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$185+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$407
(Southwest)

One-way from

$185
(Southwest)

Popular in

June

Cheapest in

August

Average price

$967
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. 11% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($27 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 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 June 12, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/228:05 amMDW - SJO
2 stops11h 50mSouthwest
Sun 9/2812:35 pmSJO - MDW
1 stop7h 40mSouthwest
Deal found 6/11$407
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/319:12 pmMDW - SJO
1 stop14h 17mMultiple Airlines
Fri 8/88:50 amSJO - MDW
2 stops13h 27mMultiple Airlines
Deal found 6/11$454
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amMDW - SJO
1 stop6h 52mDelta
Sun 11/162:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 6/9$691

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 June 12, 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 9/22

8:05 am-6:55 pm

2 stops11h 50m

San José Juan Santamaria Intl

Sun 9/28

12:35 pm-9:15 pm

1 stop7h 40m

$407

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 7/31

9:12 pm-10:29 am

1 stop14h 17m

San José Juan Santamaria Intl

Fri 8/8

8:50 am-11:17 pm

2 stops13h 27m

$454

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/9

6:00 am-12:52 pm

1 stop6h 52m

San José Juan Santamaria Intl

Sun 11/16

2:17 pm-9:44 pm

1 stop7h 27m

$691

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 6/29

5:15 am-11:35 am

1 stop7h 20m

$185

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 7/5

9:12 pm-10:36 am

1 stop14h 24m

$232

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 11/17

1:00 pm-10:15 pm

2 stops9h 15m

$697

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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.

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

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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 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 $407 on this airline. An additional option worth looking into is Delta, starting at $691. Southwest is priced at 39% 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
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.
O'Hare Intl to San José flights
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Midway to Liberia flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$633FlexibilityNo cancel feeOn-time63%
DeltaCheapest$544Average$779FlexibilityNo cancel feeOn-timeN/A

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