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Midway

$117+ Cheap flights from San Juan to Midway (MDW)

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.
SJU — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from San Juan to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Midway (MDW). 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

$117
(Trip.com)

Popular in

July

Cheapest in

December

Average price

$384
From San Juan to Chicago Midway
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One-way flight from San Juan to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 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 San Juan to Midway

Cheapest flights from San Juan to Midway
Explore the most affordable flight options available from San Juan to Midway. 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 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:50 amSJU - MDW
2 stops8h 30mSouthwest
Mon 10/278:45 pmMDW - SJU
1 stop12h 10mSouthwest
Deal found 9/14$227
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 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
Fri 10/316:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/13$235
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.
Thu 10/166:22 amSJU - MDW
2 stops18h 24mFrontier
Mon 10/2010:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/14$244
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/69:26 pmSJU - MDW
2 stops17h 12mFrontier
Fri 10/1710:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/15$249
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/239:26 pmSJU - MDW
2 stops19h 32mFrontier
Fri 9/266:21 amMDW - SJU
1 stop8h 01mFrontier
Deal found 9/15$256
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.
Sat 9/2712:28 amSJU - MDW
1 stop7h 43mFrontier
Thu 10/28:15 amMDW - SJU
1 stop14h 08mFrontier
Deal found 9/13$257
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.
Wed 10/291:59 amSJU - MDW
1 stop13h 34mFrontier
Mon 11/36:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/13$262
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.
Wed 10/291:59 amSJU - MDW
1 stop13h 34mFrontier
Sun 11/25:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/14$263
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:28 amSJU - MDW
1 stop7h 43mFrontier
Sun 10/56:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 9/13$272

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to Midway 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 San Juan to Chicago Midway Airport that are best for you.

Fly from

San Juan

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

Fri 10/17

4:35 pm-11:50 pm

1 stop6h 15m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

Wed 10/29

9:15 am-8:45 pm

1 stop10h 30m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/30

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

Sun 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 11/12

6:40 am-1:45 pm

1 stop9h 05m

Chicago Midway

Sat 11/15

1:15 pm-11:00 pm

1 stop7h 45m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

Mon 10/27

8:45 pm-9:55 am

1 stop12h 10m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

Sun 10/26

6:55 am-3:50 pm

1 stop7h 55m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/24

12:02 pm-11:03 pm

1 stop12h 01m

Chicago Midway

Sun 10/26

6:20 am-2:09 pm

1 stop6h 49m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

3:19 pm-11:46 pm

1 stop9h 27m

Chicago Midway

Mon 10/27

9:45 am-11:29 pm

1 stop12h 44m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/4

9:40 am-7:25 pm

1 stop11h 45m

Chicago Midway

Sun 11/9

1:25 pm-12:35 am

2 stops9h 10m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/9

3:19 pm-11:46 pm

1 stop9h 27m

Chicago Midway

Sun 10/12

6:20 am-2:09 pm

1 stop6h 49m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 18 results
1
2

Best time to book a flight from San Juan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Juan 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 San Juan to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $160). Flying from San Juan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 SJU to MDW?

Find hourly flight availability from San Juan to Midway. 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.

A simple way to save on the total cost of your ticket is to fly from San Juan to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 62% on your trip compared to booking a flight at noon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown Southwest and Frontier from San Juan to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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 San Juan to Midway. 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 San Juan to Chicago Midway Airport?

    There are many flights that can get you from San Juan to Chicago Midway Airport in 9h 50m. Fly via Southwest to get the fastest option. San Juan and Chicago Midway Airport are separated by a distance of 2057 mi.

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

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $148. Another option worth looking into is Southwest, starting at $320 round trip. You may be able to fly from San Juan to Chicago Midway Airport for 64% less than the average price by searching for these airlines.

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

    Looking at all options, your cheapest flight can be booked for $191. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $227 on average, our data indicates $231 when flying from San Juan to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $160). Flying from San Juan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from San Juan to Midway

Discover the top 2 airlines that operate flights from San Juan to Midway. 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$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$320Average$497FlexibilityNo cancel feeOn-time63%

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