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Cheap flights from Chicago Midway Airport to San Jose from $119

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 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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
9:15 pm - 11:50 pm
MDW
-
SJC
4h 35mnonstop
Southwest Logo
5:15 pm - 12:55 am
SJC
-
MDW
5h 40m
1 stop
$243Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
6:05 am - 11:45 am
MDW
-
SJC
7h 40m
1 stop
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
$247Southwest
Thu, Oct 1 - Thu, Oct 1
Southwest Logo
7:00 am - 12:45 pm
MDW
-
SJC
7h 45m
1 stop
Southwest Logo
5:15 pm - 12:55 am
SJC
-
MDW
5h 40m
1 stop
$252Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
11:55 am - 5:05 pm
MDW
-
SJC
7h 10m
1 stop
Southwest Logo
8:55 pm - 5:40 am
SJC
-
MDW
6h 45m
1 stop
$257Southwest
Thu, Oct 1 - Thu, Oct 1
Southwest Logo
1:05 pm - 7:00 pm
MDW
-
SJC
7h 55m
2 stops
Southwest Logo
12:00 pm - 9:20 pm
SJC
-
MDW
7h 20m
2 stops
$267Southwest
Wed, Oct 28 - Wed, Nov 11
Delta Logo
1:00 pm - 10:08 pm
MDW
-
SJC
11h 08m
1 stop
Delta Logo
10:20 pm - 9:52 am
SJC
-
MDW
9h 32m
1 stop
$288Delta
Wed, Dec 9 - Thu, Dec 31
Delta Logo
1:51 pm - 8:24 pm
MDW
-
SJC
8h 33m
1 stop
Delta Logo
12:40 pm - 10:36 pm
SJC
-
MDW
7h 56m
1 stop
$288Delta
Wed, Aug 26 - Tue, Sep 1
Delta Logo
6:00 am - 11:50 am
MDW
-
SJC
7h 50m
1 stop
Delta Logo
10:20 pm - 9:52 am
SJC
-
MDW
9h 32m
1 stop
$288Delta
Tue, Dec 15 - Thu, Dec 31
Delta Logo
1:00 pm - 10:08 pm
MDW
-
SJC
11h 08m
1 stop
Delta Logo
6:30 am - 4:50 pm
SJC
-
MDW
8h 20m
1 stop
$288Delta
Mon, Dec 14 - Thu, Dec 31
Delta Logo
11:28 am - 7:11 pm
MDW
-
SJC
9h 43m
1 stop
Delta Logo
10:20 pm - 9:52 am
SJC
-
MDW
9h 32m
1 stop
$288Delta
Thu, Dec 10 - Thu, Dec 31

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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
MDW1:00 pmChicago Midway
11h 08m
1 stop
SJC10:08 pmSan Jose
Dec 31
SJC10:20 pmSan Jose
9h 32m
1 stop
MDW9:52 amChicago Midway
$288
Delta
Jan 14
MDW6:00 amChicago Midway
7h 56m
1 stop
SJC11:56 amSan Jose
Jan 18
SJC7:00 amSan Jose
7h 25m
1 stop
MDW4:25 pmChicago Midway
$319
Delta
Sep 1
MDW6:05 amChicago Midway
7h 17m
1 stop
SJC11:22 amSan Jose
Sep 5
SJC6:10 amSan Jose
7h 47m
1 stop
MDW3:57 pmChicago Midway
$323

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
Oct 1
MDW9:15 pmChicago Midway
4h 35m
SJC11:50 pmSan Jose
Oct 5
SJC5:15 pmSan Jose
5h 40m
1 stop
MDW12:55 amChicago Midway
$243
Southwest
Oct 1
MDW6:05 amChicago Midway
7h 40m
1 stop
SJC11:45 amSan Jose
Oct 1
SJC11:00 pmSan Jose
4h 00m
MDW5:00 amChicago Midway
$247
Southwest
Oct 1
MDW7:00 amChicago Midway
7h 45m
1 stop
SJC12:45 pmSan Jose
Oct 5
SJC5:15 pmSan Jose
5h 40m
1 stop
MDW12:55 amChicago Midway
$252

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 August 3, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/1

9:15 pm-11:50 pm

Nonstop4h 35m

San Jose

Mon 10/5

5:15 pm-12:55 am

1 stop5h 40m

$243

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/1

6:05 am-11:45 am

1 stop7h 40m

San Jose

Thu 10/1

11:00 pm-5:00 am

Nonstop4h 00m

$247

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/1

7:00 am-12:45 pm

1 stop7h 45m

San Jose

Mon 10/5

5:15 pm-12:55 am

1 stop5h 40m

$252

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/1

11:55 am-5:05 pm

1 stop7h 10m

San Jose

Thu 10/1

8:55 pm-5:40 am

1 stop6h 45m

$257

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/28

1:05 pm-7:00 pm

2 stops7h 55m

San Jose

Wed 11/11

12:00 pm-9:20 pm

2 stops7h 20m

$267

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 12/9

1:00 pm-10:08 pm

1 stop11h 08m

San Jose

Thu 12/31

10:20 pm-9:52 am

1 stop9h 32m

$288

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 8/26

1:51 pm-8:24 pm

1 stop8h 33m

San Jose

Tue 9/1

12:40 pm-10:36 pm

1 stop7h 56m

$288

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 12/15

6:00 am-11:50 am

1 stop7h 50m

San Jose

Thu 12/31

10:20 pm-9:52 am

1 stop9h 32m

$288

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 12/14

1:00 pm-10:08 pm

1 stop11h 08m

San Jose

Thu 12/31

6:30 am-4:50 pm

1 stop8h 20m

$288

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 12/10

11:28 am-7:11 pm

1 stop9h 43m

San Jose

Thu 12/31

10:20 pm-9:52 am

1 stop9h 32m

$288

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 February is, on average, the cheapest month to fly to San Jose, California from Chicago Midway Airport, with most prices found around $0. If you are unable to visit San Jose, California during the month of February, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $285.

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $407. 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 $689.

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 $387. In the morning is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $502 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 Airport to San Jose, California flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to San Jose, California 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San Jose, California.

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

$203

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 $203. The best round-trip flight deal from Chicago Midway Airport to San Jose, California found on momondo in the last 72 hours is $301.
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

Frequently asked questions about flying from Chicago Midway Airport to San Jose, California

  • 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 $298Free CancellationRating
8.0
4,225 reviews
Search Southwest flights

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

    Across 8 Southwest flights from Chicago Midway Airport to San Jose, California this week, the average price was $521, with the best Southwest deals starting from $298 round-trip. 4,225 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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