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$125+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Juan are usually found in May or October, 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 November 21, 2025.

Round-trip from

$211
(Priceline)

One-way from

$125
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$387
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. 4% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 21, 2025.

This Priceline deal was found by Cheapflights users on 11/20. 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.
Sun 12/72:59 pmMDW - SJU
1 stop6h 51mFrontier
Wed 12/103:55 amSJU - MDW
1 stop20h 03mFrontier
Deal found 11/20$216
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/123:52 pmMDW - SJU
1 stop30h 24mMultiple Airlines
Mon 12/157:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 11/20$229
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/42:16 pmMDW - SJU
1 stop18h 16mFrontier
Wed 12/107:10 amSJU - MDW
1 stop31h 51mFrontier
Deal found 11/20$231
This Priceline deal was found by Cheapflights users on 11/19. 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 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Thu 12/113:55 amSJU - MDW
1 stop20h 44mFrontier
Deal found 11/19$236
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/32:49 pmMDW - SJU
2 stops19h 43mMultiple Airlines
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mMultiple Airlines
Deal found 11/19$239
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/113:10 pmMDW - SJU
1 stop16h 45mFrontier
Mon 12/151:59 amSJU - MDW
2 stops32h 47mFrontier
Deal found 11/19$244
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/113:10 pmMDW - SJU
1 stop16h 45mFrontier
Sun 12/141:59 amSJU - MDW
2 stops22h 13mFrontier
Deal found 11/18$246
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Sat 12/62:59 pmMDW - SJU
1 stop26h 51mMultiple Airlines
Wed 12/107:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 11/20$247
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Thu 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/20$249
This Priceline deal was found by Cheapflights users on 11/19. 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 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Sun 12/143:55 amSJU - MDW
1 stop20h 03mFrontier
Deal found 11/19$252

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 November 21, 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 1/24

10:46 am-11:45 pm

1 stop10h 59m

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 1/13

11:21 am-11:45 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:15 pm-10:07 pm

1 stop9h 52m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

6:00 am-2:31 pm

1 stop6h 31m

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

Mon 1/19

10:46 am-11:45 pm

1 stop10h 59m

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

Sun 1/11

6:45 am-5:17 pm

1 stop8h 32m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:15 pm-10:07 pm

1 stop9h 52m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/27

6:00 am-2:31 pm

1 stop6h 31m

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

Wed 2/4

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

9:05 am-6:35 pm

1 stop11h 30m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 12/3

4:35 pm-12:35 am

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Tue 12/9

6:40 am-1:45 pm

1 stop9h 05m

$270

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-1:55 pm

2 stops9h 45m

$270

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/5

6:10 am-9:50 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-1:40 pm

2 stops9h 40m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 23 results
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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 November 14, 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $127). Flying from Chicago Midway Airport to San Juan 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 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 November 21, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Juan in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying at noon, 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. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How often are flights from Chicago to San Juan delayed?

About 22% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 96 minutes.

What is the most punctual flight time for Chicago to San Juan 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 San Juan flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 22% of flights being delayed.

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 November 21, 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
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
9,029 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
8,158 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
3,103 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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?

    Delta can get you from Chicago Midway Airport to San Juan in just under 10h 59m. Your travel time can differ by up to . Airlines will cover a distance of 2057 mi.

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

    Frontier, at $144, 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 65% 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $127). Flying from Chicago Midway Airport to San Juan 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

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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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$380Average$503FlexibilityNo cancel feeOn-time63%

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