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Cheap flights from Chicago to San Jose from $81

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 2/8. 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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0 bags

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Cheap round-trip flights

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Hawaiian Airlines Logo
8:00 am - 2:42 pm
ORD
-
SJC
8h 42m1 stop
Hawaiian Airlines Logo
11:00 am - 11:50 pm
SJC
-
ORD
10h 50m1 stop
$243Hawaiian Airlines
Sat, Jan 24 - Sat, Jan 31
Hawaiian Airlines Logo
9:00 am - 5:34 pm
ORD
-
SJC
10h 34m1 stop
Hawaiian Airlines Logo
11:00 am - 11:50 pm
SJC
-
ORD
10h 50m1 stop
$244Hawaiian Airlines
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
7:57 pm - 6:36 pm
ORD
-
SJC
24h 39m1 stop
Multiple Airlines Logo
7:31 pm - 10:42 pm
SJC
-
ORD
25h 11m2 stops
$246Multiple Airlines
Wed, Jan 7 - Sun, Jan 11
Frontier Logo
8:49 pm - 6:14 pm
ORD
-
SJC
23h 25m1 stop
Frontier Logo
11:14 am - 9:11 pm
SJC
-
ORD
7h 57m1 stop
$259Frontier
Sun, Jan 11 - Thu, Jan 15
Alaska Airlines Logo
3:37 pm - 6:45 pm
ORD
-
SJC
29h 08m1 stop
Alaska Airlines Logo
12:46 pm - 2:29 pm
SJC
-
ORD
23h 43m1 stop
$262Alaska Airlines
Tue, Jan 6 - Tue, Jan 13
Alaska Airlines Logo
8:00 am - 2:42 pm
ORD
-
SJC
8h 42m1 stop
Alaska Airlines Logo
6:15 am - 11:50 pm
SJC
-
ORD
15h 35m1 stop
$263Alaska Airlines
Fri, Jan 23 - Sun, Jan 25
Frontier Logo
10:41 pm - 6:37 pm
ORD
-
SJC
21h 56m1 stop
Frontier Logo
11:14 am - 9:11 pm
SJC
-
ORD
7h 57m1 stop
$268Frontier
Thu, Jan 15 - Sun, Jan 18
Delta Logo
9:33 am - 8:05 pm
MDW
-
SJC
12h 32m2 stops
Delta Logo
7:45 am - 10:22 pm
SJC
-
MDW
12h 37m2 stops
$294Delta
Sat, Jan 24 - Sat, Jan 31
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
$324Delta
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
3:25 pm - 9:55 pm
MDW
-
SJC
8h 30m1 stop
Southwest Logo
8:40 am - 4:35 pm
SJC
-
MDW
5h 55m1 stop
$392Southwest
Thu, Jan 15 - Wed, Jan 21

Southwest flights from Chicago to San Jose, California

Our best Southwest deals on Chicago to San Jose, California flight tickets
Southwest
Jan 15
MDW3:25 pmChicago Midway
8h 30m
1 stop
SJC9:55 pmSan Jose
Jan 21
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
$392
Find similar
Southwest
Jan 28
MDW8:15 amChicago Midway
7h 50m
1 stop
SJC2:05 pmSan Jose
Feb 2
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
$396
Find similar
Southwest
Jan 15
MDW3:25 pmChicago Midway
7h 45m
2 stops
SJC9:10 pmSan Jose
Jan 21
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
$398
Find similar

Delta flights from Chicago to San Jose, California

Our best Delta deals on Chicago to San Jose, California flight tickets
Delta
Jan 18
ORD7:30 amChicago O'Hare Intl
8h 04m
1 stop
SJC1:34 pmSan Jose
Jan 24
SJC2:25 pmSan Jose
7h 28m
1 stop
ORD11:53 pmChicago O'Hare Intl
$273
Find similar
Delta
Jan 7
ORD2:20 pmChicago O'Hare Intl
9h 47m
1 stop
SJC10:07 pmSan Jose
Jan 11
SJC11:40 amSan Jose
10h 13m
1 stop
ORD11:53 pmChicago O'Hare Intl
$283
Find similar
Delta
Jan 6
ORD7:30 amChicago O'Hare Intl
12h 10m
1 stop
SJC5:40 pmSan Jose
Jan 7
SJC7:45 amSan Jose
11h 58m
2 stops
ORD9:43 pmChicago O'Hare Intl
$288
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 11, 2025.
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

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 1/24

8:00 am-2:42 pm

1 stop8h 42m

San Jose

Sat 1/31

11:00 am-11:50 pm

1 stop10h 50m

$243

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sat 1/24

9:00 am-5:34 pm

1 stop10h 34m

San Jose

Sat 1/31

11:00 am-11:50 pm

1 stop10h 50m

$244

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 1/7

7:57 pm-6:36 pm

1 stop24h 39m

San Jose

Sun 1/11

7:31 pm-10:42 pm

2 stops25h 11m

$246

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sun 1/11

8:49 pm-6:14 pm

1 stop23h 25m

San Jose

Thu 1/15

11:14 am-9:11 pm

1 stop7h 57m

$259

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 1/6

3:37 pm-6:45 pm

1 stop29h 08m

San Jose

Tue 1/13

12:46 pm-2:29 pm

1 stop23h 43m

$262

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 1/23

8:00 am-2:42 pm

1 stop8h 42m

San Jose

Sun 1/25

6:15 am-11:50 pm

1 stop15h 35m

$263

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 1/15

10:41 pm-6:37 pm

1 stop21h 56m

San Jose

Sun 1/18

11:14 am-9:11 pm

1 stop7h 57m

$268

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 1/24

9:33 am-8:05 pm

2 stops12h 32m

San Jose

Sat 1/31

7:45 am-10:22 pm

2 stops12h 37m

$294

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 1/15

9:32 am-5:40 pm

2 stops10h 08m

San Jose

Sun 1/18

6:25 pm-8:52 am

2 stops12h 27m

$324

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 1/15

3:25 pm-9:55 pm

1 stop8h 30m

San Jose

Wed 1/21

8:40 am-4:35 pm

1 stop5h 55m

$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 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, with most prices found around $353. If you are unable to visit San Jose, California during the month of February, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around $380.

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 Wednesday. momondo users have found tickets for Wednesday departures for as low as $442. 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 $664.

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 $434. 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 to San Jose flight route?

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

How far in advance should I book a flight 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 $428 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 $338 on momondo.

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

There are 4 cabin classes available to choose from on Chicago 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 to San Jose, California flights?

You could potentially save up to 51% on your flight if you consider stops on a Chicago to San Jose, California flight.

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

As of December 2025, prices for Chicago to San Jose, California flights are approximately 73% more expensive 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

$244

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 $244. The best round-trip flight deal from Chicago to San Jose, California found on momondo in the last 72 hours is $397.
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).
Search flight deals

  • 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?

  • 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?

  • What is the most popular airline 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
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $80Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $142Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $262Free CancellationRating
8.0
11,431 reviews
Search Alaska Airlines flights
DeltaPriceFrom $265Free CancellationRating
7.9
8,005 reviews
Search Delta flights
SouthwestPriceFrom $333Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
United AirlinesPriceFrom $338Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $352Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to San Jose, California

    Southwest flight deals from Chicago to San Jose, California start from $333 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $483 round-trip - but some users have found much cheaper deals with momondo.

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.

An easier way to manage your San Jose, California trip

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