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$202+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
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 January 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(Kiwi.com)

One-way from

$202
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$706
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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High demand for flights, 27% potential price rise
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Best time to find cheap flights, 11% potential price drop
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Average for round-trip flights in January 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 January 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Tue 2/2512:29 pmSJO - MDW
2 stops18h 38mMultiple Airlines
Sat 3/112:43 pmMDW - SJO
1 stop22h 41mMultiple Airlines
Deal found 1/16$357
This Southwest deal was found by Cheapflights users on 1/14. 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 3/111:55 pmSJO - MDW
1 stop8h 45mSouthwest
Tue 4/85:55 amMDW - SJO
1 stop7h 15mSouthwest
Deal found 1/14$544
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/241:42 pmSJO - MDW
1 stop9h 13mFrontier
Fri 5/306:44 pmMDW - SJO
1 stop18h 38mFrontier
Deal found 1/15$551
This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:13 pmSJO - MDW
1 stop7h 34mDelta
Tue 10/286:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 1/15$651

Find flights from San José to Midway within your budget

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/25

12:29 pm-7:07 am

2 stops18h 38m

Chicago Midway

Sat 3/1

12:43 pm-11:24 am

1 stop22h 41m

$357

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/11

1:55 pm-11:40 pm

1 stop8h 45m

Chicago Midway

Tue 4/8

5:55 am-12:10 pm

1 stop7h 15m

$544

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/24

1:42 pm-11:55 pm

1 stop9h 13m

Chicago Midway

Fri 5/30

6:44 pm-12:22 pm

1 stop18h 38m

$551

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 2/3

7:00 am-6:11 pm

2 stops11h 11m

Chicago Midway

Mon 2/17

10:57 am-10:12 pm

1 stop11h 15m

$651

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/26

12:29 pm-7:29 pm

1 stop31h 00m

$202

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/15

12:55 pm-10:04 pm

1 stop9h 09m

$221

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/16

1:10 pm-10:50 pm

1 stop8h 40m

$299

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/11

7:00 am-4:20 pm

1 stop9h 20m

$352

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/24

12:27 pm-4:54 pm

2 stops27h 27m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 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 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.

Travel insights for flights from San José to Midway

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

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 January 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 January 17, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from San José to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

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
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

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
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

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 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 $544, Southwest will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $551 and $651, respectively. Users have found that Southwest is 32% 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?

    $221 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 $299 and $352, 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
New Buffalo
Hammond
Benton Harbor
Porter
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Valparaiso
Chesterton

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