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$203+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$379
(Southwest)

One-way from

$203
(Southwest)

Popular in

January

Cheapest in

March

Average price

$650
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. 27% potential increase in price ($252 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 6/10$379
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sun 7/207:30 amSJO - MDW
2 stops29h 34mMultiple Airlines
Mon 7/282:54 pmMDW - SJO
2 stops13h 41mMultiple Airlines
Deal found 6/11$485
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 10/81:13 pmSJO - MDW
1 stop7h 31mDelta
Wed 10/156:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 6/12$680
This eDestinos deal was found by Cheapflights users on 6/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/91:07 pmSJO - MDW
3 stops26h 16mAeromexico
Wed 10/156:00 amMDW - SJO
2 stops18h 36mAeromexico
Deal found 6/10$1,048
This LATAM Airlines deal was found by Cheapflights users on 6/11. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:00 pmSJO - MDW
2 stops15h 51mLATAM Airlines
Tue 9/3010:35 amMDW - SJO
2 stops30h 00mLATAM Airlines
Deal found 6/11$2,085

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 June 12, 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

Tue 8/26

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Sat 8/30

10:10 am-6:55 pm

1 stop9h 45m

$379

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 7/20

7:30 am-2:04 pm

2 stops29h 34m

Chicago Midway

Mon 7/28

2:54 pm-3:35 am

2 stops13h 41m

$485

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 7/29

1:21 pm-11:58 am

1 stop21h 37m

Chicago Midway

Sat 8/2

6:00 am-1:05 pm

1 stop8h 05m

$1,234

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 8/26

1:40 pm-11:20 pm

1 stop8h 40m

$203

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/9

6:07 pm-1:47 pm

3 stops18h 40m

$254

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 7/11

1:21 pm-9:45 am

1 stop19h 24m

$970

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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.

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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $379, Southwest will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Delta for as low as $1,234. Users have found that Southwest 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 San José?

Book flights to San José if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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