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$124+ Cheap flights from Midway (MDW) to San Juan

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 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Juan are usually found in November or May, booked 51 days in advance, depart on a Monday or Tuesday and return on a Tuesday

Cheap flight deals from Midway to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$258
(Priceline)

One-way from

$124
(Trip.com)

Popular in

December

Cheapest in

November

Average price

$404
From Chicago Midway to San Juan
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One-way flight from Chicago Midway to San Juan
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 San Juan

Cheapest flights from Midway to San Juan
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 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 8/13. 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.
Fri 9/128:15 amMDW - SJU
1 stop14h 08mFrontier
Sat 9/203:16 pmSJU - MDW
1 stop9h 01mFrontier
Deal found 8/13$267
This FlightHub 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 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 8/12$268
This FlightHub 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 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 8/12$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 8/12. 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.
Mon 9/156:20 amMDW - SJU
1 stop6h 51mFrontier
Wed 9/1712:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 8/12$274
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:21 amMDW - SJU
1 stop7h 16mFrontier
Fri 11/78:03 amSJU - MDW
1 stop6h 41mFrontier
Deal found 8/11$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
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.
Thu 9/258:15 amMDW - SJU
1 stop14h 08mFrontier
Sun 9/2812:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 8/13$280

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Juan 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 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.

Fly from

Midway

Fly to

San Juan

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

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

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

Fri 10/31

10:40 am-9:59 pm

1 stop10h 19m

San Juan Luis Munoz Marin Intl

Wed 11/5

3:36 pm-10:14 pm

1 stop8h 38m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/18

6:15 am-2:38 pm

1 stop7h 23m

San Juan Luis Munoz Marin Intl

Sun 10/26

9:19 pm-4:20 pm

1 stop20h 01m

$267

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 13 results
1
2

Best time to book a flight from Midway to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan

How far ahead should I book a flight from Chicago Midway Airport to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on August 8, 2025.

The best time to book flights from Chicago Midway Airport to San Juan is 51 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $254). Flying from Chicago Midway Airport to San Juan 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 SJU?

Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 31% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Juan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated August 14, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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
8,045 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

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 San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Juan round-trip?

    Frontier, at $133, was found to be the cheapest airline from Chicago Midway Airport to San Juan.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines. You may be able to fly from Chicago Midway Airport to San Juan for 68% less than the average price by searching for these airlines.

  • Can I find deals for flights from Midway to San Juan that include hotel bookings?

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

  • How can I find direct flights from Midway to San Juan?

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

  • Can I find deals for business class flights from Midway to San Juan?

    Yes. Cheapflights offers flight deals from Midway to San Juan 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 San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $254). Flying from Chicago Midway Airport to San Juan 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

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Top 5 airlines flying from Midway to San Juan

Discover the top 5 airlines that operate flights from Midway to San Juan. 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 14, 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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