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$101+ Cheap flights from San Jose (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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$264
(Frontier)

One-way from

$101
(Priceline)

Popular in

August

Cheapest in

November

Average price

$538

Good round-trip deal

$350 or less

Good one-way deal

$218 or less
From San Jose to Chicago Midway
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One-way flight from San Jose to Chicago Midway
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Highest demand for flights based on searches. 10% potential increase in price ($54 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 September 2025
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Price to beat on a round-trip flight from San Jose to Chicago Midway.
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Price to beat on a one-way flight from San Jose to Chicago Midway.
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Find 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2411:40 amSJC - MDW
2 stops19h 38mMultiple Airlines
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Deal found 9/14$230
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:12 pmSJC - MDW
1 stop23h 40mMultiple Airlines
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Deal found 9/14$251
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:25 pmSJC - MDW
2 stops20h 03mFrontier
Thu 10/239:26 pmMDW - SJC
2 stops16h 06mFrontier
Deal found 9/14$264
This Delta deal was found by Cheapflights users on 9/16. 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 10/187:35 pmSJC - MDW
2 stops11h 05mDelta
Tue 10/215:04 pmMDW - SJC
1 stop7h 54mDelta
Deal found 9/16$319
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:45 pmSJC - MDW
2 stops13h 43mMultiple Airlines
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Deal found 9/15$331
This Delta deal was found by Cheapflights users on 9/14. 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 11/111:59 pmSJC - MDW
2 stops17h 02mDelta
Tue 11/186:00 amMDW - SJC
2 stops15h 19mDelta
Deal found 9/14$334
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:25 pmSJC - MDW
2 stops20h 03mFrontier
Sun 10/199:26 pmMDW - SJC
2 stops16h 06mFrontier
Deal found 9/14$335
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:12 pmSJC - MDW
1 stop23h 40mMultiple Airlines
Sun 9/281:53 pmMDW - SJC
2 stops22h 52mMultiple Airlines
Deal found 9/14$337

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 September 16, 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

Tue 11/11

9:03 am-9:51 am

2 stops22h 48m

Chicago Midway

Sat 11/15

1:47 pm-8:35 pm

1 stop8h 48m

$356

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/22

9:00 am-8:55 am

2 stops21h 55m

Chicago Midway

Mon 10/27

1:48 pm-8:26 pm

1 stop8h 38m

$356

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 12/3

5:45 am-6:18 pm

2 stops10h 33m

Chicago Midway

Wed 12/10

9:59 am-10:56 pm

2 stops14h 57m

$361

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 12/3

9:04 am-11:32 pm

2 stops12h 28m

Chicago Midway

Tue 12/9

1:14 pm-1:16 pm

2 stops26h 02m

$361

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 10/21

7:30 am-1:35 pm

Nonstop4h 05m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$365

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 10/18

6:45 am-3:10 pm

1 stop6h 25m

Chicago Midway

Wed 10/22

5:25 pm-7:55 pm

Nonstop4h 30m

$369

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 12/5

7:45 pm-9:19 am

2 stops11h 34m

Chicago Midway

Wed 12/10

9:59 am-10:56 pm

2 stops14h 57m

$371

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 12/6

1:59 pm-9:19 am

2 stops17h 20m

Chicago Midway

Sat 12/13

9:59 am-9:43 pm

2 stops13h 44m

$371

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/22

10:15 am-7:25 pm

2 stops7h 10m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$375

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 11/10

7:00 am-8:52 am

2 stops23h 52m

Chicago Midway

Sat 11/15

4:28 pm-10:56 pm

1 stop8h 28m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 results
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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 to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $160). Flying from San Jose to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 16, 2025.

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight in the morning.

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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest and Frontier 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
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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 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 3 outbound flights 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 to Chicago Midway Airport?

    Delta and Southwest can get you from San Jose to Chicago Midway Airport in just under 4h 05m. Your travel time can differ by up to 18h 43m. Airlines will cover a distance of 1832 mi. This flight may include one or multiple stops.

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

    Frontier, at $128, was found to be the cheapest airline from San Jose to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest. Users have found that Frontier is 72% cheaper than the other options available to this destination.

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

    Looking at all options, your cheapest flight can be booked for $142. While the most popular route (San Jose - Chicago Midway) can be booked for $249 on average, our data indicates $331 when flying from San Jose 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 to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $160). Flying from San Jose to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$252FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$331Average$495FlexibilityNo cancel feeOn-time63%

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