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$153+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$313
(Kiwi.com)

One-way from

$153
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$529
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 ($267 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/211:37 amSJO - MDW
1 stop20h 16mMultiple Airlines
Tue 10/78:05 amMDW - SJO
2 stops28h 25mMultiple Airlines
Deal found 9/9$313
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 11/19:00 amSJO - MDW
1 stop11h 22mMultiple Airlines
Sat 11/86:30 amMDW - SJO
2 stops29h 44mMultiple Airlines
Deal found 9/9$315
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/1111:37 amSJO - MDW
1 stop23h 02mMultiple Airlines
Sat 10/1812:30 pmMDW - SJO
2 stops24h 00mMultiple Airlines
Deal found 9/9$317
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/221:23 pmSJO - MDW
1 stop7h 51mDelta
Sun 10/266:00 amMDW - SJO
1 stop6h 58mDelta
Deal found 9/11$326
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/111:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Thu 10/1610:30 amMDW - SJO
2 stops25h 11mMultiple Airlines
Deal found 9/9$334
This Southwest deal was found by Cheapflights users on 9/10. 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.
Fri 11/72:10 pmSJO - MDW
1 stop10h 00mSouthwest
Tue 11/115:05 amMDW - SJO
1 stop8h 10mSouthwest
Deal found 9/10$339
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1011:37 amSJO - MDW
1 stop26h 34mMultiple Airlines
Mon 10/134:24 pmMDW - SJO
2 stops16h 26mMultiple Airlines
Deal found 9/9$340
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Sun 11/166:00 amMDW - SJO
1 stop7h 06mDelta
Deal found 9/11$341
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 10/2712:35 pmSJO - MDW
2 stops22h 03mMultiple Airlines
Sun 11/210:12 amMDW - SJO
1 stop25h 12mMultiple Airlines
Deal found 9/9$353

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 September 11, 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

Sun 10/26

9:00 am-11:17 am

1 stop25h 17m

Chicago Midway

Sun 11/2

5:30 am-10:24 am

2 stops28h 54m

$317

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 12/4

7:00 am-6:00 pm

2 stops11h 00m

Chicago Midway

Mon 12/8

9:34 am-10:12 pm

2 stops12h 38m

$341

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/7

2:15 pm-10:14 pm

1 stop7h 59m

Chicago Midway

Sun 11/16

6:00 am-1:06 pm

1 stop7h 06m

$341

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Tue 9/30

6:15 am-12:45 pm

1 stop7h 30m

$377

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/2

1:30 pm-12:45 am

1 stop10h 15m

Chicago Midway

Tue 10/7

5:15 am-11:40 am

1 stop7h 25m

$396

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/16

12:55 pm-11:25 pm

1 stop9h 30m

Chicago Midway

Tue 10/21

5:15 am-11:40 am

1 stop7h 25m

$396

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 10/22

1:00 pm-11:35 pm

1 stop9h 35m

Chicago Midway

Sun 10/26

9:20 pm-12:35 pm

2 stops16h 15m

$401

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/30

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Tue 10/7

5:15 am-11:40 am

1 stop7h 25m

$408

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 11/1

12:35 pm-1:37 pm

2 stops24h 02m

$159

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/3

1:35 pm-12:41 pm

2 stops47h 06m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 18 results
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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 September 11, 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.

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.

  • How long is the flight from San José, San José Province to Chicago Midway Airport?

    There are many flights that can get you from San José, San José Province to Chicago Midway Airport in 8h 40m. Fly via Delta or Southwest to get the fastest option. The distance between San José, San José Province and Chicago Midway Airport is about 2206 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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
Chesterton

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