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$151+ Cheap flights from Midway (MDW) to San José (SJO)

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to San José

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José (SJO). 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 August 14, 2025.

Round-trip from

$387
(Southwest)

One-way from

$151
(Orbitz)

Popular in

January

Cheapest in

August

Average price

$514
From Chicago Midway to San José Juan Santamaria Intl
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One-way flight from Chicago Midway to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 7% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midway to San José

Cheapest flights from Midway to San José
Explore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:15 amMDW - SJO
1 stop7h 19mFrontier
Sat 10/181:49 pmSJO - MDW
1 stop8h 36mFrontier
Deal found 8/12$367
This Southwest deal was found by Cheapflights users on 8/14. 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.
Tue 9/99:10 amMDW - SJO
1 stop10h 45mSouthwest
Wed 9/171:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 8/14$387
This Delta deal was found by Cheapflights users on 8/14. 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 11/66:00 amMDW - SJO
1 stop6h 50mDelta
Tue 11/112:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 8/14$394
This Delta deal was found by Cheapflights users on 8/14. 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 11/199:30 amMDW - SJO
2 stops12h 45mDelta
Tue 11/252:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 8/14$398
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 9/85:05 amMDW - SJO
1 stop8h 40mSouthwest
Sat 9/131:15 pmSJO - MDW
1 stop8h 30mSouthwest
Deal found 8/13$417
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1310:51 amMDW - SJO
1 stop24h 36mMultiple Airlines
Fri 9/192:55 pmSJO - MDW
2 stops17h 56mMultiple Airlines
Deal found 8/13$430
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 9/26:15 amMDW - SJO
1 stop7h 30mSouthwest
Tue 9/98:50 amSJO - MDW
1 stop8h 35mSouthwest
Deal found 8/13$432
This Delta deal was found by Cheapflights users on 8/13. 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 12/116:00 amMDW - SJO
1 stop16h 15mDelta
Tue 12/232:10 pmSJO - MDW
1 stop7h 55mDelta
Deal found 8/13$435
This Delta deal was found by Cheapflights users on 8/13. 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 12/111:05 pmMDW - SJO
1 stop9h 10mDelta
Wed 12/242:10 pmSJO - MDW
2 stops18h 42mDelta
Deal found 8/13$439

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San José 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Midway

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 10/11

6:15 am-12:34 pm

1 stop7h 19m

San José Juan Santamaria Intl

Sat 10/18

1:49 pm-11:25 pm

1 stop8h 36m

$367

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 9/10

6:25 am-6:55 pm

1 stop13h 30m

San José Juan Santamaria Intl

Tue 9/23

1:40 pm-11:20 pm

1 stop8h 40m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 11/11

10:15 am-8:30 pm

1 stop10h 15m

San José Juan Santamaria Intl

Tue 11/18

9:00 am-4:35 pm

1 stop7h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/9

9:10 am-6:55 pm

1 stop10h 45m

San José Juan Santamaria Intl

Tue 9/16

8:50 am-6:25 pm

1 stop8h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/9

9:10 am-6:55 pm

1 stop10h 45m

San José Juan Santamaria Intl

Wed 9/17

1:40 pm-11:20 pm

1 stop8h 40m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/8

5:05 am-12:45 pm

1 stop8h 40m

San José Juan Santamaria Intl

Thu 9/18

8:50 am-7:25 pm

1 stop9h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/8

5:05 am-12:45 pm

1 stop8h 40m

San José Juan Santamaria Intl

Wed 9/10

8:50 am-9:40 pm

1 stop11h 50m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 10/18

6:15 am-12:34 pm

1 stop7h 19m

$151

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/23

6:10 am-12:24 pm

1 stop7h 14m

$166

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 10/19

12:09 pm-10:42 am

1 stop23h 33m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 17 results
1
2

Best time to book a flight from Midway to San José

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

What is the cheapest month to book a flight from Chicago Midway Airport to San José, San José Province?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San José, San José Province (average of $398). Flying from Chicago Midway Airport to San José, San José Province in March is currently the most expensive (average of $555). 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.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated August 14, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to San José, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to San José. 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 into for flights to San José from Chicago Midway?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago Midway. Booking flights from Chicago Midway to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • What is the cheapest airline to fly from Chicago Midway Airport to San José, San José Province round-trip?

    Our cheapest airline available from Chicago Midway Airport to San José, San José Province is Southwest. Our recent data shows that you can find tickets from as low as $431 on this airline. Southwest is priced at 33% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San José, San José Province (average of $398). Flying from Chicago Midway Airport to San José, San José Province in March is currently the most expensive (average of $555). 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó

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Alternative routes for Midway to San José

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to San José

Discover the top airline that operate flights from Midway to San José. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$431Average$600FlexibilityNo cancel feeOn-time63%

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