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$160+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$299
(Mytrip)

One-way from

$160
(Delta)

Popular in

January

Cheapest in

November

Average price

$458

Good round-trip deal

$397 or less

Good one-way deal

$216 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 ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:17 pmSJC - MDW
1 stop8h 21mFrontier
Sun 9/147:56 pmMDW - SJC
1 stop17h 36mFrontier
Deal found 6/11$299
This Delta deal was found by Cheapflights users on 6/12. 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 8/126:25 amSJC - MDW
1 stop9h 12mDelta
Wed 8/2012:43 pmMDW - SJC
1 stop9h 04mDelta
Deal found 6/12$319
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/227:00 pmSJC - MDW
1 stop17h 56mMultiple Airlines
Sun 6/297:40 amMDW - SJC
2 stops28h 26mMultiple Airlines
Deal found 6/11$320
This Southwest deal was found by Cheapflights users on 6/12. 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 8/1411:30 amSJC - MDW
1 stop6h 10mSouthwest
Tue 8/1912:45 pmMDW - SJC
1 stop6h 35mSouthwest
Deal found 6/12$366

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 June 12, 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 8/12

6:25 am-5:37 pm

1 stop9h 12m

Chicago Midway

Wed 8/20

12:43 pm-7:47 pm

1 stop9h 04m

$319

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 6/22

7:00 pm-2:56 pm

1 stop17h 56m

Chicago Midway

Sun 6/29

7:40 am-10:06 am

2 stops28h 26m

$320

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 6/26

7:00 pm-2:56 pm

1 stop17h 56m

Chicago Midway

Mon 6/30

6:25 am-1:23 pm

1 stop8h 58m

$343

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 8/14

11:30 am-7:40 pm

1 stop6h 10m

Chicago Midway

Tue 8/19

12:45 pm-5:20 pm

1 stop6h 35m

$366

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 8/13

6:25 am-5:37 pm

1 stop9h 12m

$160

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/4

12:17 pm-10:38 pm

1 stop8h 21m

$170

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 8/25

8:00 am-2:05 pm

Nonstop4h 05m

$176

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 8/24

6:00 am-8:42 am

2 stops24h 42m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 28% on your trip compared to booking a flight in the morning.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from San Jose to Chicago to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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?

    Frontier, at $299, was found to be the cheapest airline from San Jose to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Southwest. Users have found that Frontier is 34% 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 Delta, which is currently one of the cheapest options available, starting at $160. Frontier flights start at $170 while deals on Southwest start at $176 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 $167. While the most popular route (San Jose - Chicago Midway) can be booked for $351 on average our data indicates $355 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
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for San Jose to Midway

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$132Average$252FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$287Average$462FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$358Average$486FlexibilityNo cancel feeOn-time63%

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