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$113+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from San Juan to Chicago Midway are usually found in December or October, booked 45 days in advance, depart on a Tuesday or Monday and return on a Monday

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 July 31, 2025.

Round-trip from

$234
(SmartFares)

One-way from

$113
(Cheapflightsfares)

Popular in

March

Cheapest in

December

Average price

$467
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. 12% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
Sat 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:19 pmSJU - MDW
3 stops26h 24mMultiple Airlines
Mon 9/1512:50 pmMDW - SJU
3 stops24h 21mMultiple Airlines
Deal found 7/29$321
This Southwest deal was found by Cheapflights users on 7/31. 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 9/111:20 pmSJU - MDW
1 stop10h 10mSouthwest
Tue 9/167:40 amMDW - SJU
1 stop8h 45mSouthwest
Deal found 7/31$351
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:58 pmSJU - MDW
1 stop9h 12mDelta
Tue 10/76:00 amMDW - SJU
1 stop6h 19mDelta
Deal found 7/31$361

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 July 31, 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

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

3:19 pm-4:43 pm

3 stops26h 24m

Chicago Midway

Mon 9/15

12:50 pm-2:11 pm

3 stops24h 21m

$321

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/16

9:00 am-7:45 pm

2 stops9h 45m

$351

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

12:58 pm-9:10 pm

1 stop9h 12m

Chicago Midway

Tue 10/7

6:00 am-1:19 pm

1 stop6h 19m

$361

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-9:51 am

1 stop7h 12m

$113

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/4

3:19 pm-4:43 pm

3 stops26h 24m

$163

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/8

2:20 pm-5:35 pm

Nonstop5h 15m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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

How far ahead should I book a flight from San Juan to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Juan to Midway. Price data was last updated on July 25, 2025.

The best time to book flights from San Juan to Chicago Midway Airport is 44 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 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 July 31, 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 July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $234. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $351 and $361, respectively. You may be able to fly from San Juan to Chicago Midway Airport for 42% 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 $162. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $258 on average our data indicates $256 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
Valparaiso
Chesterton

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$459FlexibilityNo cancel feeOn-time63%

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