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$137+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 2, 2025.

Round-trip from

$296
(Frontier)

One-way from

$137
(Trip.com)

Popular in

April

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. 13% potential increase in price ($54 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 2, 2025.

This Flightnetwork deal was found by Cheapflights users on 3/31. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/26:00 amSJU - MDW
1 stop12h 28mFrontier
Mon 5/51:19 pmMDW - SJU
1 stop12h 32mFrontier
Deal found 3/31$281
This Delta deal was found by Cheapflights users on 3/31. 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.
Fri 5/97:30 amSJU - MDW
1 stop11h 13mDelta
Sat 5/1712:48 pmMDW - SJU
1 stop8h 59mDelta
Deal found 3/31$381
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 9/125:50 amSJU - MDW
1 stop10h 00mSouthwest
Mon 9/156:05 amMDW - SJU
1 stop8h 05mSouthwest
Deal found 4/1$395

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 2, 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-5:28 pm

1 stop12h 28m

Chicago Midway

Mon 5/5

1:19 pm-2:51 am

1 stop12h 32m

$281

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/9

7:30 am-5:43 pm

1 stop11h 13m

Chicago Midway

Sat 5/17

12:48 pm-7:48 pm

1 stop6h 00m

$381

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/10

1:00 pm-5:20 pm

Nonstop5h 20m

Chicago Midway

Sun 5/18

8:45 pm-9:50 am

1 stop12h 05m

$397

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/9

2:40 pm-4:40 pm

2 stops27h 00m

Chicago Midway

Tue 4/22

11:15 am-5:04 pm

3 stops28h 49m

$907

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:47 pm

1 stop14h 01m

$137

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/10

1:33 am-8:33 pm

1 stop20h 00m

$162

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 6/14

11:41 am-3:05 pm

1 stop28h 24m

$172

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/10

1:00 pm-5:20 pm

Nonstop5h 20m

$186

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/3

12:50 pm-10:22 pm

1 stop10h 32m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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 March 28, 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 2, 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 2, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Avelo Airlines 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
4,275 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,277 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $296. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $381 and $395, respectively. You may be able to fly from San Juan to Chicago Midway Airport for 16% 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 $137. However, be on the lookout for offers from Avelo Airlines and Southwest, 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 $324. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $231 on average our data indicates $433 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
New Buffalo
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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$264FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$438FlexibilityNo cancel feeOn-time63%

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