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$167+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$397
(Kiwi.com)

One-way from

$167
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$455
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. 14% potential increase in price ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($45 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/17. 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 5/191:19 pmMDW - SJO
1 stop22h 08mMultiple Airlines
Fri 5/234:10 amSJO - MDW
2 stops15h 07mMultiple Airlines
Deal found 4/17$397
This Southwest deal was found by Cheapflights users on 4/16. 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.
Thu 8/145:05 amMDW - SJO
1 stop8h 40mSouthwest
Wed 8/201:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 4/16$437
This Delta deal was found by Cheapflights users on 4/16. 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.
Sun 8/316:00 amMDW - SJO
1 stop6h 48mDelta
Wed 10/221:13 pmSJO - MDW
1 stop7h 31mDelta
Deal found 4/16$446

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 April 17, 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

Mon 5/19

1:19 pm-10:27 am

1 stop22h 08m

San José Juan Santamaria Intl

Fri 5/23

4:10 am-8:17 pm

2 stops15h 07m

$397

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 5/12

7:50 am-7:40 pm

2 stops12h 50m

San José Juan Santamaria Intl

Wed 5/21

1:10 pm-10:50 pm

1 stop8h 40m

$482

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/26

6:04 am-11:55 am

1 stop6h 51m

San José Juan Santamaria Intl

Sat 5/3

1:20 pm-10:22 pm

1 stop8h 02m

$555

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/14

2:12 pm-11:33 am

2 stops22h 21m

$167

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 4/25

6:04 am-11:55 am

1 stop6h 51m

$205

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 4/23

1:25 pm-7:40 pm

1 stop7h 15m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-San José, San José Province flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 $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.

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

Find hourly flight availability from Midway to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Chicago Midway Airport to San José, San José Province, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in San José by month

Plan your trip to San José by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

Plan your trip to San José by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 2 different airlines.

  • What are the cheapest airlines flying 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 $482 on this airline. An additional option worth looking into is Delta, starting at $555. Southwest is priced at 31% 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Manuel Antonio
Heredia
Alajuela
Monteverde
Jacó

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Alternative routes for Midway to San José

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Top 2 airlines flying from Midway to San José

Discover the top 2 airlines 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$544Average$886FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$552Average$648FlexibilityNo cancel feeOn-time63%

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