Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to San Jose from $91

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 5/10. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
10:30 am - 5:05 pm
MDW
-
SJC
8h 35m
2 stops
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$328Southwest
Wed, Mar 25 - Mon, Mar 30
Delta Logo
1:10 pm - 10:02 pm
MDW
-
SJC
10h 52m
2 stops
Delta Logo
8:20 pm - 9:06 am
SJC
-
MDW
10h 46m
2 stops
$331Delta
Fri, Apr 10 - Fri, Apr 17
Southwest Logo
6:25 pm - 11:30 pm
MDW
-
SJC
7h 05m
1 stop
Southwest Logo
1:35 pm - 9:30 pm
SJC
-
MDW
5h 55m
1 stop
$332Southwest
Mon, Mar 30 - Wed, Apr 8
Southwest Logo
10:00 am - 2:10 pm
MDW
-
SJC
6h 10m
1 stop
Southwest Logo
9:15 pm - 5:00 am
SJC
-
MDW
5h 45m
1 stop
$333Southwest
Thu, Mar 19 - Tue, Mar 31
Southwest Logo
5:25 am - 10:20 am
MDW
-
SJC
6h 55m
1 stop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$336Southwest
Fri, Apr 10 - Mon, Apr 20
Southwest Logo
5:40 pm - 11:30 pm
MDW
-
SJC
7h 50m
2 stops
Southwest Logo
9:10 pm - 5:00 am
SJC
-
MDW
5h 50m
1 stop
$337Southwest
Sat, Apr 4 - Tue, Apr 7
Southwest Logo
10:30 am - 5:05 pm
MDW
-
SJC
8h 35m
2 stops
Southwest Logo
9:35 pm - 5:20 am
SJC
-
MDW
5h 45m
1 stop
$338Southwest
Wed, Mar 25 - Mon, Mar 30
Southwest Logo
10:20 am - 3:20 pm
MDW
-
SJC
7h 00m
1 stop
Southwest Logo
6:30 am - 5:15 pm
SJC
-
MDW
8h 45m
2 stops
$339Southwest
Wed, Apr 1 - Sat, Apr 18
Southwest Logo
3:05 pm - 9:25 pm
MDW
-
SJC
8h 20m
2 stops
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$340Southwest
Sat, Apr 4 - Sat, Apr 18
Southwest Logo
5:15 pm - 10:00 pm
MDW
-
SJC
6h 45m
1 stop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$341Southwest
Wed, May 6 - Sun, May 10

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
Mar 25
MDW10:30 amChicago Midway
8h 35m
2 stops
SJC5:05 pmSan Jose
Mar 30
SJC10:55 pmSan Jose
4h 05m
MDW5:00 amChicago Midway
$328
Southwest
Mar 30
MDW6:25 pmChicago Midway
7h 05m
1 stop
SJC11:30 pmSan Jose
Apr 8
SJC1:35 pmSan Jose
5h 55m
1 stop
MDW9:30 pmChicago Midway
$332
Southwest
Mar 19
MDW10:00 amChicago Midway
6h 10m
1 stop
SJC2:10 pmSan Jose
Mar 31
SJC9:15 pmSan Jose
5h 45m
1 stop
MDW5:00 amChicago Midway
$333

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
Apr 10
MDW1:10 pmChicago Midway
10h 52m
2 stops
SJC10:02 pmSan Jose
Apr 17
SJC8:20 pmSan Jose
10h 46m
2 stops
MDW9:06 amChicago Midway
$331
Delta
Mar 31
MDW6:00 amChicago Midway
8h 08m
1 stop
SJC12:08 pmSan Jose
Mar 31
SJC6:25 pmSan Jose
12h 28m
2 stops
MDW8:53 amChicago Midway
$363
Delta
May 16
MDW1:59 pmChicago Midway
8h 39m
1 stop
SJC8:38 pmSan Jose
May 21
SJC10:55 pmSan Jose
7h 48m
1 stop
MDW8:43 amChicago Midway
$364

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 February 27, 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

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 3/25

10:30 am-5:05 pm

2 stops8h 35m

San Jose

Mon 3/30

10:55 pm-5:00 am

Nonstop4h 05m

$328

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 4/10

1:10 pm-10:02 pm

2 stops10h 52m

San Jose

Fri 4/17

8:20 pm-9:06 am

2 stops10h 46m

$331

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 3/30

6:25 pm-11:30 pm

1 stop7h 05m

San Jose

Wed 4/8

1:35 pm-9:30 pm

1 stop5h 55m

$332

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 3/19

10:00 am-2:10 pm

1 stop6h 10m

San Jose

Tue 3/31

9:15 pm-5:00 am

1 stop5h 45m

$333

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 4/10

5:25 am-10:20 am

1 stop6h 55m

San Jose

Mon 4/20

10:55 pm-5:00 am

Nonstop4h 05m

$336

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 4/4

5:40 pm-11:30 pm

2 stops7h 50m

San Jose

Tue 4/7

9:10 pm-5:00 am

1 stop5h 50m

$337

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 3/25

10:30 am-5:05 pm

2 stops8h 35m

San Jose

Mon 3/30

9:35 pm-5:20 am

1 stop5h 45m

$338

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 4/1

10:20 am-3:20 pm

1 stop7h 00m

San Jose

Sat 4/18

6:30 am-5:15 pm

2 stops8h 45m

$339

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 4/4

3:05 pm-9:25 pm

2 stops8h 20m

San Jose

Sat 4/18

10:55 pm-5:00 am

Nonstop4h 05m

$340

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 5/6

5:15 pm-10:00 pm

1 stop6h 45m

San Jose

Sun 5/10

10:55 pm-5:00 am

Nonstop4h 05m

$341

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Thursday. momondo users have found tickets for Thursday departures for as low as $433. 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 $623.

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 $429. In the morning is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $475 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?

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

$174

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 $174. The best round-trip flight deal from Chicago Midway Airport to San Jose, California found on momondo in the last 72 hours is $416.
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
4,301 reviews
Search Southwest flights

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

    Across 6 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. 4,301 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.

An easier way to manage your San Jose, California trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 3/29
Sun 4/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States