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Midway

$91+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 11, 2025.

Round-trip from

$213
(Southwest)

One-way from

$91
(Frontier)

Popular in

August

Cheapest in

November

Average price

$398

Good round-trip deal

$301 or less

Good one-way deal

$169 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. 4% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 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 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:00 amSJC - MDW
1 stop7h 00mSouthwest
Sun 11/97:50 amMDW - SJC
Nonstop4h 45mSouthwest
Deal found 9/11$213
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 10/257:20 amSJC - MDW
1 stop6h 55mSouthwest
Sat 11/14:10 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 9/10$215
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:35 pmSJC - MDW
1 stop9h 49mFrontier
Sat 10/255:20 pmMDW - SJC
2 stops20h 12mFrontier
Deal found 9/10$223
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sun 10/196:35 amSJC - MDW
Nonstop4h 10mSouthwest
Sat 10/252:15 pmMDW - SJC
1 stop6h 35mSouthwest
Deal found 9/10$226
This Southwest deal was found by Cheapflights users on 9/9. 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 10/287:30 amSJC - MDW
Nonstop4h 05mSouthwest
Thu 10/305:05 amMDW - SJC
1 stop6h 15mSouthwest
Deal found 9/9$228
This Southwest deal was found by Cheapflights users on 9/10. 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.
Mon 10/209:00 pmSJC - MDW
1 stop6h 00mSouthwest
Sat 10/254:10 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 9/10$233
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:30 amSJC - MDW
Nonstop4h 10mSouthwest
Sat 11/84:30 pmMDW - SJC
1 stop7h 50mSouthwest
Deal found 9/11$237
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/256:35 amSJC - MDW
2 stops13h 23mMultiple Airlines
Mon 9/297:03 pmMDW - SJC
1 stop17h 42mMultiple Airlines
Deal found 9/9$244
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/158:35 pmSJC - MDW
1 stop6h 40mSouthwest
Sat 10/188:25 amMDW - SJC
1 stop6h 15mSouthwest
Deal found 9/10$246
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sun 10/196:35 amSJC - MDW
Nonstop4h 10mSouthwest
Thu 10/235:45 amMDW - SJC
1 stop6h 45mSouthwest
Deal found 9/10$249

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 11, 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

Thu 11/27

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Tue 12/2

9:35 am-3:00 pm

1 stop7h 25m

$213

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$226

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Thu 10/23

5:45 am-10:30 am

1 stop6h 45m

$249

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 2/24

10:30 pm-9:56 am

1 stop9h 26m

Chicago Midway

Wed 2/25

2:00 pm-9:06 pm

1 stop9h 06m

$257

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Fri 10/24

7:50 am-10:20 am

Nonstop4h 30m

$257

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/5

6:20 am-5:35 pm

1 stop9h 15m

Chicago Midway

Tue 10/7

6:00 am-2:42 pm

2 stops10h 42m

$262

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 12/12

7:45 pm-9:19 am

2 stops11h 34m

Chicago Midway

Mon 12/15

1:50 pm-11:59 pm

2 stops12h 09m

$267

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 10/24

4:00 pm-11:30 pm

1 stop5h 30m

Chicago Midway

Tue 10/28

5:25 pm-7:55 pm

Nonstop4h 30m

$272

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 11/8

12:40 pm-10:14 pm

1 stop7h 34m

Chicago Midway

Tue 11/11

1:47 pm-8:35 pm

1 stop8h 48m

$277

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 10/20

4:00 pm-11:30 pm

1 stop5h 30m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 19 results
1
2

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 11, 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 25% 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 11, 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
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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?

    Southwest and Delta can get you from San Jose to Chicago Midway Airport in just under 4h 10m. Your travel time can differ by up to 5h 16m. 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 $181 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$252FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$331Average$492FlexibilityNo cancel feeOn-time63%

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