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$114+ 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 10/29. 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
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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 September 15, 2025.

Round-trip from

$227
(Southwest)

One-way from

$114
(Southwest)

Popular in

December

Cheapest in

November

Average price

$398
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 ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/174:35 pmMDW - SJU
1 stop6h 15mSouthwest
Tue 10/212:45 pmSJU - MDW
1 stop9h 00mSouthwest
Deal found 9/15$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 9/15. 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 10/168:25 amMDW - SJU
1 stop15h 04mFrontier
Tue 10/216:22 amSJU - MDW
1 stop18h 03mFrontier
Deal found 9/15$251
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
Thu 10/212:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 9/14$255

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 September 15, 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

Sat 10/18

2:35 pm-11:45 pm

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:05 pm-9:55 pm

1 stop9h 50m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/21

10:35 am-9:59 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:15 am-3:26 pm

1 stop9h 11m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

5:50 pm-9:50 am

2 stops15h 00m

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

Sat 11/15

6:40 am-5:25 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 11/25

6:05 am-10:50 am

1 stop6h 45m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 11/5

2:25 pm-12:35 am

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Wed 11/12

9:40 am-7:25 pm

1 stop11h 45m

$292

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

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

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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/6

10:12 am-2:54 am

1 stop14h 42m

San Juan Luis Munoz Marin Intl

Sun 11/9

3:59 am-2:31 pm

1 stop12h 32m

$354

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 11/11

6:40 am-6:35 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Tue 11/25

6:05 am-10:50 am

1 stop6h 45m

$355

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 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 September 12, 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 September 15, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 34% 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 September 15, 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
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

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 San Juan. 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 San Juan?

    Southwest and Delta can get you from Chicago Midway Airport to San Juan in just under 8h 10m. Your travel time can differ by up to 2h 14m. Airlines will cover a distance of 2057 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

  • What are the cheapest flights from Chicago Midway Airport to San Juan?

    The cheapest flight price from Chicago Midway Airport to San Juan is $464. On average you can expect to pay $573. The most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), can usually be booked for $227.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 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%

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