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$108+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Juan are usually found in May or January, 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 October 16, 2025.

Round-trip from

$211
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$394
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. 5% potential increase in price ($22 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 October 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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Tue 10/281:56 pmMDW - SJU
2 stops26h 58mFrontier
Fri 10/313:04 amSJU - MDW
1 stop8h 22mFrontier
Deal found 10/15$211
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Sat 10/2511:31 amMDW - SJU
1 stop13h 59mFrontier
Fri 10/313:04 amSJU - MDW
1 stop8h 22mFrontier
Deal found 10/16$215
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 11/116:26 pmMDW - SJU
1 stop21h 28mFrontier
Tue 11/189:00 amSJU - MDW
1 stop16h 55mFrontier
Deal found 10/14$216
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Wed 11/122:06 pmMDW - SJU
2 stops33h 26mMultiple Airlines
Wed 11/199:00 amSJU - MDW
1 stop28h 42mMultiple Airlines
Deal found 10/15$223
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Tue 10/215:56 pmMDW - SJU
1 stop31h 06mFrontier
Tue 10/289:00 amSJU - MDW
2 stops28h 41mFrontier
Deal found 10/16$225
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Sat 11/16:20 amMDW - SJU
1 stop6h 59mFrontier
Mon 11/36:17 pmSJU - MDW
1 stop31h 38mFrontier
Deal found 10/15$231
This Frontier deal was found by Cheapflights users on 10/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amMDW - SJU
2 stops14h 17mFrontier
Mon 11/174:24 pmSJU - MDW
1 stop7h 47mFrontier
Deal found 10/15$235
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 12/58:42 pmMDW - SJU
2 stops18h 51mMultiple Airlines
Wed 12/107:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 10/15$238
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Wed 10/292:06 pmMDW - SJU
2 stops26h 48mFrontier
Wed 11/56:17 pmSJU - MDW
1 stop31h 38mFrontier
Deal found 10/15$239
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 12/53:52 pmMDW - SJU
1 stop16h 03mFrontier
Wed 12/107:10 amSJU - MDW
1 stop31h 51mFrontier
Deal found 10/15$241
This Frontier deal was found by Cheapflights users on 10/16. 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.
Sat 11/811:36 amMDW - SJU
1 stop13h 18mFrontier
Thu 11/134:31 pmSJU - MDW
1 stop7h 32mFrontier
Deal found 10/16$245

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 October 16, 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

Sun 12/7

10:49 am-11:20 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:38 pm-11:49 pm

1 stop7h 11m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/11

1:10 pm-10:05 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$289

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/12

1:50 pm-10:00 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$314

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 12/6

1:15 pm-11:00 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Fri 12/12

6:40 am-2:10 pm

2 stops9h 30m

$314

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

12:55 pm-12:35 am

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Thu 12/11

5:45 am-12:45 pm

2 stops9h 00m

$314

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

10:49 am-11:20 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sun 12/21

6:30 am-4:24 pm

1 stop11h 54m

$329

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/13

1:15 pm-11:10 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Sat 1/17

5:30 am-1:40 pm

2 stops10h 10m

$329

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/8

9:20 am-11:20 pm

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Thu 12/18

3:30 pm-11:00 pm

2 stops9h 30m

$329

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/5

2:25 pm-12:35 am

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:40 am-1:00 pm

2 stops8h 20m

$340

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

Sun 12/7

5:40 am-2:15 pm

1 stop10h 35m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

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 October 10, 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 $133). 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 October 16, 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.

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 October 16, 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
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
8,982 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
8,099 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
3,137 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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 55m. Your travel time can differ by up to 3h 36m. 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 $142, 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 66% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Juan one-way?

    $108 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $132 and $132, respectively.

  • 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 $133). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$288FlexibilityNo 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$379Average$499FlexibilityNo cancel feeOn-time63%

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