HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
dic. 4 — dic. 111
jue. 12/4
jue. 12/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to San Jose with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 noviembre 4, 2025.

This Delta deal was found by Cheapflights users on 11/3. 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.
mar. 12/910:49 amMDW - SJC
2 stops13h 23mDelta
vie. 12/127:45 pmSJC - MDW
2 stops11h 34mDelta
Deal found 11/3$314
This Delta deal was found by Cheapflights users on 11/3. 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.
jue. 12/119:59 amMDW - SJC
2 stops14h 13mDelta
mar. 1/205:00 pmSJC - MDW
2 stops14h 08mDelta
Deal found 11/3$324
This Delta deal was found by Cheapflights users on 11/4. 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. 12/312:50 pmMDW - SJC
1 stop9h 51mDelta
sáb. 12/67:45 pmSJC - MDW
2 stops11h 34mDelta
Deal found 11/4$350
This Delta deal was found by Cheapflights users on 11/3. 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.
lun. 12/81:50 pmMDW - SJC
1 stop8h 46mDelta
vie. 12/127:45 pmSJC - MDW
2 stops11h 34mDelta
Deal found 11/3$360
This Delta deal was found by Cheapflights users on 11/3. 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.
lun. 12/81:14 pmMDW - SJC
2 stops12h 39mDelta
sáb. 12/137:45 pmSJC - MDW
2 stops11h 34mDelta
Deal found 11/3$365
This Southwest deal was found by Cheapflights users on 11/3. 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.
dom. 12/77:50 amMDW - SJC
Nonstop4h 45mSouthwest
mar. 12/166:30 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 11/3$377
This Southwest deal was found by Cheapflights users on 11/3. 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.
mié. 12/31:55 pmMDW - SJC
2 stops7h 55mSouthwest
mié. 12/106:30 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 11/3$382
This Delta deal was found by Cheapflights users on 11/3. 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.
dom. 12/712:50 pmMDW - SJC
1 stop9h 51mDelta
mar. 12/166:59 pmSJC - MDW
2 stops12h 20mDelta
Deal found 11/3$400

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 noviembre 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Delta)

One-way from

$100
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$689

Good round-trip deal

$521 or less

Good one-way deal

$189 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. 15% potential increase in price ($82 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 November 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Jose.
Search Deals
Price to beat on a one-way 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 noviembre 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

mar. 12/9

10:49 am-10:12 pm

2 stops13h 23m

San Jose

vie. 12/12

7:45 pm-9:19 am

2 stops11h 34m

$314

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

mar. 12/16

1:14 pm-10:12 pm

2 stops10h 58m

San Jose

mié. 12/17

6:35 am-4:34 pm

1 stop7h 59m

$350

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/11

9:59 am-10:12 pm

2 stops14h 13m

San Jose

mié. 1/14

7:00 am-10:09 pm

2 stops13h 09m

$355

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/11

9:34 am-6:56 pm

2 stops11h 22m

San Jose

sáb. 1/17

6:15 am-4:16 pm

1 stop8h 01m

$360

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

lun. 12/8

1:50 pm-8:36 pm

1 stop8h 46m

San Jose

vie. 12/12

7:45 pm-9:19 am

2 stops11h 34m

$360

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

mar. 2/24

1:49 pm-8:53 pm

1 stop9h 04m

San Jose

mié. 2/25

1:26 pm-12:01 pm

2 stops20h 35m

$374

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

lun. 12/8

8:45 am-11:30 am

Nonstop4h 45m

San Jose

dom. 12/14

6:30 am-12:40 pm

Nonstop4h 10m

$387

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

dom. 12/7

7:50 am-10:35 am

Nonstop4h 45m

San Jose

mar. 12/16

6:35 am-3:00 pm

1 stop6h 25m

$387

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

vie. 1/16

8:05 am-10:55 am

Nonstop4h 50m

San Jose

lun. 1/19

6:30 am-12:40 pm

Nonstop4h 10m

$387

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

mié. 2/25

6:00 am-12:30 pm

2 stops8h 30m

San Jose

vie. 2/27

12:25 pm-6:30 pm

Nonstop4h 05m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 21 results
1
2
3

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 November.
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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose, California (average of $169). Flying from Chicago Midway Airport to San Jose, California in November is currently the most expensive (average of $252). 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 noviembre 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

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

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 noviembre 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
4,239 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

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 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 13h 23m. Fly via Delta to get the fastest option. Chicago Midway Airport and San Jose, California are separated by a distance of 1832 mi.

  • 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 27% 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 $179. On average you can expect to pay $496. The most popular route, (Chicago Midway - San Jose), can usually be booked for $314.

  • 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to San Jose, California (average of $169). Flying from Chicago Midway Airport to San Jose, California in November is currently the most expensive (average of $252). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to San Jose

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Ontario flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
Midway to Las Vegas flights
Midway to Los Angeles flights
O'Hare Intl to Palm Springs flights
Midway to San Francisco flights
O'Hare Intl to Burbank flights
O'Hare Intl to San Jose flights
O'Hare Intl to Sacramento flights
O'Hare Intl to Reno flights
Rockford to Las Vegas flights
Midway to San Diego flights
Midway to Ontario flights
Midway to Santa Ana flights
O'Hare Intl to Oakland flights
Midway to Palm Springs flights
Midway to Burbank flights
O'Hare Intl to Long Beach flights
O'Hare Intl to Santa Barbara flights
Midway to Sacramento flights
Midway to Long Beach flights
Midway to Oakland flights
Midway to Reno flights
O'Hare Intl to Fresno flights
O'Hare Intl to San Luis Obispo flights
O'Hare Intl to Medford flights
O'Hare Intl to Monterey flights
Midway to Medford flights
O'Hare Intl to Santa Rosa flights
Midway to Fresno flights
O'Hare Intl to Bakersfield flights
O'Hare Intl to Tijuana flights
O'Hare Intl to Yuma flights
O'Hare Intl to Arcata flights
O'Hare Intl to Redding flights
O'Hare Intl to Mexicali flights
Midway to Mexicali flights
Midway to Tijuana flights
O'Hare Intl to Mammoth Lakes flights
O'Hare Intl to Merced flights

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 noviembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$333Average$458FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.