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San Jose

$100+ Cheap flights from Midway (MDW) to San Jose, CA (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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This Southwest deal was found by Cheapflights users on 12/2. 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 12/305:45 amMDW - SJC
1 stop7h 30mSouthwest
Wed 1/73:00 pmSJC - MDW
1 stop5h 40mSouthwest
Deal found 12/2$379
This Delta deal was found by Cheapflights users on 12/3. 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 12/181:50 pmMDW - SJC
1 stop8h 46mDelta
Thu 1/810:45 pmSJC - MDW
1 stop9h 42mDelta
Deal found 12/3$397
This Delta deal was found by Cheapflights users on 12/3. 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 12/1812:45 pmMDW - SJC
1 stop10h 04mDelta
Wed 1/75:54 amSJC - MDW
2 stops10h 38mDelta
Deal found 12/3$402
This Southwest deal was found by Cheapflights users on 12/2. 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 12/305:45 amMDW - SJC
1 stop7h 30mSouthwest
Tue 1/62:55 pmSJC - MDW
1 stop5h 55mSouthwest
Deal found 12/2$409
This Southwest deal was found by Cheapflights users on 12/2. 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 12/305:45 amMDW - SJC
1 stop7h 30mSouthwest
Thu 1/87:05 amSJC - MDW
2 stops7h 30mSouthwest
Deal found 12/2$433
This Delta deal was found by Cheapflights users on 12/3. 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 12/1912:50 pmMDW - SJC
1 stop9h 51mDelta
Sun 1/115:05 pmSJC - MDW
2 stops13h 47mDelta
Deal found 12/3$453
This Southwest deal was found by Cheapflights users on 12/2. 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 12/168:45 amMDW - SJC
Nonstop4h 45mSouthwest
Mon 1/55:30 pmSJC - MDW
1 stop6h 00mSouthwest
Deal found 12/2$472
This Southwest deal was found by Cheapflights users on 12/3. 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 12/259:35 amMDW - SJC
1 stop7h 25mSouthwest
Mon 12/299:00 pmSJC - MDW
1 stop6h 15mSouthwest
Deal found 12/3$473
This Southwest deal was found by Cheapflights users on 12/3. 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 12/1912:55 pmMDW - SJC
1 stop6h 30mSouthwest
Sun 1/44:30 pmSJC - MDW
1 stop6h 40mSouthwest
Deal found 12/3$482

Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$267
(Southwest)

One-way from

$100
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$450

Good round-trip deal

$521 or less
Provider with most accurate pricing for Chicago Midway-San Jose flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San Jose flights.
Search Deals
From Chicago Midway to San Jose
Search Deals
One-way flight from Chicago Midway to San Jose
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Jose.
Search Deals

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 December 4, 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

Thu 3/5

6:00 am-12:36 pm

1 stop8h 36m

San Jose

Tue 3/10

10:45 pm-9:55 am

1 stop9h 10m

$268

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/5

9:50 am-5:38 pm

2 stops9h 48m

San Jose

Mon 3/9

10:45 pm-9:55 am

1 stop9h 10m

$276

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 1/9

6:45 am-12:56 pm

1 stop8h 11m

San Jose

Sun 1/11

8:05 pm-8:52 am

2 stops10h 47m

$293

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 3/4

6:00 am-12:30 pm

2 stops8h 30m

San Jose

Sun 3/22

10:55 pm-5:00 am

Nonstop4h 05m

$299

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 1/22

8:15 am-3:30 pm

1 stop9h 15m

San Jose

Sat 1/24

10:35 am-4:45 pm

Nonstop4h 10m

$299

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 3/6

1:28 pm-10:05 pm

2 stops10h 37m

San Jose

Mon 3/9

6:15 pm-8:50 am

2 stops12h 35m

$317

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 1/16

6:45 am-12:56 pm

1 stop8h 11m

San Jose

Mon 1/19

10:45 pm-9:53 am

1 stop9h 08m

$328

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 1/22

8:10 am-1:30 pm

1 stop7h 20m

San Jose

Sun 1/25

6:30 am-12:40 pm

Nonstop4h 10m

$343

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 1/7

8:10 am-2:45 pm

2 stops8h 35m

$106

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 3/11

2:03 pm-8:34 pm

1 stop8h 31m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to San Jose

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 Midway to San Jose in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Chicago Midway Airport-San Jose, California flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-San Jose, California flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Jose, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San Jose, California flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-San Jose, California 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 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, California?

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose, California (average of $145). Flying from Chicago Midway Airport to San Jose, California in November is currently the most expensive (average of $308). 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 December 4, 2025.

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

The best insider tips for Chicago Midway Airport to San Jose flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 4, 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
4,250 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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 0 inbound flights 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, California?

    There are many flights that can get you from Chicago Midway Airport to San Jose, California in 8h 30m. Fly via Delta or Southwest to get the fastest option. Chicago Midway Airport and San Jose, California are separated by a distance of 1832 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $333, Southwest will fly you from Chicago Midway Airport to San Jose, California and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. You may be able to fly from Chicago Midway Airport to San Jose, California for 26% less than the average price by searching for this airline.

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

    The cheapest flight price from Chicago Midway Airport to San Jose, California is $391. On average you can expect to pay $656. The most popular route, (Chicago Midway - San Jose), can usually be booked for $201.

  • 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, California?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose, California (average of $145). Flying from Chicago Midway Airport to San Jose, California in November is currently the most expensive (average of $308). 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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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$333Average$457FlexibilityNo cancel feeOn-time63%

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