flights
O'Hare Intl to Road Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Kingston flights
Midway to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Freeport flights
O'Hare Intl to St. George's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Castries flights
O'Hare Intl to Basseterre flights
Midway to Kingston flights
O'Hare Intl to Havana flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Ponce flights
O'Hare Intl to The Valley flights
O'Hare Intl to Gregory Town flights
Midway to St. John's flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Fort-de-France flights

Top 5 airlines flying from Midway to Puerto Rico

Discover the top 5 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$283FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$412FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$364Average$494FlexibilityNo 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.