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Cheap flights from Chicago Midway Airport to San Jose from $71

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Jose departing on 11/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San Jose

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:45 am - 11:30 amMDW-SJC
4h 45mnonstop
Southwest Logo
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
$359Southwest
Find Deal
jue., dic. 4 - mié., dic. 10
Southwest Logo
12:25 pm - 7:00 pmMDW-SJC
8h 35m1 stop
Southwest Logo
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
$369Southwest
Find Deal
jue., dic. 4 - mié., dic. 10
Southwest Logo
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
Southwest Logo
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
$373Southwest
Find Deal
vie., ene. 16 - lun., ene. 19
Southwest Logo
8:45 am - 11:30 amMDW-SJC
4h 45mnonstop
Southwest Logo
6:50 am - 5:00 pmSJC-MDW
8h 10m2 stops
$374Southwest
Find Deal
jue., dic. 4 - mié., dic. 10
Delta Logo
12:50 pm - 8:41 pmMDW-SJC
9h 51m1 stop
Delta Logo
12:55 pm - 11:47 pmSJC-MDW
8h 52m1 stop
$379Delta
Find Deal
mar., dic. 9 - mar., dic. 16
Southwest Logo
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
Southwest Logo
7:50 pm - 5:15 amSJC-MDW
7h 25m1 stop
$383Southwest
Find Deal
vie., ene. 16 - lun., ene. 19
Delta Logo
9:59 am - 7:18 pmMDW-SJC
11h 19m2 stops
Delta Logo
6:35 am - 4:34 pmSJC-MDW
7h 59m1 stop
$384Delta
Find Deal
jue., dic. 4 - mié., dic. 10
Southwest Logo
8:45 am - 11:30 amMDW-SJC
4h 45mnonstop
Southwest Logo
9:00 am - 6:30 pmSJC-MDW
7h 30m2 stops
$388Southwest
Find Deal
jue., dic. 4 - dom., dic. 7
Southwest Logo
1:55 pm - 7:50 pmMDW-SJC
7h 55m2 stops
Southwest Logo
6:50 am - 5:00 pmSJC-MDW
8h 10m2 stops
$389Southwest
Find Deal
jue., dic. 4 - mié., dic. 10
Delta Logo
1:50 pm - 8:36 pmMDW-SJC
8h 46m1 stop
Delta Logo
12:31 pm - 10:22 pmSJC-MDW
7h 51m1 stop
$393Delta
Find Deal
vie., dic. 19 - mié., dic. 31

Southwest flights from Chicago Midway Airport to San Jose, California

Our best Southwest deals on Chicago Midway Airport to San Jose, California flight tickets
Southwest
Dec 4
MDW8:45 amChicago Midway
4h 45m
SJC11:30 amSan Jose
Dec 10
SJC6:30 amSan Jose
4h 10m
MDW12:40 pmChicago Midway
$359
Find similar
Southwest
Dec 4
MDW12:25 pmChicago Midway
8h 35m
1 stop
SJC7:00 pmSan Jose
Dec 10
SJC6:30 amSan Jose
4h 10m
MDW12:40 pmChicago Midway
$369
Find similar
Southwest
Jan 16
MDW8:05 amChicago Midway
4h 50m
SJC10:55 amSan Jose
Jan 19
SJC6:30 amSan Jose
4h 10m
MDW12:40 pmChicago Midway
$373
Find similar

Delta flights from Chicago Midway Airport to San Jose, California

Our best Delta deals on Chicago Midway Airport to San Jose, California flight tickets
Delta
Dec 9
MDW12:50 pmChicago Midway
9h 51m
1 stop
SJC8:41 pmSan Jose
Dec 16
SJC12:55 pmSan Jose
8h 52m
1 stop
MDW11:47 pmChicago Midway
$379
Find similar
Delta
Dec 4
MDW9:59 amChicago Midway
11h 19m
2 stops
SJC7:18 pmSan Jose
Dec 10
SJC6:35 amSan Jose
7h 59m
1 stop
MDW4:34 pmChicago Midway
$384
Find similar
Delta
Dec 19
MDW1:50 pmChicago Midway
8h 46m
1 stop
SJC8:36 pmSan Jose
Dec 31
SJC12:31 pmSan Jose
7h 51m
1 stop
MDW10:22 pmChicago Midway
$393
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Jose, California 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, momondo users made 832,500 searches. Data last updated octubre 27, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Jose, California that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

8:45 am-11:30 am

Nonstop4h 45m

San Jose

mié. 12/10

6:30 am-12:40 pm

Nonstop4h 10m

$359

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

12:25 pm-7:00 pm

1 stop8h 35m

San Jose

mié. 12/10

6:30 am-12:40 pm

Nonstop4h 10m

$369

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

vie. 1/16

8:05 am-10:55 am

Nonstop4h 50m

San Jose

lun. 1/19

6:30 am-12:40 pm

Nonstop4h 10m

$373

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

8:45 am-11:30 am

Nonstop4h 45m

San Jose

mié. 12/10

6:50 am-5:00 pm

2 stops8h 10m

$374

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

mar. 12/9

12:50 pm-8:41 pm

1 stop9h 51m

San Jose

mar. 12/16

12:55 pm-11:47 pm

1 stop8h 52m

$379

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

vie. 1/16

8:05 am-10:55 am

Nonstop4h 50m

San Jose

lun. 1/19

7:50 pm-5:15 am

1 stop7h 25m

$383

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

9:59 am-7:18 pm

2 stops11h 19m

San Jose

mié. 12/10

6:35 am-4:34 pm

1 stop7h 59m

$384

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

8:45 am-11:30 am

Nonstop4h 45m

San Jose

dom. 12/7

9:00 am-6:30 pm

2 stops7h 30m

$388

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

jue. 12/4

1:55 pm-7:50 pm

2 stops7h 55m

San Jose

mié. 12/10

6:50 am-5:00 pm

2 stops8h 10m

$389

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

vie. 12/19

1:50 pm-8:36 pm

1 stop8h 46m

San Jose

mié. 12/31

12:31 pm-10:22 pm

1 stop7h 51m

$393

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Jose from

How to get the cheapest flight ticket from Chicago Midway Airport to San Jose, California

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San Jose, California?

The month of September is, on average, the cheapest month to fly to San Jose, California from Chicago Midway Airport, with most prices found around $365. If you are unable to visit San Jose, California during the month of September, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $382.

What is the cheapest day to depart on your flight to San Jose, California?

On average, the least expensive day to fly to San Jose, California from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $441. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to San Jose, California for around $653.

What is the cheapest time of day to depart on your flight to San Jose, California?

The cheapest time of day to fly to San Jose, California is in the afternoon when flights can be purchased for as low as $435. In the morning is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $514 per ticket.

What is the cheapest Chicago Midway to San Jose flight route?

Fly from Chicago Midway to San Jose for the best Chicago Midway - San Jose flight prices

What cabin class options are available on Chicago Midway to San Jose flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Jose flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to San Jose, California flights?

You could potentially save up to 28% on your flight if you consider stops on a Chicago Midway Airport to San Jose, California flight.

When to book flights from Chicago Midway Airport to San Jose, California

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Jose, California according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San Jose, California (MDW to SJC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Jose, California

Best Price Found

$193

Fastest flight time

4h 30m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in San Jose, California

1 airport
The best one-way flight to San Jose, California from Chicago Midway Airport in the past 72 hours is $193. The best round-trip flight deal from Chicago Midway Airport to San Jose, California found on momondo in the last 72 hours is $456.
The fastest flight from Chicago Midway Airport to San Jose, California takes 4h 30m
Direct flights go from Chicago Midway Airport to San Jose, California on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
There is 1 airport near San Jose, California: San Jose (SJC)
Search flight deals

  • How far is Chicago Midway to San Jose by plane?

    A flight from Chicago Midway to San Jose will travel around 1830.8 mi. A reasonable flight in good conditions will take 4h 40m.

  • When did momondo last update prices for flights from Chicago Midway Airport to San Jose Airport?

    Prices for flights from Chicago Midway Airport to San Jose Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San Jose Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San Jose Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Jose Airport.

  • What documentation or ID do you need to fly to San Jose Airport?

    The travel and health documents you'll need for your trip to San Jose Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Jose Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San Jose, California?

  • What is the most popular airline from Chicago Midway Airport to San Jose, California?

Best airlines flying from Chicago Midway Airport to San Jose, California

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Jose, California with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $333Free CancellationRating
8.0
4,236 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Jose, California

    Across 14 Southwest flights from Chicago Midway Airport to San Jose, California this week, the average price was $458, with the best Southwest deals starting from $333 round-trip. 4,236 users have rated Southwest on momondo, with an average score of 8.0/10.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Jose?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Jose. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to San Jose with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to San Jose flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to San Jose?

Once all potential Chicago to San Jose flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to San Jose right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San Jose flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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mié. 11/26
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