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Puerto Rico

$124+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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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 August 13, 2025.

Round-trip from

$258
(Priceline)

One-way from

$124
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$399
From Chicago Midway to Puerto Rico
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One-way flight from Chicago Midway to Puerto Rico
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Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 13, 2025.

This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:20 amMDW - SJU
1 stop6h 49mFrontier
Sat 10/254:18 pmSJU - MDW
1 stop8h 07mFrontier
Deal found 8/13$258
This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:51 amMDW - SJU
1 stop12h 08mFrontier
Thu 9/253:16 pmSJU - MDW
1 stop9h 04mFrontier
Deal found 8/12$260
This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:15 amMDW - SJU
1 stop7h 23mFrontier
Sun 10/269:19 pmSJU - MDW
1 stop20h 01mFrontier
Deal found 8/12$267
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:15 amMDW - SJU
1 stop6h 56mFrontier
Sat 10/114:18 pmSJU - MDW
1 stop8h 07mFrontier
Deal found 8/11$268
This Priceline deal was found by Cheapflights users on 8/11. 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.
Mon 10/66:20 amMDW - SJU
1 stop6h 51mFrontier
Sun 10/121:59 amSJU - MDW
1 stop16h 28mFrontier
Deal found 8/11$271
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:15 amMDW - SJU
1 stop14h 08mFrontier
Sat 9/273:16 pmSJU - MDW
1 stop9h 01mFrontier
Deal found 8/11$272
This Frontier deal was found by Cheapflights users on 8/12. 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.
Sat 9/610:51 amMDW - SJU
1 stop12h 08mFrontier
Sat 9/133:16 pmSJU - MDW
1 stop9h 01mFrontier
Deal found 8/12$273
This Frontier deal was found by Cheapflights users on 8/10. 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 9/86:20 amMDW - SJU
1 stop6h 51mFrontier
Wed 9/1712:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 8/10$274
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:15 amMDW - SJU
1 stop7h 00mFrontier
Thu 11/61:11 amSJU - MDW
1 stop8h 09mFrontier
Deal found 8/10$275
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/256:15 amMDW - SJU
1 stop7h 11mFrontier
Fri 9/57:15 amSJU - MDW
1 stop9h 45mFrontier
Deal found 8/13$277

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 August 13, 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

Mon 10/20

6:20 am-2:09 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

Sat 10/25

4:18 pm-11:25 pm

1 stop8h 07m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/20

10:51 am-11:59 pm

1 stop12h 08m

San Juan Luis Munoz Marin Intl

Thu 9/25

3:16 pm-11:20 pm

1 stop9h 04m

$260

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 10/6

4:35 pm-11:50 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Mon 10/13

5:50 am-1:20 pm

2 stops8h 30m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/21

6:00 am-4:33 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Fri 10/24

7:15 am-4:09 pm

1 stop9h 54m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/24

11:35 am-7:45 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Wed 10/1

5:00 am-12:05 pm

2 stops8h 05m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 9/18

3:20 pm-11:50 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Mon 9/22

5:00 am-12:50 pm

2 stops8h 50m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/20

10:51 am-8:56 pm

1 stop9h 05m

$124

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/4

6:15 am-2:11 pm

1 stop6h 56m

$125

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/27

6:15 am-2:11 pm

1 stop6h 56m

$125

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/18

6:15 am-2:38 pm

1 stop7h 23m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 11 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 August 13, 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 August 13, 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
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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

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Alternative routes for Midway to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$279FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$415FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$352Average$489FlexibilityNo cancel feeOn-time63%

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