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$163+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(CheapOair)

One-way from

$164
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$838
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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High demand for flights, 11% potential price rise
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Best time to find cheap flights, 5% potential price drop
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Average for round-trip flights in January 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 January 21, 2025.

This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/216:48 pmMDW - SJO
1 stop16h 43mFrontier
Sat 3/112:55 pmSJO - MDW
1 stop9h 09mFrontier
Deal found 1/20$354
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/1012:49 pmMDW - SJO
1 stop22h 30mMultiple Airlines
Mon 3/1711:24 amSJO - MDW
2 stops11h 34mMultiple Airlines
Deal found 1/19$369
This Southwest deal was found by Cheapflights users on 1/20. 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 4/291:25 pmMDW - SJO
1 stop7h 15mSouthwest
Tue 5/61:10 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 1/20$539
This Delta deal was found by Cheapflights users on 1/20. 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
Thu 11/277:00 amSJO - MDW
1 stop7h 56mDelta
Deal found 1/20$542

Find flights from Midway to San José within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/21

6:48 pm-11:31 am

1 stop16h 43m

San José Juan Santamaria Intl

Sat 3/1

12:55 pm-10:04 pm

1 stop9h 09m

$354

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 3/10

12:49 pm-10:19 am

1 stop22h 30m

San José Juan Santamaria Intl

Mon 3/17

11:24 am-11:58 pm

2 stops11h 34m

$369

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 4/29

1:25 pm-7:40 pm

1 stop7h 15m

San José Juan Santamaria Intl

Tue 5/6

1:10 pm-10:50 pm

1 stop8h 40m

$539

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 3/11

12:51 pm-5:47 am

2 stops17h 56m

San José Juan Santamaria Intl

Tue 3/18

7:00 am-6:02 pm

2 stops10h 02m

$652

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 5/16

3:49 pm-11:33 am

2 stops20h 44m

$163

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 5/5

5:50 am-12:10 pm

1 stop7h 20m

$250

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 3/25

9:25 am-9:24 pm

2 stops12h 59m

$305

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 7/11

6:44 pm-12:22 pm

1 stop18h 38m

$474

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 6/14

6:00 am-11:48 am

1 stop6h 48m

$856

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
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.

Travel insights for flights from Midway to San José

Get recent, data-driven insights about flights from Midway to San José including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Volaris
6.7
Okay
1,249 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,440 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier. Our recent data shows that you can find tickets from as low as $354 on this airline. Additional options worth looking into are Southwest and Delta, starting at $560 and $648 round-trip. Frontier is priced at 55% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San José, San José Province one-way?

    $265 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Volaris, with prices starting from $305 and $476, respectively.

  • 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
Jacó
Monteverde
Alajuela

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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
O'Hare Intl to Liberia flights
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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$648FlexibilityNo cancel feeOn-time63%
DeltaCheapest$584Average$831FlexibilityNo cancel feeOn-timeN/A
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