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$138+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
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 April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(CheapOair)

One-way from

$138
(Cheapflightsfares)

Popular in

January

Cheapest in

November

Average price

$417

Good round-trip deal

$413 or less

Good one-way deal

$187 or less
Provider with most accurate pricing for San Jose-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San Jose-Chicago Midway flights.
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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 ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 11, 2025.

This Frontier deal was found by Cheapflights users on 4/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/183:49 pmSJC - MDW
1 stop6h 32mFrontier
Fri 4/256:15 amMDW - SJC
1 stop9h 45mFrontier
Deal found 4/9$260
This Southwest deal was found by Cheapflights users on 4/10. 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.
Tue 5/206:40 amSJC - MDW
Nonstop4h 10mSouthwest
Sat 5/244:30 pmMDW - SJC
Nonstop4h 35mSouthwest
Deal found 4/10$311
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1010:25 pmSJC - MDW
1 stop9h 16mDelta
Tue 6/171:47 pmMDW - SJC
1 stop8h 46mDelta
Deal found 4/10$345
This Trip.com deal was found by Cheapflights users on 4/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:00 amSJC - MDW
2 stops28h 24mMultiple Airlines
Mon 5/196:15 amMDW - SJC
1 stop14h 26mMultiple Airlines
Deal found 4/10$389

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 April 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 5/22

2:33 pm-3:00 pm

1 stop22h 27m

Chicago Midway

Mon 5/26

6:25 am-1:43 pm

1 stop9h 18m

$280

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 5/20

6:40 am-12:50 pm

Nonstop4h 10m

Chicago Midway

Sat 5/24

4:30 pm-7:05 pm

Nonstop4h 35m

$311

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 6/10

10:25 pm-9:41 am

1 stop9h 16m

Chicago Midway

Tue 6/17

1:47 pm-8:33 pm

1 stop8h 46m

$345

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 5/14

6:00 am-12:24 pm

2 stops28h 24m

Chicago Midway

Mon 5/19

6:15 am-6:41 pm

1 stop14h 26m

$389

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 4/18

3:49 pm-12:21 am

1 stop6h 32m

$138

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 5/21

6:40 am-12:50 pm

Nonstop4h 10m

$156

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 4/23

7:54 pm-2:51 pm

1 stop16h 57m

$167

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 5/27

8:05 pm-8:36 am

2 stops10h 31m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/11

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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-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 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 April 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 29% on your trip compared to booking a flight at noon.

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 April 11, 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
4,279 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

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
7,911 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

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
3,277 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

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 1 outbound flight to Chicago Midway per day. You should also have plenty of airline options to choose from since 4 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 $280, was found to be the cheapest airline from San Jose to Chicago Midway Airport.Alternate airlines to your destination round-trip include Southwest and Delta. Users have found that Frontier is 38% 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 $138. Southwest flights start at $156 while deals on Delta start at $171 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 $108. While the most popular route (San Jose - Chicago Midway) can be booked for $180 on average our data indicates $354 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 4 airlines flying from San Jose to Midway

Discover the top 4 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 April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$132Average$238FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$203Average$448FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$650FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$376Average$484FlexibilityNo cancel feeOn-time63%

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