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$100+ Cheap flights from San Jose, CA (SJC) to Midway (MDW)

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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap flight deals from San Jose to Midway

Cheapest flights from San Jose to Midway
Explore the most affordable flight options available from San Jose to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 7, 2025.

This Southwest deal was found by Cheapflights users on 12/7. 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.
Wed 12/318:55 amSJC - MDW
1 stop6h 00mSouthwest
Mon 1/511:15 amMDW - SJC
1 stop7h 45mSouthwest
Deal found 12/7$447
This Southwest deal was found by Cheapflights users on 12/6. 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 12/308:00 amSJC - MDW
Nonstop4h 05mSouthwest
Sun 1/45:15 amMDW - SJC
1 stop6h 25mSouthwest
Deal found 12/6$472
This Southwest deal was found by Cheapflights users on 12/6. 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 12/308:00 amSJC - MDW
Nonstop4h 05mSouthwest
Sat 1/311:20 amMDW - SJC
1 stop6h 10mSouthwest
Deal found 12/6$481
This Delta deal was found by Cheapflights users on 12/6. 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.
Sat 12/2012:31 pmSJC - MDW
1 stop7h 51mDelta
Fri 1/91:49 pmMDW - SJC
1 stop9h 39mDelta
Deal found 12/6$482
This Southwest deal was found by Cheapflights users on 12/5. 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.
Sat 12/278:55 pmSJC - MDW
1 stop6h 20mSouthwest
Fri 1/25:00 amMDW - SJC
2 stops7h 50mSouthwest
Deal found 12/5$504
This Southwest deal was found by Cheapflights users on 12/5. 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.
Sat 12/276:35 amSJC - MDW
1 stop8h 10mSouthwest
Thu 1/18:20 amMDW - SJC
1 stop7h 45mSouthwest
Deal found 12/5$517

Find flight deals from San Jose to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Midway (MDW). 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 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$366
(Southwest)

One-way from

$100
(Kiwi.com)

Popular in

September

Cheapest in

February

Average price

$481

Good round-trip deal

$467 or less

Good one-way deal

$131 or less
Provider with most accurate pricing for San Jose-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-Chicago Midway flights.
Search Deals
From San Jose to Chicago Midway
Search Deals
One-way flight from San Jose to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 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 San Jose to Chicago Midway.
Search Deals
Price to beat on a one-way flight from San Jose to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Midway 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 7, 2025.
Use the filters below to find and compare flights from San Jose to Chicago Midway Airport that are best for you.

Fly from

San Jose

Fly to

Midway

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 1/5

6:35 am-3:30 pm

1 stop6h 55m

Chicago Midway

Wed 1/7

8:10 am-2:15 pm

2 stops8h 05m

$371

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 4/11

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Sat 4/18

6:45 am-11:05 am

1 stop6h 20m

$397

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 3/17

11:05 am-5:10 pm

Nonstop4h 05m

Chicago Midway

Tue 3/24

5:45 am-10:30 am

1 stop6h 45m

$397

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 1/16

8:05 am-5:10 pm

1 stop7h 05m

Chicago Midway

Mon 1/19

8:05 am-10:55 am

Nonstop4h 50m

$399

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 3/12

2:30 pm-10:35 pm

1 stop6h 05m

Chicago Midway

Tue 3/17

5:10 pm-11:10 pm

1 stop8h 00m

$407

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 3/16

10:45 pm-9:55 am

1 stop9h 10m

Chicago Midway

Mon 3/23

9:30 am-10:02 pm

2 stops14h 32m

$412

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 1/20

8:05 pm-9:53 am

2 stops11h 48m

Chicago Midway

Tue 1/27

12:48 pm-9:20 pm

1 stop10h 32m

$412

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/15

7:20 am-4:55 pm

2 stops7h 35m

Chicago Midway

Mon 1/19

8:05 am-12:45 pm

1 stop6h 40m

$412

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 3/17

1:15 pm-10:29 pm

1 stop7h 14m

Chicago Midway

Mon 3/23

2:03 pm-8:34 pm

1 stop8h 31m

$427

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 2/11

6:30 am-4:45 pm

1 stop8h 15m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Showing 1-10 of 21 results
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Compare providers for flights from San Jose to Midway

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

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

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

Currently, January is the cheapest month in which you can book a flight from San Jose, California to Chicago Midway Airport (average of $146). Flying from San Jose, California to Chicago Midway Airport in June is currently the most expensive (average of $242). 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 SJC to MDW?

Find hourly flight availability from San Jose to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 7, 2025.

A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 7, 2025.
Peruse reviews from past customers who have flown with Southwest and United Airlines from San Jose to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,078 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

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

    San Jose (SJC) is the airport you will fly out of if you book a flight from San Jose to Chicago Midway. You should not have trouble finding flights to Chicago Midway from San Jose; the airport handles an average of 1 outbound flight to Chicago Midway per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the San Jose airport to Chicago Midway. It is only a 2.9 mi journey to San Jose (SJC) from San Jose’s city center.

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

    For as low as $371, Southwest can have you in Chicago Midway Airport from San Jose, California in 6h 55m. The distance between San Jose, California and Chicago Midway Airport is about 1832 mi.

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

    Cheapflights users have booked flights from San Jose, California to Chicago Midway Airport round-trip from $287. Another airline that can offer you cheap pricing is Southwest. United Airlines is 40% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Looking at all options, your cheapest flight can be booked for $125. While the most popular route (San Jose - Chicago Midway) can be booked for $201 on average, our data indicates $490 when flying from San Jose, California to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from San Jose, California to Chicago Midway Airport (average of $146). Flying from San Jose, California to Chicago Midway Airport in June is currently the most expensive (average of $242). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from San Jose to Midway

Discover the top 2 airlines that operate flights from San Jose to Midway. 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 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$287Average$472FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$330Average$508FlexibilityNo cancel feeOn-time63%

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