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$109+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Jul 13 — Jul 201
Sun 7/13
Sun 7/20
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Chicago Midway are usually found in November or September, booked 23 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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 July 8, 2025.

Round-trip from

$256
(Southwest)

One-way from

$109
(Priceline)

Popular in

January

Cheapest in

November

Average price

$486

Good round-trip deal

$375 or less

Good one-way deal

$185 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. 6% potential increase in price ($32 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 July 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 July 8, 2025.

This Southwest deal was found by Cheapflights users on 7/6. 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.
Thu 10/23:50 pmSJC - MDW
1 stop5h 40mSouthwest
Sun 10/55:45 pmMDW - SJC
Nonstop4h 35mSouthwest
Deal found 7/6$256
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:00 amSJC - MDW
2 stops10h 44mDelta
Sat 8/164:25 pmMDW - SJC
1 stop7h 53mDelta
Deal found 7/7$262
This Frontier deal was found by Cheapflights users on 7/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2412:18 pmSJC - MDW
1 stop6h 36mFrontier
Thu 7/318:38 pmMDW - SJC
2 stops18h 39mFrontier
Deal found 7/6$342

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 July 8, 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 10/2

3:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

Sun 10/5

5:45 pm-8:20 pm

Nonstop4h 35m

$256

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 8/13

9:00 am-9:44 pm

2 stops10h 44m

Chicago Midway

Sat 8/16

4:25 pm-10:18 pm

1 stop7h 53m

$262

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 7/24

12:18 pm-8:54 pm

1 stop6h 36m

Chicago Midway

Thu 7/31

8:38 pm-1:17 pm

2 stops18h 39m

$342

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 7/20

12:18 pm-8:54 pm

1 stop6h 36m

$109

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 8/11

6:00 pm-8:50 am

2 stops12h 50m

$111

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 8/20

3:00 pm-11:00 pm

1 stop6h 00m

$115

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 9/26

6:00 am-8:52 pm

1 stop12h 52m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

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

How far ahead should I book a flight from San Jose to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to Midway. Price data was last updated on June 27, 2025.

To ensure you get the cheapest price possible for a flight from San Jose to Chicago Midway Airport, you should look to book at least 23 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 July 8, 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 26% 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 July 8, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, 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
4,256 reviews

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

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
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

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
7,958 reviews
Southwest
8.0
Very good
4,256 reviews

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

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
5.9
Fair
3,273 reviews
Southwest
8.0
Very good
4,256 reviews

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

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 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 4 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 3 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.

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

    Southwest, at $256, was found to be the cheapest airline from San Jose to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Frontier. Users have found that Southwest is 43% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $109. Delta flights start at $111 while deals on Southwest start at $115 one-way.

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

    Looking at all options, your cheapest flight can be booked for $143. While the most popular route (San Jose - Chicago Midway) can be booked for $210 on average our data indicates $324 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 San Jose?

Book flights to San Jose if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 3 airlines flying from San Jose to Midway

Discover the top 3 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 July 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$132Average$252FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$287Average$462FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$358Average$484FlexibilityNo cancel feeOn-time63%

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