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Midway

$249+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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Cheap 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 May 19, 2026.

This Southwest deal was found by Cheapflights users on 5/14. 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 10/61:00 pm
SJO
-
MDW
1 stop9h 00m
Southwest
Mon 10/128:40 pm
MDW
-
SJO
2 stops16h 00m
Southwest
Deal found 5/14$453
This Delta deal was found by Cheapflights users on 5/18. 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 11/62:23 pm
SJO
-
MDW
1 stop7h 22m
Delta
Mon 11/96:00 am
MDW
-
SJO
1 stop7h 05m
Delta
Deal found 5/18$476
This Delta deal was found by Cheapflights users on 5/15. 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.
Sat 11/147:00 am
SJO
-
MDW
1 stop14h 45m
Delta
Sat 11/2810:35 am
MDW
-
SJO
1 stop11h 40m
Delta
Deal found 5/15$487
This Southwest deal was found by Cheapflights users on 5/17. 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 5/289:00 am
SJO
-
MDW
2 stops10h 15m
Southwest
Tue 6/912:00 pm
MDW
-
SJO
1 stop8h 40m
Southwest
Deal found 5/17$493
This Southwest deal was found by Cheapflights users on 5/14. 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.
Wed 9/99:00 am
SJO
-
MDW
1 stop7h 40m
Southwest
Mon 9/1410:05 am
MDW
-
SJO
2 stops9h 35m
Southwest
Deal found 5/14$500
This Southwest deal was found by Cheapflights users on 5/16. 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 10/229:00 am
SJO
-
MDW
2 stops10h 15m
Southwest
Wed 10/286:05 am
MDW
-
SJO
1 stop7h 00m
Southwest
Deal found 5/16$503
This Southwest deal was found by Cheapflights users on 5/18. 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 9/19:00 am
SJO
-
MDW
1 stop7h 40m
Southwest
Sun 9/68:40 am
MDW
-
SJO
2 stops11h 00m
Southwest
Deal found 5/18$504
This Delta deal was found by Cheapflights users on 5/18. 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.
Tue 8/251:14 pm
SJO
-
MDW
1 stop8h 22m
Delta
Mon 8/316:00 am
MDW
-
SJO
1 stop6h 56m
Delta
Deal found 5/18$511
This Southwest deal was found by Cheapflights users on 5/18. 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 11/59:00 am
SJO
-
MDW
2 stops11h 20m
Southwest
Mon 11/98:40 pm
MDW
-
SJO
2 stops15h 40m
Southwest
Deal found 5/18$519
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:14 pm
SJO
-
MDW
1 stop8h 22m
Delta
Sun 8/306:05 am
MDW
-
SJO
1 stop6h 44m
Delta
Deal found 5/14$521

Find 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 May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$493
(Southwest)

One-way from

$291
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$835
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago Midway flights.
Search Deals
From San José Juan Santamaria Intl to Chicago Midway
Search Deals
One-way flight from San José Juan Santamaria Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 19, 2026.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 8/25

1:14 pm-10:36 pm

1 stop8h 22m

Chicago Midway

Sun 8/30

6:05 am-11:49 am

1 stop6h 44m

$521

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/24

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Sat 9/26

10:25 am-6:00 pm

1 stop8h 35m

$528

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 9/12

1:15 pm-10:00 pm

1 stop7h 45m

Chicago Midway

Tue 9/15

10:10 am-6:40 pm

2 stops9h 30m

$539

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/18

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Fri 9/25

10:05 am-6:40 pm

2 stops9h 35m

$565

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 8/21

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Tue 9/1

10:10 am-6:40 pm

2 stops9h 30m

$565

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 10/21

1:00 pm-11:00 pm

1 stop9h 00m

Chicago Midway

Sun 10/25

6:55 am-12:40 pm

1 stop6h 45m

$573

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/27

9:00 am-7:30 pm

2 stops9h 30m

Chicago Midway

Fri 9/4

9:20 am-6:40 pm

2 stops10h 20m

$579
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/10

1:25 pm-9:46 pm

1 stop7h 21m

Chicago Midway

Thu 9/17

6:00 am-11:54 am

1 stop6h 54m

$584

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 8/24

9:00 am-6:00 pm

1 stop8h 00m

Chicago Midway

Sun 8/30

10:15 am-6:40 pm

2 stops9h 25m

$605

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 10/18

1:05 pm-12:55 am

1 stop10h 50m

Chicago Midway

Sun 10/25

9:55 pm-12:35 pm

2 stops15h 40m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 20 resultsSorted by cheapest first
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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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-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 much does it cost to fly round-trip from San José to Chicago Midway Airport?

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 May 19, 2026.
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
7.9
Good
4,284 reviews

Crew

8.6

Overall

7.9

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Overall

7.9

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $528, Delta can have you in Chicago Midway Airport from San José in 11h 30m. The distance between San José and Chicago Midway Airport 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 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 17% 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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

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 May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$507FlexibilityNo cancel feeOn-time63%

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