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$131+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(Kiwi.com)

One-way from

$131
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$477
Provider with most accurate pricing for Chicago Midway-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San José Juan Santamaria Intl flights.
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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. 8% potential increase in price ($56 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 September 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 September 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/239:26 pmMDW - SJO
2 stops39h 04mMultiple Airlines
Thu 10/3011:37 amSJO - MDW
1 stop19h 55mMultiple Airlines
Deal found 9/25$312
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Tue 10/218:05 amMDW - SJO
2 stops28h 25mMultiple Airlines
Sat 10/251:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Deal found 9/24$315
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Wed 10/88:05 amMDW - SJO
2 stops28h 25mMultiple Airlines
Sat 10/111:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Deal found 9/24$321
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Tue 10/75:56 pmMDW - SJO
2 stops18h 34mMultiple Airlines
Sat 10/111:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Deal found 9/24$322
This Southwest deal was found by Cheapflights users on 9/24. 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 10/285:15 amMDW - SJO
1 stop7h 35mSouthwest
Sat 11/11:10 pmSJO - MDW
1 stop8h 20mSouthwest
Deal found 9/24$340
This Delta deal was found by Cheapflights users on 9/24. 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.
Sat 11/2910:47 amMDW - SJO
1 stop11h 20mDelta
Tue 12/97:00 amSJO - MDW
2 stops11h 00mDelta
Deal found 9/24$344
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/245:28 pmMDW - SJO
1 stop18h 13mMultiple Airlines
Tue 10/2812:35 pmSJO - MDW
2 stops23h 06mMultiple Airlines
Deal found 9/24$345
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 11/12:05 pmMDW - SJO
1 stop11h 45mMultiple Airlines
Sat 11/89:00 amSJO - MDW
1 stop12h 22mMultiple Airlines
Deal found 9/24$346
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/175:28 pmMDW - SJO
1 stop18h 13mMultiple Airlines
Mon 10/2012:35 pmSJO - MDW
2 stops33h 50mMultiple Airlines
Deal found 9/24$357
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 12/42:15 pmMDW - SJO
1 stop21h 12mMultiple Airlines
Tue 12/91:19 pmSJO - MDW
2 stops32h 13mMultiple Airlines
Deal found 9/25$359
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/1611:49 amMDW - SJO
1 stop23h 52mMultiple Airlines
Sun 10/195:25 pmSJO - MDW
2 stops15h 08mMultiple Airlines
Deal found 9/24$367

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 September 25, 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

Sun 10/19

6:25 am-12:05 pm

1 stop6h 40m

San José Juan Santamaria Intl

Wed 10/22

1:00 pm-11:35 pm

1 stop9h 35m

$381

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 10/29

5:25 am-12:05 pm

1 stop7h 40m

San José Juan Santamaria Intl

Wed 11/5

2:15 pm-10:10 pm

1 stop7h 55m

$381

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 11/29

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

Sat 12/6

2:31 pm-11:32 pm

1 stop9h 01m

$408

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 10/19

6:45 am-12:40 pm

1 stop6h 55m

San José Juan Santamaria Intl

Thu 10/23

12:55 pm-11:25 pm

1 stop9h 30m

$421

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/5

5:55 am-7:30 pm

1 stop13h 35m

San José Juan Santamaria Intl

Thu 2/26

1:50 pm-10:15 pm

1 stop8h 25m

$423

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 10/18

5:05 am-12:00 pm

1 stop7h 55m

San José Juan Santamaria Intl

Wed 10/22

1:00 pm-8:20 am

2 stops18h 20m

$425

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 12/4

10:15 am-8:30 pm

1 stop10h 15m

San José Juan Santamaria Intl

Tue 12/9

9:00 am-4:35 pm

1 stop7h 35m

$436

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/21

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Tue 1/27

7:00 am-4:25 pm

1 stop9h 25m

$467

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 11/19

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

Tue 11/25

7:00 am-4:38 pm

1 stop9h 38m

$486

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 10/7

5:56 pm-11:30 am

2 stops18h 34m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to San José

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San José in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San José, San José Province flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José, San José Province flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José, San José Province flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José, San José Province flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San José, San José Province flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $553). 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 September 25, 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
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

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

    Departing from Chicago Midway Airport to San José, San José Province will take you 6h 40m. The distance from Chicago Midway Airport to San José, San José Province is about 2206 mi. This flight may include one or multiple stops.

  • 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 $394 on this airline. Southwest is priced at 38% 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 $553). 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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$394Average$613FlexibilityNo cancel feeOn-time63%

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