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$96+ Cheap flights from Midway (MDW) to San Jose (SJC)

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to San Jose

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Jose (SJC). 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 September 16, 2025.

Round-trip from

$265
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$462

Good round-trip deal

$343 or less

Good one-way deal

$155 or less
From Chicago Midway to San Jose
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One-way flight from Chicago Midway to San Jose
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Highest demand for flights based on searches. 14% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to San Jose.
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Price to beat on a one-way flight from Chicago Midway to San Jose.
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Find flight deals from Midway to San Jose

Cheapest flights from Midway to San Jose
Explore the most affordable flight options available from Midway to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Mon 10/66:45 pmSJC - MDW
2 stops16h 53mMultiple Airlines
Deal found 9/15$265
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Fri 10/1012:35 pmSJC - MDW
1 stop9h 49mMultiple Airlines
Deal found 9/14$335
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/141:08 pmMDW - SJC
2 stops21h 10mDelta
Sat 10/186:20 amSJC - MDW
1 stop9h 23mDelta
Deal found 9/15$356
This Southwest deal was found by Cheapflights users on 9/16. 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.
Tue 10/215:25 pmMDW - SJC
Nonstop4h 30mSouthwest
Wed 10/227:30 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 9/16$359
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:05 amMDW - SJC
1 stop6h 15mSouthwest
Wed 10/297:30 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 9/15$365
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/141:08 pmMDW - SJC
2 stops21h 10mDelta
Fri 10/1710:25 pmSJC - MDW
1 stop9h 15mDelta
Deal found 9/15$366
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:15 amMDW - SJC
1 stop7h 25mSouthwest
Wed 12/316:30 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 9/15$369
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:26 pmMDW - SJC
2 stops16h 06mFrontier
Mon 10/2012:35 pmSJC - MDW
1 stop9h 49mFrontier
Deal found 9/14$373
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/245:05 amMDW - SJC
1 stop6h 15mSouthwest
Wed 10/297:30 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 9/14$375

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Jose 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Jose that are best for you.

Fly from

Midway

Fly to

San Jose

Route

Depart

Return

Price

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 2/24

5:25 pm-1:01 pm

2 stops21h 36m

San Jose

Wed 2/25

10:30 pm-9:56 am

1 stop9h 26m

$356

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 2/27

8:00 am-10:50 am

Nonstop4h 50m

San Jose

Mon 3/2

6:30 am-12:40 pm

Nonstop4h 10m

$369

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 10/24

5:05 am-9:20 am

1 stop6h 15m

San Jose

Wed 10/29

7:30 am-1:35 pm

Nonstop4h 05m

$375

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/8

6:05 am-11:20 am

1 stop7h 15m

San Jose

Tue 10/14

6:30 am-3:15 pm

1 stop6h 45m

$379

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 12/25

5:15 am-12:10 pm

1 stop8h 55m

San Jose

Thu 1/1

2:40 pm-11:40 pm

1 stop7h 00m

$379

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 12/25

9:35 am-3:00 pm

1 stop7h 25m

San Jose

Wed 12/31

8:40 am-5:10 pm

1 stop6h 30m

$379

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/22

11:55 am-4:30 pm

1 stop6h 35m

San Jose

Wed 10/22

6:50 pm-5:00 am

1 stop8h 10m

$379

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 2/12

8:00 am-10:50 am

Nonstop4h 50m

$180

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 10/25

4:10 pm-6:40 pm

Nonstop4h 30m

$180

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/22

5:25 pm-7:55 pm

Nonstop4h 30m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 17 results
1
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The best insider tips for Chicago Midway Airport to San Jose flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Jose trip
Airports
MDW

Use the Orange Line train for a quick, cost-effective way to reach MDW, taking less than 30 minutes from downtown Chicago.

Read more about MDWby Ramsey Qubein
SJC

For quick access to San Francisco, use the Airport Flyer bus to connect to BART at Milpitas station.

Read more about SJCby Daniel Scheffler
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on SJC

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more

Best time to book a flight from Midway to San Jose

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

What is the cheapest month to book a flight from Chicago Midway Airport to San Jose?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose (average of $255). Flying from Chicago Midway Airport to San Jose in June is currently the most expensive (average of $358). 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.

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

Find hourly flight availability from Midway to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to San Jose is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 13% on airfare.

Reviews of airlines servicing San Jose

Get insights into the airlines that provide service to San Jose. 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 San Jose. Reviews last updated September 16, 2025.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to San Jose. 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 into for flights to San Jose from Chicago Midway?

    For a flight from Chicago Midway to San Jose, you will be flying into San Jose. San Jose (SJC) is just 2.9 mi from the center of the city. San Jose is the only San Jose airport and it handles 1 inbound flight from Chicago Midway per day. 1 airline has flights to San Jose from Chicago Midway on a regular basis.

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

    A quick flight from Chicago Midway Airport to San Jose can take about 9h 06m. Delta provides one of the quickest options available for as low as $356. The distance from Chicago Midway Airport to San Jose is about 1832 mi.

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

    Cheapflights users have booked flights from Chicago Midway Airport to San Jose round-trip from $333. Southwest is priced at 28% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Chicago Midway Airport to San Jose?

    The cheapest flight price from Chicago Midway Airport to San Jose is $86. On average you can expect to pay $363. The most popular route, (Chicago Midway - San Jose), can usually be booked for $249.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to San Jose 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 Chicago Midway Airport to San Jose?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose (average of $255). Flying from Chicago Midway Airport to San Jose in June is currently the most expensive (average of $358). 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

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Alternative routes for Midway to San Jose

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Top airline flying from Midway to San Jose

Discover the top airline that operate flights from Midway to San Jose. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$333Average$460FlexibilityNo cancel feeOn-time63%

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