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$196+ Cheap flights from San José (SJO) 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from San José to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) 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 29, 2025.

Round-trip from

$369
(Kiwi.com)

One-way from

$196
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$594
From San José Juan Santamaria Intl to Chicago Midway
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One-way flight from San José Juan Santamaria Intl to Chicago Midway
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Highest demand for flights based on searches. 28% potential increase in price ($265 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($36 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 José to Midway

Cheapest flights from San José to Midway
Explore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/2211:27 amSJO - MDW
1 stop21h 27mMultiple Airlines
Mon 8/254:24 pmMDW - SJO
1 stop19h 08mMultiple Airlines
Deal found 7/27$369
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:47 pmSJO - MDW
1 stop23h 00mFrontier
Sat 8/236:10 amMDW - SJO
1 stop7h 14mFrontier
Deal found 7/29$372
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/241:40 pmSJO - MDW
1 stop8h 40mSouthwest
Tue 9/306:25 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 7/29$384

Cheapflights Fare Finder

 
Customize your flight search to find flights from San José 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 29, 2025.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.

Fly from

San José

Fly to

Midway

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 8/22

11:27 am-9:54 am

1 stop21h 27m

Chicago Midway

Mon 8/25

4:24 pm-10:32 am

1 stop19h 08m

$369

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/16

1:47 pm-1:47 pm

1 stop23h 00m

Chicago Midway

Sat 8/23

6:10 am-12:24 pm

1 stop7h 14m

$372

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

8:50 am-6:25 pm

1 stop8h 35m

Chicago Midway

Tue 9/30

9:10 am-6:55 pm

1 stop10h 45m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 8/20

11:27 am-10:08 am

2 stops21h 41m

$196

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/2

1:47 pm-1:47 pm

1 stop23h 00m

$231

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/2

8:45 am-6:50 pm

2 stops9h 05m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from San José to Midway

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

What is the cheapest time of day to fly from SJO to MDW?

Find hourly flight availability from San José 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 29, 2025.

When flying from San José, San José Province to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 32% versus 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 29, 2025.
Read through reviews of airlines operating flights from San José to Chicago Midway Airport, such as Southwest and Frontier. 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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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 José to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José to Chicago Midway?

    San José Juan Santamaria Intl (SJO), located 8.8 mi from the city center, is the airport you fly out of when you book flights from San José to Chicago Midway. 0 airlines have flights from Juan Santamaria Intl to Chicago Midway on a regular basis. Booking flights from San José Juan Santamaria Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    Currently priced at $372, Frontier will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $384. Users have found that Frontier is 44% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San José 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 José, San José Province to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San José, San José Province to Chicago Midway Airport (average of $160). Flying from San José, San José Province 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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