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Midway

$153+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$294
(Kiwi.com)

One-way from

$153
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$547
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. 21% potential increase in price ($175 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Sun 12/76:37 pmMDW - SJO
1 stop17h 05mMultiple Airlines
Deal found 10/27$294
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 11/2111:24 amSJO - MDW
1 stop12h 05mMultiple Airlines
Mon 11/245:47 pmMDW - SJO
1 stop16h 32mMultiple Airlines
Deal found 10/27$323
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/52:31 pmSJO - MDW
1 stop9h 16mDelta
Tue 12/99:34 amMDW - SJO
2 stops12h 46mDelta
Deal found 10/28$339
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2712:39 pmSJO - MDW
1 stop8h 25mMultiple Airlines
Tue 12/306:14 amMDW - SJO
2 stops30h 11mMultiple Airlines
Deal found 10/26$351
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/2512:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Tue 12/306:14 amMDW - SJO
2 stops30h 11mMultiple Airlines
Deal found 10/27$362
This Southwest deal was found by Cheapflights users on 10/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:15 pmSJO - MDW
1 stop7h 55mSouthwest
Tue 11/117:00 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 10/26$366
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Sun 11/1612:47 pmMDW - SJO
1 stop9h 20mDelta
Deal found 10/28$368
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:45 amSJO - MDW
1 stop12h 37mMultiple Airlines
Sat 11/81:37 pmMDW - SJO
2 stops22h 48mMultiple Airlines
Deal found 10/26$370
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/2512:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Wed 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
Deal found 10/27$371
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Fri 1/23:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
Deal found 10/26$385
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:39 pmSJO - MDW
1 stop8h 25mMultiple Airlines
Thu 1/16:12 amMDW - SJO
2 stops21h 38mMultiple Airlines
Deal found 10/26$386

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 October 28, 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 12/5

7:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Tue 12/9

9:34 am-10:20 pm

2 stops12h 46m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/24

7:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 12/1

12:47 pm-10:07 pm

1 stop9h 20m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 11/23

2:31 pm-11:40 pm

1 stop9h 09m

Chicago Midway

Thu 11/27

9:34 am-10:07 pm

2 stops12h 33m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-4:31 pm

1 stop9h 31m

Chicago Midway

Sat 1/24

9:34 am-10:15 pm

2 stops12h 41m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/24

2:31 pm-10:26 pm

1 stop7h 55m

Chicago Midway

Wed 1/28

9:34 am-10:15 pm

2 stops12h 41m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-10:09 pm

1 stop15h 09m

Chicago Midway

Fri 1/23

10:53 am-10:15 pm

1 stop11h 22m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/7

2:15 pm-10:14 pm

1 stop7h 59m

Chicago Midway

Sun 11/16

12:47 pm-10:07 pm

1 stop9h 20m

$368

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/20

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Tue 1/20

12:48 pm-10:15 pm

1 stop9h 27m

$404

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 12/22

7:00 am-4:20 pm

1 stop9h 20m

Chicago Midway

Thu 1/22

10:53 am-10:15 pm

1 stop11h 22m

$404

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/10

1:19 pm-8:45 pm

2 stops31h 26m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 18 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust 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-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-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José-Chicago Midway Airport flights, Cheapflights users trust Priceline the most. Priceline 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-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

How often are flights from San José to Chicago delayed?

About 0% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.

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

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

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

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

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 October 28, 2025.
Read through reviews of airlines operating flights from San José to Chicago Midway Airport, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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. 1 airline 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.

  • How long is the flight from San José to Chicago Midway Airport?

    For as low as $339, Delta can have you in Chicago Midway Airport from San José in 9h 18m. The distance between San José and Chicago Midway Airport is about 2206 mi.

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

    Currently priced at $463, Southwest will fly you from San José to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. You may be able to fly from San José to Chicago Midway Airport for 26% less than the average price by searching for this airline.

  • 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.

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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for San José to Midway

See prices for flight routes from nearby airports that may be better suited for you.
San José to O'Hare Intl flights
Liberia to O'Hare Intl flights

Top airline flying from San José to Midway

Discover the top airline that operate flights from San José to Midway. 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$523FlexibilityNo cancel feeOn-time63%

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