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$73+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
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 noviembre 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

March

Round-trip from

$168
(Frontier)

One-way from

$73
(Trip.com)
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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High demand for flights, 33% potential price rise
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Best time to find cheap flights, 54% potential price drop
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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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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 noviembre 20, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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.
vie. 12/132:28 pmSJC - MDW
1 stop7h 45mFrontier
lun. 12/167:15 amMDW - SJC
1 stop6h 53mFrontier
Deal found 11/20$168
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/296:06 pmSJC - MDW
2 stops33h 27mMultiple Airlines
mar. 1/78:15 amMDW - SJC
2 stops17h 31mMultiple Airlines
Deal found 11/18$212
This Delta deal was found by Cheapflights users on 11/19. 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.
mar. 12/1012:35 pmSJC - MDW
1 stop7h 31mDelta
vie. 12/132:15 pmMDW - SJC
1 stop8h 52mDelta
Deal found 11/19$346
This Southwest deal was found by Cheapflights users on 11/18. 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.
lun. 12/304:45 pmSJC - MDW
1 stop6h 30mSouthwest
mar. 1/78:35 amMDW - SJC
Nonstop4h 50mSouthwest
Deal found 11/18$418
This Mytrip deal was found by Cheapflights users on 11/19. 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.
mié. 11/205:26 pmSJC - MDW
1 stop14h 02mVolaris
jue. 11/2110:41 pmMDW - SJC
1 stop17h 28mVolaris
Deal found 11/19$776

Find flights from San Jose to Midway within your budget

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

vie. 12/13

2:28 pm-12:13 am

1 stop7h 45m

Chicago Midway

dom. 12/15

7:15 am-12:08 pm

1 stop6h 53m

$168

San JoseChicago

SJC - MDW

SJCMDW

San Jose

dom. 12/29

6:06 pm-5:33 am

2 stops33h 27m

Chicago Midway

mar. 1/7

8:15 am-11:46 pm

2 stops17h 31m

$212

San JoseChicago

SJC - MDW

SJCMDW

San Jose

mar. 12/10

12:35 pm-10:06 pm

1 stop7h 31m

Chicago Midway

vie. 12/13

2:15 pm-9:07 pm

1 stop8h 52m

$346

San JoseChicago

SJC - MDW

SJCMDW

San Jose

jue. 1/16

7:40 am-4:35 pm

1 stop6h 55m

Chicago Midway

lun. 1/20

9:45 am-12:35 pm

Nonstop4h 50m

$408

San JoseChicago

SJC - MDW

SJCMDW

San Jose

jue. 1/9

5:23 pm-11:48 am

1 stop16h 25m

$73

San JoseChicago

SJC - MDW

SJCMDW

San Jose

mar. 1/14

10:33 am-12:13 am

2 stops11h 40m

$103

San JoseChicago

SJC - MDW

SJCMDW

San Jose

mar. 12/31

6:15 am-5:11 pm

1 stop8h 56m

$163

San JoseChicago

SJC - MDW

SJCMDW

San Jose

sáb. 1/11

8:00 am-2:05 pm

Nonstop4h 05m

$187

San JoseChicago

SJC - MDW

SJCMDW

San Jose

sáb. 3/8

10:32 am-7:59 pm

3 stops31h 27m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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

Travel insights for flights from San Jose to Midway

Get recent, data-driven insights about flights from San Jose to Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from San Jose to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $159). Flying from San Jose to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 noviembre 20, 2024.

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 37% 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 noviembre 20, 2024.
Peruse reviews from past customers who have flown with Frontier, Delta and Southwest 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
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 $168, 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 62% 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 $73. Delta flights start at $163 while deals on Southwest start at $187 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 $158. While the most popular route (San Jose - Chicago Midway) can be booked for $166 on average our data indicates $387 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, December is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $159). Flying from San Jose to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

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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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$207FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$203Average$517FlexibilityNo cancel feeOn-time69%
DeltaCheapest$313Average$650FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$358Average$483FlexibilityNo cancel feeOn-time63%
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