How many flights depart from Chicago to San Jose, California on average per week?

13 flights are operational weekly from Chicago to San Jose, California as of August 2026. The most popular departure day for this route is Mon, with 31% of flights per week taking off on this day.

What is the cheapest airline that flies from Chicago to San Jose?

Delta, Southwest, and United Airlines are the most popular carriers operating from Chicago to San Jose

Which airport is the most popular layover for flights between Chicago and San Jose, California?

Seattle (SEA) was the most common stop: 56% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Chicago to San Jose, California?

San Diego (SAN) has the shortest average layover time for this route: 0h 47m.

What airlines fly to San Jose, California?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to San Jose, California from Chicago according to our data. United Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to San Jose, California. Keep in mind that there are 7 different airlines that fly to San Jose, California on a routine basis, so you have a few additional options to choose from.

Which layover airport has the shortest travel time from Chicago to San Jose, California?

Flights connecting via San Diego (SAN) have the shortest average one-way travel time: 6h 54m.

How many flights depart from Chicago to San Jose, California on average per day?

The number of flights available between Chicago and San Jose, California is 1 per day as of August 2026. The most frequent departure time is 10:00AM, with 50% of daily flights leaving in the evening.

Which layover airport offers the lowest fares from Chicago to San Jose, California?

Flights via Seattle (SEA) offer the lowest average round-trip price of $324.

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

Prices for flights from Chicago to San Jose Airport refresh daily.

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

As of August 2026, there are 5 operators available to choose from for flights from Chicago to San Jose Airport.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Jose Airport.

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

The travel and health documents required for your trip to San Jose Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Jose Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$119 Cheap Flights from Chicago to San Jose, California in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to San Jose

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:30 pm - 11:05 pm

MDW

SJC

4h 35mnonstop

5:15 pm - 12:55 am

SJC

MDW

5h 40m

1 stop

$243Southwest

Wed, Sep 9 - Mon, Oct 12

6:15 am - 10:30 am

MDW

SJC

6h 15m

1 stop

11:00 pm - 5:00 am

SJC

MDW

4h 00mnonstop

$243Southwest

Thu, Sep 10 - Sat, Oct 24

9:00 am - 11:46 am

ORD

SJC

4h 46mnonstop

8:45 am - 7:29 pm

SJC

ORD

8h 44m

1 stop

$247United Airlines

Wed, Sep 9 - Tue, Oct 13

2:32 pm - 8:57 pm

ORD

SJC

8h 25m

1 stop

6:30 am - 12:55 pm

SJC

ORD

4h 25mnonstop

$247United Airlines

Tue, Sep 15 - Tue, Sep 22

6:01 am - 10:59 am

ORD

SJC

6h 58m

1 stop

8:29 am - 7:21 pm

SJC

ORD

8h 52m

1 stop

$247Alaska Airlines

Thu, Aug 20 - Wed, Aug 26

6:20 am - 11:24 am

ORD

SJC

7h 04m

1 stop

8:14 pm - 6:17 am

SJC

ORD

8h 03m

1 stop

$249Multiple Airlines

Mon, Aug 17 - Mon, Aug 24

5:00 am - 10:53 am

ORD

SJC

7h 53m

1 stop

12:02 pm - 9:09 pm

SJC

ORD

7h 07m

1 stop

$256American Airlines

Sat, Sep 12 - Sat, Sep 19

2:18 pm - 7:09 pm

ORD

SJC

6h 51m

1 stop

5:15 pm - 1:25 pm

SJC

ORD

18h 10m

1 stop

$257Alaska Airlines

Wed, Sep 9 - Mon, Oct 12

6:30 am - 7:53 pm

ORD

SJC

15h 23m

2 stops

1:38 pm - 5:38 am

SJC

ORD

14h 00m

1 stop

$257Frontier

Thu, Oct 1 - Mon, Oct 5

1:30 pm - 6:26 pm

ORD

SJC

6h 56m

1 stop

2:48 pm - 12:14 am

SJC

ORD

7h 26m

1 stop

$257American Airlines

Thu, Sep 10 - Mon, Sep 14

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Southwest flights from Chicago to San Jose, California

Our best Southwest deals on Chicago to San Jose, California flight tickets

Southwest

Sep 10

MDW6:15 amChicago Midway

6h 15m

1 stop

SJC10:30 amSan Jose

Sep 17

SJC11:00 pmSan Jose

4h 00m

MDW5:00 amChicago Midway

$243

Southwest

Aug 20

MDW8:50 pmChicago Midway

4h 30m

SJC11:20 pmSan Jose

Aug 26

SJC7:00 pmSan Jose

7h 30m

1 stop

MDW4:30 amChicago Midway

$247

Southwest

Sep 9

MDW6:50 amChicago Midway

8h 00m

2 stops

SJC12:50 pmSan Jose

Oct 24

SJC9:05 amSan Jose

4h 00m

MDW3:05 pmChicago Midway

$252

Alaska Airlines flights from Chicago to San Jose, California

Our best Alaska Airlines deals on Chicago to San Jose, California flight tickets

Alaska Airlines

Sep 11

ORD7:20 amChicago O'Hare Intl

8h 25m

1 stop

SJC1:45 pmSan Jose

Sep 18

SJC8:29 amSan Jose

8h 52m

1 stop

ORD7:21 pmChicago O'Hare Intl

$276

Alaska Airlines

Sep 11

ORD7:20 amChicago O'Hare Intl

8h 25m

1 stop

SJC1:45 pmSan Jose

Sep 18

SJC7:29 amSan Jose

9h 52m

1 stop

ORD7:21 pmChicago O'Hare Intl

$292

Alaska Airlines

Sep 18

ORD2:18 pmChicago O'Hare Intl

6h 51m

1 stop

SJC7:09 pmSan Jose

Sep 23

SJC8:29 amSan Jose

8h 52m

1 stop

ORD7:21 pmChicago O'Hare Intl

$297

momondo Fare Finder

Use the filters below to find and compare flights from Chicago 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

Wed 9/9

8:30 pm-11:05 pm

Nonstop4h 35m

San Jose

Mon 10/12

5:15 pm-12:55 am

1 stop5h 40m

$243

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 9/10

6:15 am-10:30 am

1 stop6h 15m

San Jose

Sat 10/24

11:00 pm-5:00 am

Nonstop4h 00m

$243

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 9/9

9:00 am-11:46 am

Nonstop4h 46m

San Jose

Tue 10/13

8:45 am-7:29 pm

1 stop8h 44m

$247

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 9/15

2:32 pm-8:57 pm

1 stop8h 25m

San Jose

Tue 9/22

6:30 am-12:55 pm

Nonstop4h 25m

$247

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 8/20

6:01 am-10:59 am

1 stop6h 58m

San Jose

Wed 8/26

8:29 am-7:21 pm

1 stop8h 52m

$247

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Mon 8/17

6:20 am-11:24 am

1 stop7h 04m

San Jose

Mon 8/24

8:14 pm-6:17 am

1 stop8h 03m

$249

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 9/12

5:00 am-10:53 am

1 stop7h 53m

San Jose

Sat 9/19

12:02 pm-9:09 pm

1 stop7h 07m

$256

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 9/9

2:18 pm-7:09 pm

1 stop6h 51m

San Jose

Mon 10/12

5:15 pm-1:25 pm

1 stop18h 10m

$257

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 10/1

6:30 am-7:53 pm

2 stops15h 23m

San Jose

Mon 10/5

1:38 pm-5:38 am

1 stop14h 00m

$257

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 9/10

1:30 pm-6:26 pm

1 stop6h 56m

San Jose

Mon 9/14

2:48 pm-12:14 am

1 stop7h 26m

$257

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago 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

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and San Jose, California?

Prices are currently low for flights on this route.

Typical prices usually range from $382 to $539.
The lowest price recently found on this route was $243.

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

The month of October is, on average, the cheapest month to fly to San Jose, California from Chicago, with most prices found around $392. If you are unable to visit San Jose, California during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $402.

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 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 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 $394. In the morning is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $507 per ticket.

What is the cheapest Chicago to San Jose flight route?

Fly from Chicago O'Hare Intl to San Jose for the best Chicago - San Jose flight prices

How far in advance should I book a flight from Chicago to San Jose, California?

You are more likely to see cheaper flights to San Jose, California from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Jose, California for around $447 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Jose, California from Chicago for as low as $310 on momondo.

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

There are 3 cabin classes available to choose from on Chicago 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.

How have Chicago to San Jose, California flight prices changed over time?

As of August 2026, prices for Chicago to San Jose, California flights are approximately 35% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San Jose, California

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to San Jose, California (CHI to SJC) flight deals and tips

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

Best Price Found	$168
Fastest flight time	4h 25m
Direct flights	Every day
Airports in San Jose, California	1 airport

The best one-way flight to San Jose, California from Chicago in the past 72 hours is $168. The best round-trip flight deal from Chicago to San Jose, California found on momondo in the last 72 hours is $282.

The fastest flight from Chicago to San Jose, California takes 4h 25m

Direct flights go from Chicago to San Jose, California every day.

There is 1 airport in San Jose, California. From Chicago there are direct flights to San Jose (SJC).

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

How far is Chicago to San Jose by plane?
San Jose is 1836.7 mi away from Chicago. Flights usually cover this in 4h 25m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to San Jose Airport?
Prices for flights from Chicago to San Jose Airport refresh daily.
How many operators does momondo search for flights from Chicago to San Jose Airport?
As of August 2026, there are 5 operators available to choose from for flights from Chicago to San Jose Airport.
How old do you have to be to fly from Chicago to San Jose Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Jose Airport.
What documentation or ID do you need to fly to San Jose Airport?
The travel and health documents required for your trip to San Jose Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Jose Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to San Jose, California?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San Jose, California is Boeing 737 MAX 8 (26.86% of total bookings). The next most popular plane models are Airbus A319 (20.00%), Boeing 737-800 (10.00%), and Boeing 737 (8.00%).
What is the most popular airline from Chicago to San Jose, California?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to San Jose, California is Southwest (55% of total bookings). The next most popular airlines are United Airlines (27%), Alaska Airlines (10%), and Delta (4%).

Best airlines flying from Chicago to San Jose, California

Compare and see reviews for airlines that fly from Chicago to San Jose, California with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $136	Free Cancellation	Rating 7.8 8,497 reviews	Search Delta flights
Alaska Airlines	PriceFrom $232	Free Cancellation	Rating 7.9 12,743 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $272	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights
United Airlines	PriceFrom $291	Free Cancellation	Rating 7.4 10,062 reviews	Search United Airlines flights
Southwest	PriceFrom $298	Free Cancellation	Rating 8.0 4,229 reviews	Search Southwest flights

Southwest Flights From Chicago to San Jose, California
Southwest flight deals from Chicago to San Jose, California start from $298 round-trip. Over the 6 Southwest flights for this route in a normal week, average airfare is usually $484 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Chicago to San Jose, California
Across 10,062 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose, California about 7 times each week, with ticket deals ranging from $291 to $475. Price data is based on momondo searches in the last 72 hours.

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?

momondo does allow users to show only those flights to San Jose from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to San Jose from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to San Jose from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Chicago 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 to San Jose departing on 8/22. 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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Southwest flights from Chicago to San Jose, California

Our best Southwest deals on Chicago to San Jose, California flight tickets

Alaska Airlines flights from Chicago to San Jose, California

Our best Alaska Airlines deals on Chicago to San Jose, California flight tickets

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Use the filters below to find and compare flights from Chicago to San Jose, California that are best for you.

See travel insights to San Jose from

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

What is the typical price of a round-trip flight between Chicago and San Jose, California?

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

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

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

What is the cheapest Chicago to San Jose flight route?

How far in advance should I book a flight from Chicago to San Jose, California?

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

How have Chicago to San Jose, California flight prices changed over time?

What is the cheapest airline that flies from Chicago to San Jose?

What airlines fly to San Jose, California?

Which airport is the most popular layover for flights between Chicago and San Jose, California?

Which layover airport offers the lowest fares from Chicago to San Jose, California?

Which layover airport has the shortest travel time from Chicago to San Jose, California?

Which layover airport has the shortest connection time from Chicago to San Jose, California?

How many flights depart from Chicago to San Jose, California on average per day?

How many flights depart from Chicago to San Jose, California on average per week?

When to book flights from Chicago to San Jose, California

Cheap Chicago to San Jose, California (CHI to SJC) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in San Jose, California

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

Best airlines flying from Chicago to San Jose, California

Compare and see reviews for airlines that fly from Chicago to San Jose, California with momondo

Why use momondo?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing California

Fly your favorite airline to San Jose

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to San Jose

List of cabin classes available on flights landing in San Jose. Availability may vary depending on flight origin and airline.

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