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Cheap flights from Chicago Midway Airport to San Jose from $123

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 1/16. 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.
Delta Logo
1:26 pm - 10:05 pm
MDW
-
SJC
10h 39m2 stops
Delta Logo
10:35 pm - 9:54 am
SJC
-
MDW
9h 19m1 stop
$340Delta
Fri, Feb 20 - Wed, Feb 25
Delta Logo
1:26 pm - 10:05 pm
MDW
-
SJC
10h 39m2 stops
Delta Logo
10:35 pm - 12:46 pm
SJC
-
MDW
12h 11m2 stops
$345Delta
Fri, Feb 20 - Wed, Feb 25
Delta Logo
9:32 am - 5:40 pm
MDW
-
SJC
10h 08m2 stops
Delta Logo
6:25 pm - 8:52 am
SJC
-
MDW
12h 27m2 stops
$354Delta
Wed, Feb 4 - Sun, Feb 8
Delta Logo
9:33 am - 5:40 pm
MDW
-
SJC
10h 07m2 stops
Delta Logo
10:45 pm - 9:53 am
SJC
-
MDW
9h 08m1 stop
$360Delta
Wed, Jan 28 - Mon, Feb 2
Delta Logo
9:33 am - 5:40 pm
MDW
-
SJC
10h 07m2 stops
Delta Logo
8:05 pm - 9:53 am
SJC
-
MDW
11h 48m2 stops
$365Delta
Wed, Jan 28 - Mon, Feb 2
Southwest Logo
8:05 am - 10:55 am
MDW
-
SJC
4h 50mnonstop
Southwest Logo
8:40 am - 4:35 pm
SJC
-
MDW
5h 55m1 stop
$383Southwest
Mon, Feb 9 - Wed, Feb 25
Southwest Logo
8:05 am - 10:55 am
MDW
-
SJC
4h 50mnonstop
Southwest Logo
7:00 am - 1:10 pm
SJC
-
MDW
4h 10mnonstop
$387Southwest
Mon, Feb 9 - Sat, Feb 28
Delta Logo
9:32 am - 5:40 pm
MDW
-
SJC
10h 08m2 stops
Delta Logo
10:45 pm - 9:53 am
SJC
-
MDW
9h 08m1 stop
$390Delta
Wed, Jan 14 - Tue, Jan 20
Southwest Logo
8:00 am - 10:50 am
MDW
-
SJC
4h 50mnonstop
Southwest Logo
6:30 am - 12:40 pm
SJC
-
MDW
4h 10mnonstop
$391Southwest
Fri, Feb 20 - Mon, Feb 23
Delta Logo
1:49 pm - 9:28 pm
MDW
-
SJC
9h 39m1 stop
Delta Logo
8:05 pm - 9:08 am
SJC
-
MDW
11h 03m2 stops
$392Delta
Tue, Jan 20 - Tue, Feb 3

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
Feb 20
MDW1:26 pmChicago Midway
10h 39m
2 stops
SJC10:05 pmSan Jose
Feb 25
SJC10:35 pmSan Jose
9h 19m
1 stop
MDW9:54 amChicago Midway
$340
Find similar
Delta
Feb 20
MDW1:26 pmChicago Midway
10h 39m
2 stops
SJC10:05 pmSan Jose
Feb 25
SJC10:35 pmSan Jose
12h 11m
2 stops
MDW12:46 pmChicago Midway
$345
Find similar
Delta
Feb 4
MDW9:32 amChicago Midway
10h 08m
2 stops
SJC5:40 pmSan Jose
Feb 8
SJC6:25 pmSan Jose
12h 27m
2 stops
MDW8:52 amChicago Midway
$354
Find similar

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
Feb 9
MDW8:05 amChicago Midway
4h 50m
SJC10:55 amSan Jose
Feb 25
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
$383
Find similar
Southwest
Feb 9
MDW8:05 amChicago Midway
4h 50m
SJC10:55 amSan Jose
Feb 28
SJC7:00 amSan Jose
4h 10m
MDW1:10 pmChicago Midway
$387
Find similar
Southwest
Feb 20
MDW8:00 amChicago Midway
4h 50m
SJC10:50 amSan Jose
Feb 23
SJC6:30 amSan Jose
4h 10m
MDW12:40 pmChicago Midway
$391
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 December 26, 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

Fri 2/20

1:26 pm-10:05 pm

2 stops10h 39m

San Jose

Wed 2/25

10:35 pm-9:54 am

1 stop9h 19m

$340

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 2/20

1:26 pm-10:05 pm

2 stops10h 39m

San Jose

Wed 2/25

10:35 pm-12:46 pm

2 stops12h 11m

$345

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 2/4

9:32 am-5:40 pm

2 stops10h 08m

San Jose

Sun 2/8

6:25 pm-8:52 am

2 stops12h 27m

$354

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 1/28

9:33 am-5:40 pm

2 stops10h 07m

San Jose

Mon 2/2

10:45 pm-9:53 am

1 stop9h 08m

$360

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 1/28

9:33 am-5:40 pm

2 stops10h 07m

San Jose

Mon 2/2

8:05 pm-9:53 am

2 stops11h 48m

$365

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 2/9

8:05 am-10:55 am

Nonstop4h 50m

San Jose

Wed 2/25

8:40 am-4:35 pm

1 stop5h 55m

$383

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 2/9

8:05 am-10:55 am

Nonstop4h 50m

San Jose

Sat 2/28

7:00 am-1:10 pm

Nonstop4h 10m

$387

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 1/14

9:32 am-5:40 pm

2 stops10h 08m

San Jose

Tue 1/20

10:45 pm-9:53 am

1 stop9h 08m

$390

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 2/20

8:00 am-10:50 am

Nonstop4h 50m

San Jose

Mon 2/23

6:30 am-12:40 pm

Nonstop4h 10m

$391

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 1/20

1:49 pm-9:28 pm

1 stop9h 39m

San Jose

Tue 2/3

8:05 pm-9:08 am

2 stops11h 03m

$392

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 January is also very affordable. Most momondo users find prices during this month for around $378.

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 $440. 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 $432. In the morning is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $503 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 10% 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

$267

Fastest flight time

4h 30m

Direct flights

Every day

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 $267. The best round-trip flight deal from Chicago Midway Airport to San Jose, California found on momondo in the last 72 hours is $468.
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 every day.
There is 1 airport in San Jose, California. From Chicago Midway Airport there are direct flights to 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 30m.

  • 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
4,258 reviews
Search Southwest flights

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

    Across 10 Southwest flights from Chicago Midway Airport to San Jose, California this week, the average price was $461, with the best Southwest deals starting from $333 round-trip. 4,258 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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