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$149+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
May 17 — May 241
Sat 5/17
Sat 5/24
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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$257
(Trip.com)

One-way from

$149
(Mytrip)

Popular in

September

Cheapest in

November

Average price

$432

Good round-trip deal

$371 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Chicago Midway-San Jose flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San Jose flights.
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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. 7% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 12, 2025.

This Trip.com deal was found by Cheapflights users on 5/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/66:25 amMDW - SJC
1 stop9h 15mFrontier
Sun 6/82:30 pmSJC - MDW
1 stop22h 26mFrontier
Deal found 5/12$257
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/166:15 amMDW - SJC
1 stop14h 26mMultiple Airlines
Wed 5/286:00 amSJC - MDW
2 stops25h 00mMultiple Airlines
Deal found 5/10$331
This Delta deal was found by Cheapflights users on 5/11. 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.
Wed 7/29:24 amMDW - SJC
2 stops8h 43mDelta
Sun 8/3111:00 pmSJC - MDW
1 stop7h 40mDelta
Deal found 5/11$336
This Southwest deal was found by Cheapflights users on 5/10. 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 6/58:05 pmMDW - SJC
Nonstop4h 35mSouthwest
Thu 6/121:35 pmSJC - MDW
Nonstop4h 05mSouthwest
Deal found 5/10$383

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 May 12, 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

Fri 6/6

6:25 am-1:40 pm

1 stop9h 15m

San Jose

Sun 6/8

2:30 pm-2:56 pm

1 stop22h 26m

$257

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 7/2

4:26 pm-10:55 pm

1 stop8h 29m

San Jose

Sun 8/31

11:00 pm-8:40 am

1 stop7h 40m

$331

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 6/5

8:05 pm-10:40 pm

Nonstop4h 35m

San Jose

Thu 6/12

1:35 pm-7:40 pm

Nonstop4h 05m

$383

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 7/21

9:12 am-11:45 pm

2 stops40h 33m

$149

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 8/30

3:35 pm-6:05 pm

Nonstop4h 30m

$156

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 6/13

6:25 am-1:23 pm

1 stop8h 58m

$159

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 8/20

1:05 pm-7:50 pm

1 stop8h 45m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 Chicago Midway Airport-San Jose flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Jose flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Jose flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San Jose flights, Cheapflights users trust Expedia the most. Expedia 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 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?

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 $354). 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 May 12, 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 morning tend to be the most expensive. A flight at noon could potentially save you up to 14% on airfare.

Rainfall in San Jose by month

Plan your trip to San Jose by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Jose ranges from 0.0 - 3.1 inches per month. January is typically the wettest month, when rainfall can reach 3.1 in. July is typically the driest time to visit San Jose when rainfall is around 0.0 in.

Temperature in San Jose by month

Plan your trip to San Jose by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Jose, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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 May 12, 2025.
Read through reviews of airlines operating flights from Chicago to San Jose, such as Southwest, Delta and Frontier. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
6.0
Okay
3,288 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 2 inbound flights from Chicago Midway per day. 2 airlines have flights to San Jose from Chicago Midway on a regular basis.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Jose round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to San Jose round-trip from $257. Other airlines that can offer you cheap pricing are Delta, from $336, and Southwest, from $367. Frontier is priced at 41% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Jose one-way?

    One-way options have recently been found by users for as low as $156 on Southwest. Other airlines that offer cheap prices include Frontier from $159 and Delta from $160 one-way.

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

    The cheapest flight price from Chicago Midway Airport to San Jose is $175. On average you can expect to pay $329. The most popular route, (Chicago Midway - San Jose), can usually be booked for $257.

  • 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 $354). 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.

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Top 2 airlines flying from Midway to San Jose

Discover the top 2 airlines 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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$258FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$376Average$459FlexibilityNo cancel feeOn-time63%

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