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$118+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 18, 2025.

Round-trip from

$211
(CheapOair)

One-way from

$118
(Kiwi.com)

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 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/56:15 amMDW - SJU
2 stops16h 30mMultiple Airlines
Mon 12/87:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 11/16$218
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.
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Wed 1/77:26 pmSJU - MDW
2 stops18h 05mFrontier
Deal found 11/18$221
This Priceline deal was found by Cheapflights users on 11/17. 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
Wed 12/103:55 amSJU - MDW
1 stop20h 03mFrontier
Deal found 11/17$226
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 11/16$231
This Southwest deal was found by Cheapflights users on 11/16. 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.
Wed 12/109:20 amMDW - SJU
1 stop12h 00mSouthwest
Tue 12/169:40 amSJU - MDW
1 stop11h 50mSouthwest
Deal found 11/16$245
This Frontier deal was found by Cheapflights users on 11/16. 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 12/56:15 amMDW - SJU
1 stop7h 06mFrontier
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/16$246
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.
Mon 12/88:42 pmMDW - SJU
2 stops24h 43mMultiple Airlines
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mMultiple Airlines
Deal found 11/18$250
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/142:59 pmMDW - SJU
1 stop26h 51mMultiple Airlines
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mMultiple Airlines
Deal found 11/17$256
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/47:44 amMDW - SJU
1 stop30h 29mFrontier
Mon 12/87:10 amSJU - MDW
2 stops27h 36mFrontier
Deal found 11/17$257
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 stop8h 58mFrontier
Sun 12/1412:00 pmSJU - MDW
2 stops36h 18mFrontier
Deal found 11/17$258

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 18, 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

Tue 1/20

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:22 pm

1 stop8h 27m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

10:48 am-8:58 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:55 pm-10:22 pm

1 stop8h 27m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-12:10 pm

1 stop8h 40m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Fri 1/23

9:05 am-6:35 pm

1 stop11h 30m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

1:55 pm-12:35 am

2 stops8h 40m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:00 am-12:30 pm

2 stops8h 30m

$290

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-11:59 am

1 stop6h 29m

$310

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/5

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:15 am-3:23 pm

1 stop11h 08m

$311

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/5

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:20 pm-11:50 pm

1 stop11h 30m

$322

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Sun 2/1

5:35 am-12:30 pm

2 stops8h 55m

$340

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 11/25

12:47 pm-11:13 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Tue 12/2

6:38 pm-11:47 pm

1 stop7h 09m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 20 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 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 18, 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 18, 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
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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
7.9
Good
8,008 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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
9,015 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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
8,146 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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
3,103 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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 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 and Southwest can get you from Chicago Midway Airport to San Juan in just under 6h 40m. Your travel time can differ by up to 4h 17m. 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 $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

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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 18, 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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