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Midway

$161+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
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 enero 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mié. 3/113:05 pm
SJO
-
MDW
2 stops21h 36m
Multiple Airlines
mié. 3/1811:19 am
MDW
-
SJO
1 stop24h 23m
Multiple Airlines
Deal found 1/27$332
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
vie. 3/612:35 pm
SJO
-
MDW
1 stop8h 18m
Multiple Airlines
mar. 3/107:30 am
MDW
-
SJO
2 stops28h 08m
Multiple Airlines
Deal found 1/26$365
This Delta deal was found by Cheapflights users on 1/26. 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.
jue. 2/57:00 am
SJO
-
MDW
1 stop10h 29m
Delta
dom. 2/229:34 am
MDW
-
SJO
2 stops12h 28m
Delta
Deal found 1/26$367
This Southwest deal was found by Cheapflights users on 1/25. 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.
jue. 4/239:00 am
SJO
-
MDW
2 stops12h 45m
Southwest
dom. 4/266:50 am
MDW
-
SJO
1 stop7h 10m
Southwest
Deal found 1/25$384
This Delta deal was found by Cheapflights users on 1/26. 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.
mié. 2/42:31 pm
SJO
-
MDW
1 stop7h 51m
Delta
lun. 2/166:00 am
MDW
-
SJO
1 stop16h 02m
Delta
Deal found 1/26$394
This Southwest deal was found by Cheapflights users on 1/26. 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.
jue. 2/191:45 pm
SJO
-
MDW
1 stop8h 40m
Southwest
mié. 2/255:00 am
MDW
-
SJO
1 stop7h 50m
Southwest
Deal found 1/26$395
This Southwest deal was found by Cheapflights users on 1/25. 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.
vie. 5/11:10 pm
SJO
-
MDW
1 stop7h 45m
Southwest
mar. 5/56:00 am
MDW
-
SJO
1 stop7h 10m
Southwest
Deal found 1/25$396
This Southwest deal was found by Cheapflights users on 1/26. 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.
vie. 3/69:45 am
SJO
-
MDW
1 stop9h 20m
Southwest
mar. 3/106:00 am
MDW
-
SJO
1 stop7h 55m
Southwest
Deal found 1/26$406
This Southwest deal was found by Cheapflights users on 1/24. 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.
lun. 2/29:40 am
SJO
-
MDW
1 stop13h 15m
Southwest
dom. 2/226:05 am
MDW
-
SJO
1 stop6h 45m
Southwest
Deal found 1/24$412
This Southwest deal was found by Cheapflights users on 1/26. 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.
vie. 5/11:10 pm
SJO
-
MDW
1 stop7h 45m
Southwest
dom. 5/36:50 am
MDW
-
SJO
1 stop7h 10m
Southwest
Deal found 1/26$419

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 enero 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(Kiwi.com)

One-way from

$161
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$489
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. 4% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 enero 27, 2026.
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

jue. 4/23

9:00 am-10:45 pm

2 stops12h 45m

Chicago Midway

dom. 4/26

6:50 am-1:00 pm

1 stop7h 10m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

lun. 2/2

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

dom. 2/22

7:55 am-7:30 pm

2 stops11h 35m

$449

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mié. 3/11

8:45 am-7:20 pm

1 stop9h 35m

Chicago Midway

mié. 3/18

6:00 am-12:55 pm

1 stop7h 55m

$467

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mié. 2/25

9:40 am-8:15 pm

2 stops10h 35m

Chicago Midway

mar. 3/3

5:00 am-12:50 pm

1 stop7h 50m

$474

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jue. 2/19

2:25 pm-10:31 pm

1 stop8h 06m

Chicago Midway

mar. 2/24

9:34 am-10:02 pm

2 stops12h 28m

$486

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 2/13

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

mar. 2/17

10:49 am-10:02 pm

1 stop11h 13m

$486

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jue. 2/12

9:40 am-8:25 pm

1 stop10h 45m

Chicago Midway

dom. 2/15

10:30 am-7:30 pm

1 stop9h 00m

$490

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mié. 3/4

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

mar. 3/10

9:35 am-9:15 pm

2 stops12h 40m

$496

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 3/20

1:29 pm-3:25 pm

2 stops24h 56m

Chicago Midway

mar. 3/24

7:30 am-10:38 am

2 stops28h 08m

$504

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jue. 2/5

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

dom. 2/22

10:49 am-10:02 pm

1 stop11h 13m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 16 results
1
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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*
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 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 enero 27, 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
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

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 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 $384, Southwest can have you in Chicago Midway Airport from San José in 12h 45m. 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 19% 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
Lansing
Merrillville
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 enero 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$507FlexibilityNo cancel feeOn-time63%

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