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$228+ Cheap flights from San José (SJO) to Midway (MDW)

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from San José to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Midway (MDW). 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

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$394
(Kiwi.com)

One-way from

$228
(Kiwi.com)

Popular in

January

Cheapest in

March

Average price

$670
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago Midway flights.
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From San José Juan Santamaria Intl to Chicago Midway
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One-way flight from San José Juan Santamaria Intl to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($212 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 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 San José to Midway

Cheapest flights from San José to Midway
Explore the most affordable flight options available from San José to Midway. 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 4/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:52 amSJO - MDW
2 stops13h 25mMultiple Airlines
Sun 5/259:12 pmMDW - SJO
1 stop14h 15mMultiple Airlines
Deal found 4/16$394
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 8/141:40 pmSJO - MDW
1 stop9h 25mSouthwest
Tue 8/199:10 amMDW - SJO
1 stop10h 45mSouthwest
Deal found 4/16$436
This Booking.com deal was found by Cheapflights users on 4/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/281:47 pmSJO - MDW
1 stop23h 02mFrontier
Sat 7/56:20 amMDW - SJO
1 stop7h 11mFrontier
Deal found 4/15$476
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.
Mon 9/151:18 pmSJO - MDW
1 stop7h 26mDelta
Fri 9/196:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 4/16$478

Cheapflights Fare Finder

Customize your flight search to find flights from San José to Midway 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 San José to Chicago Midway Airport that are best for you.

Fly from

San José

Fly to

Midway

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/23

5:52 am-8:17 pm

2 stops13h 25m

Chicago Midway

Sun 5/25

9:12 pm-10:27 am

1 stop14h 15m

$394

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 6/28

1:47 pm-1:49 pm

1 stop23h 02m

Chicago Midway

Sat 7/5

6:20 am-12:31 pm

1 stop7h 11m

$476

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/23

1:10 pm-11:35 pm

1 stop9h 25m

Chicago Midway

Sun 5/25

9:55 am-7:40 pm

1 stop10h 45m

$484

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/3

1:20 pm-10:22 pm

1 stop8h 02m

Chicago Midway

Sat 5/10

6:00 am-11:59 am

1 stop6h 59m

$556

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/23

4:10 am-8:17 pm

2 stops15h 07m

$228

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 7/12

1:47 pm-1:49 pm

1 stop23h 02m

$283

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 7/12

8:45 am-8:25 pm

2 stops10h 40m

$287

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/23

1:20 pm-10:22 pm

1 stop8h 02m

$441

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/2

5:00 pm-5:59 pm

2 stops23h 59m

$3,058

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Compare providers for flights from San José to Midway

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 San José to Midway in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 San José, San José Province-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José, San José Province-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José, San José Province-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José, San José Province-Chicago Midway Airport 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 San José, San José Province-Chicago Midway Airport 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 San José to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José 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 San José to Chicago Midway Airport

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

Find hourly flight availability from San José to Midway. 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 San José, San José Province to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 32% versus a flight at noon.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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.
LATAM Airlines
7.5
Good
1,761 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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 San José to Midway. 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 from for flights from San José to Chicago Midway?

    San José Juan Santamaria Intl (SJO), located 8.8 mi from the city center, is the airport you fly out of when you book flights from San José to Chicago Midway. 0 airlines have flights from Juan Santamaria Intl to Chicago Midway on a regular basis. Booking flights from San José Juan Santamaria Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from San José, San José Province to Chicago Midway Airport round-trip?

    Currently priced at $476, Frontier will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $484 and $556, respectively. Users have found that Frontier is 34% cheaper than the other options available to this destination.

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

    $283 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $287 and $441, respectively.

  • Can I find deals for flights from San José to Midway that include hotel bookings?

    Yes. In addition to deals on San José to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Midway.

  • Can I find deals for business class flights from San José to Midway?

    Yes. Cheapflights offers flight deals from San José to Midway 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 San José, San José Province to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San José, San José Province to Chicago Midway Airport (average of $160). Flying from San José, San José Province to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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