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$145+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from San Juan to Chicago Midway are usually found in December or August, 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 April 22, 2025.

Round-trip from

$294
(Cheapflightsfares)

One-way from

$145
(Mytrip)

Popular in

June

Cheapest in

December

Average price

$489
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. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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.
Fri 5/26:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/56:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/21$294
This Delta deal was found by Cheapflights users on 4/21. 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.
Thu 10/27:30 amSJU - MDW
1 stop8h 24mDelta
Mon 10/66:00 amMDW - SJU
1 stop6h 23mDelta
Deal found 4/21$344
This Southwest deal was found by Cheapflights users on 4/21. 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 10/95:50 amSJU - MDW
2 stops8h 30mSouthwest
Tue 10/147:40 amMDW - SJU
2 stops8h 35mSouthwest
Deal found 4/21$381
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Tue 6/172:36 amSJU - MDW
3 stops15h 18mMultiple Airlines
Tue 6/249:40 amMDW - SJU
3 stops24h 08mMultiple Airlines
Deal found 4/21$709

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 April 22, 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

Fri 5/2

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Mon 5/5

6:15 am-2:47 pm

1 stop7h 32m

$294

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/2

7:30 am-2:54 pm

1 stop8h 24m

Chicago Midway

Mon 10/6

6:00 am-1:23 pm

1 stop6h 23m

$344

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

Tue 10/14

6:55 am-5:15 pm

1 stop9h 20m

$381

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 6/17

2:36 am-4:54 pm

3 stops15h 18m

Chicago Midway

Tue 6/24

9:40 am-10:48 am

3 stops24h 08m

$709

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/8

3:56 am-12:24 pm

1 stop9h 28m

$145

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/30

12:36 pm-10:14 pm

1 stop10h 38m

$151

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/31

1:00 pm-5:20 pm

Nonstop5h 20m

$186

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/24

7:30 am-3:20 pm

1 stop8h 50m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

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 April 18, 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 April 22, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 22, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from San Juan to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $294. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $401 and $433, respectively. You may be able to fly from San Juan to Chicago Midway Airport for 19% less than the average price by searching for these airlines.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $145. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from San Juan to Chicago Midway Airport for a low price.

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

    Looking at all options, your cheapest flight can be booked for $132. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $271 on average our data indicates $323 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 San Juan?

Book flights to San Juan if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$278FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$435FlexibilityNo cancel feeOn-time63%

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