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$43+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Feb 8 — Feb 151
Sat 2/8
Sat 2/15
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 February 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$150
(Trip.com)

One-way from

$43
(Trip.com)

Popular in

September

Cheapest in

July

Average price

$418

Good round-trip deal

$433 or less

Good one-way deal

$224 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. 12% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 3, 2025.

This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/36:40 amMDW - SJC
2 stops14h 32mFrontier
Mon 3/104:03 pmSJC - MDW
1 stop6h 14mFrontier
Deal found 2/2$150
This Kissandfly.com deal was found by Cheapflights users on 2/3. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/47:05 amMDW - SJC
3 stops17h 40mMultiple Airlines
Wed 3/59:03 amSJC - MDW
2 stops13h 14mMultiple Airlines
Deal found 2/3$279
This Southwest deal was found by Cheapflights users on 2/1. 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 3/39:45 amMDW - SJC
Nonstop4h 50mSouthwest
Mon 3/108:20 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 2/1$351
This Delta deal was found by Cheapflights users on 2/3. 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.
Tue 3/41:26 pmMDW - SJC
1 stop9h 44mDelta
Tue 3/116:15 amSJC - MDW
1 stop6h 00mDelta
Deal found 2/3$371

Find flights from Midway to San Jose within your budget

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 February 3, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 3/14

6:40 am-3:03 pm

1 stop10h 23m

San Jose

Mon 3/17

4:03 pm-12:17 am

1 stop6h 14m

$155

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 3/4

7:05 am-10:45 pm

3 stops17h 40m

San Jose

Wed 3/5

9:03 am-12:17 am

2 stops13h 14m

$279

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 5/15

6:25 pm-9:00 pm

Nonstop4h 35m

San Jose

Mon 5/19

8:55 pm-5:15 am

1 stop6h 20m

$361

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/13

1:16 pm-8:23 pm

1 stop9h 07m

San Jose

Tue 3/18

6:15 am-4:14 pm

1 stop7h 59m

$371

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 3/19

6:40 am-3:03 pm

1 stop10h 23m

$43

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 5/29

8:20 pm-9:46 am

2 stops15h 26m

$165

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 3/3

9:45 am-12:35 pm

Nonstop4h 50m

$176

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/27

1:16 pm-8:23 pm

1 stop9h 07m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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 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 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 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.

Travel insights for flights from Midway to San Jose

Get recent, data-driven insights about flights from Midway to San Jose including ideal travel times, pricing trends, and more.

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 $372). 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 February 3, 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 in the morning could potentially save you up to 37% on airfare.

Weekly flight availability from Chicago Midway Airport to San Jose

Explore weekly flight availability from Midway to San Jose. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 3, 2025.

The most flights from MDW to SJC are scheduled on a Thursday (4 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

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 February 3, 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
8.1
Very good
4,564 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,564 reviews
Southwest
8.1
Very good
4,564 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,415 reviews
Southwest
8.1
Very good
4,564 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Frontier
6.0
Okay
3,417 reviews
Southwest
8.1
Very good
4,564 reviews

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Overall

8.1

Food

7.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 $150. Other airlines that can offer you cheap pricing are Southwest, from $351, and Delta, from $371. Frontier is priced at 64% 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 $43 on Frontier. Other airlines that offer cheap prices include Southwest from $176 and Delta from $186 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 $184. On average you can expect to pay $341. The most popular route, (Chicago Midway - San Jose), can usually be booked for $197.

  • 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 $372). 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 February 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$174FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$376Average$463FlexibilityNo cancel feeOn-time63%
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