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$121+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Delta deal was found by Cheapflights users on 12/26. 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 12/319:50 amMDW - SJO
1 stop12h 05mDelta
Thu 2/127:00 amSJO - MDW
1 stop10h 45mDelta
Deal found 12/26$476
This Gurufare deal was found by Cheapflights users on 12/26. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - SJO
1 stop7h 30mFrontier
Wed 1/73:10 pmSJO - MDW
1 stop20h 21mFrontier
Deal found 12/26$512
This Delta deal was found by Cheapflights users on 12/27. 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 12/319:50 amMDW - SJO
1 stop12h 05mDelta
Thu 1/82:31 pmSJO - MDW
1 stop7h 36mDelta
Deal found 12/27$515
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 12/296:15 amMDW - SJO
1 stop9h 15mMultiple Airlines
Wed 12/314:30 pmSJO - MDW
2 stops20h 31mMultiple Airlines
Deal found 12/27$604
This Delta deal was found by Cheapflights users on 12/27. 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 12/289:29 amMDW - SJO
2 stops12h 26mDelta
Thu 1/17:00 amSJO - MDW
2 stops25h 49mDelta
Deal found 12/27$646
This Priceline deal was found by Cheapflights users on 12/27. 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.
Wed 12/316:12 amMDW - SJO
1 stop7h 30mFrontier
Fri 1/22:57 pmSJO - MDW
1 stop22h 24mFrontier
Deal found 12/27$656
This Delta deal was found by Cheapflights users on 12/26. 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 12/319:50 amMDW - SJO
1 stop12h 05mDelta
Tue 1/67:00 amSJO - MDW
1 stop15h 07mDelta
Deal found 12/26$691

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$346
(Kiwi.com)

One-way from

$121
(Cheapflightsfares)

Popular in

January

Cheapest in

November

Average price

$612
Provider with most accurate pricing for Chicago Midway-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San José Juan Santamaria Intl flights.
Search Deals
From Chicago Midway to San José Juan Santamaria Intl
Search Deals
One-way flight from Chicago Midway to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 28, 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

Wed 1/21

12:48 pm-10:15 pm

1 stop9h 27m

San José Juan Santamaria Intl

Fri 1/30

2:31 pm-10:22 pm

1 stop7h 51m

$358

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/3

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Tue 2/10

9:40 am-10:55 pm

1 stop13h 15m

$359

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/3

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

Tue 2/10

7:00 am-5:29 pm

1 stop10h 29m

$384

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/2

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

Mon 2/23

7:00 am-8:54 am

2 stops25h 54m

$389

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/26

1:28 pm-10:02 pm

2 stops8h 34m

San José Juan Santamaria Intl

Tue 3/3

2:25 pm-10:33 pm

1 stop8h 08m

$415

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/27

9:34 am-10:02 pm

2 stops12h 28m

San José Juan Santamaria Intl

Tue 3/3

2:25 pm-10:33 pm

1 stop8h 08m

$415

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/2

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

Mon 2/9

7:00 am-5:29 pm

1 stop10h 29m

$428

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 2/7

1:00 pm-7:30 pm

1 stop6h 30m

San José Juan Santamaria Intl

Sat 2/14

9:30 am-5:25 pm

1 stop7h 55m

$448

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/4

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Sun 2/8

9:40 am-10:55 pm

1 stop13h 15m

$450

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 1/12

6:10 am-1:36 pm

1 stop7h 26m

$121

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 18 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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 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 flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-San José flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José flights, Cheapflights users trust eDreams the most. eDreams 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 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

How often are flights from Chicago to San José delayed?

About 100% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 97 minutes.

What is the most punctual flight time for Chicago to San José flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

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 December 28, 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
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    Delta and Southwest can get you from Chicago Midway Airport to San José in just under 9h 27m. Your travel time can differ by up to 3h 48m. The distance from Chicago Midway Airport to San José is about 2206 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Southwest is currently your cheapest option to San José, with prices starting at $394. Users have found that Southwest is 34% cheaper than the other options available to this destination.

  • 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.

See more FAQs

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

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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 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$394Average$572FlexibilityNo cancel feeOn-time63%

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