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Cheap flights from Chicago to San Jose from $89

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 3/15. 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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Find the cheapest flights from Chicago to San Jose

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:10 am - 5:44 pm
ORD
-
SJC
35h 34m
2 stops
Frontier Logo
8:20 pm - 6:08 am
SJC
-
ORD
7h 48m
1 stop
$183Frontier
Wed, Mar 4 - Mon, Mar 9
Frontier Logo
11:51 am - 5:54 pm
ORD
-
SJC
8h 03m
1 stop
Frontier Logo
10:34 am - 5:26 pm
SJC
-
ORD
28h 52m
1 stop
$195Frontier
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
3:07 pm - 9:47 am
ORD
-
SJC
20h 40m
1 stop
Multiple Airlines Logo
10:34 am - 5:26 pm
SJC
-
ORD
28h 52m
1 stop
$227Multiple Airlines
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
8:20 am - 5:33 pm
ORD
-
SJC
11h 13m
1 stop
Multiple Airlines Logo
7:02 pm - 4:49 am
SJC
-
ORD
7h 47m
1 stop
$233Multiple Airlines
Wed, Mar 4 - Mon, Mar 9
Alaska Airlines Logo
3:07 pm - 10:56 pm
ORD
-
SJC
9h 49m
1 stop
Alaska Airlines Logo
7:00 am - 11:59 pm
SJC
-
ORD
14h 59m
1 stop
$237Alaska Airlines
Tue, Mar 10 - Tue, Mar 17
Alaska Airlines Logo
3:07 pm - 12:08 pm
ORD
-
SJC
23h 01m
1 stop
Alaska Airlines Logo
2:50 pm - 11:59 pm
SJC
-
ORD
7h 09m
1 stop
$240Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
10:30 am - 1:10 pm
MDW
-
SJC
4h 40mnonstop
Southwest Logo
11:05 am - 5:10 pm
SJC
-
MDW
4h 05mnonstop
$297Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
10:30 am - 1:10 pm
MDW
-
SJC
4h 40mnonstop
Southwest Logo
9:30 pm - 5:20 am
SJC
-
MDW
5h 50m
1 stop
$307Southwest
Tue, Mar 10 - Tue, Mar 17
Delta Logo
2:12 pm - 8:37 pm
MDW
-
SJC
8h 25m
1 stop
Delta Logo
8:05 pm - 8:42 am
SJC
-
MDW
10h 37m
2 stops
$322Delta
Tue, May 5 - Tue, May 12
Delta Logo
1:23 pm - 10:37 pm
MDW
-
SJC
11h 14m
2 stops
Delta Logo
8:05 pm - 8:42 am
SJC
-
MDW
10h 37m
2 stops
$328Delta
Tue, May 5 - Wed, May 6

Frontier flights from Chicago to San Jose, California

Our best Frontier deals on Chicago to San Jose, California flight tickets
Frontier
Mar 4
ORD8:10 amChicago O'Hare Intl
35h 34m
2 stops
SJC5:44 pmSan Jose
Mar 9
SJC8:20 pmSan Jose
7h 48m
1 stop
ORD6:08 amChicago O'Hare Intl
$183
Frontier
Feb 19
ORD11:51 amChicago O'Hare Intl
8h 03m
1 stop
SJC5:54 pmSan Jose
Feb 26
SJC10:34 amSan Jose
28h 52m
1 stop
ORD5:26 pmChicago O'Hare Intl
$195
Frontier
Apr 15
ORD9:18 pmChicago O'Hare Intl
22h 44m
1 stop
SJC6:02 pmSan Jose
Apr 19
SJC7:02 pmSan Jose
8h 48m
1 stop
ORD5:50 amChicago O'Hare Intl
$215

Alaska Airlines flights from Chicago to San Jose, California

Our best Alaska Airlines deals on Chicago to San Jose, California flight tickets
Alaska Airlines
Mar 10
ORD3:07 pmChicago O'Hare Intl
9h 49m
1 stop
SJC10:56 pmSan Jose
Mar 17
SJC7:00 amSan Jose
14h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
$237
Alaska Airlines
Feb 24
ORD3:07 pmChicago O'Hare Intl
23h 01m
1 stop
SJC12:08 pmSan Jose
Mar 3
SJC2:50 pmSan Jose
7h 09m
1 stop
ORD11:59 pmChicago O'Hare Intl
$240
Alaska Airlines
Apr 21
ORD7:24 pmChicago O'Hare Intl
16h 06m
1 stop
SJC9:30 amSan Jose
May 12
SJC10:21 amSan Jose
6h 42m
1 stop
ORD7:03 pmChicago O'Hare Intl
$247

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 January 28, 2026.
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

Wed 3/4

8:10 am-5:44 pm

2 stops35h 34m

San Jose

Mon 3/9

8:20 pm-6:08 am

1 stop7h 48m

$183

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Thu 2/19

11:51 am-5:54 pm

1 stop8h 03m

San Jose

Thu 2/26

10:34 am-5:26 pm

1 stop28h 52m

$195

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Mon 2/23

3:07 pm-9:47 am

1 stop20h 40m

San Jose

Thu 2/26

10:34 am-5:26 pm

1 stop28h 52m

$227

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 3/4

8:20 am-5:33 pm

1 stop11h 13m

San Jose

Mon 3/9

7:02 pm-4:49 am

1 stop7h 47m

$233

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 3/10

3:07 pm-10:56 pm

1 stop9h 49m

San Jose

Tue 3/17

7:00 am-11:59 pm

1 stop14h 59m

$237

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 2/24

3:07 pm-12:08 pm

1 stop23h 01m

San Jose

Tue 3/3

2:50 pm-11:59 pm

1 stop7h 09m

$240

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 3/10

10:30 am-1:10 pm

Nonstop4h 40m

San Jose

Tue 3/17

11:05 am-5:10 pm

Nonstop4h 05m

$297

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 3/10

10:30 am-1:10 pm

Nonstop4h 40m

San Jose

Tue 3/17

9:30 pm-5:20 am

1 stop5h 50m

$307

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 5/5

2:12 pm-8:37 pm

1 stop8h 25m

San Jose

Tue 5/12

8:05 pm-8:42 am

2 stops10h 37m

$322

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 5/5

1:23 pm-10:37 pm

2 stops11h 14m

San Jose

Wed 5/6

8:05 pm-8:42 am

2 stops10h 37m

$328

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 October is, on average, the cheapest month to fly to San Jose, California from Chicago, with most prices found around $380. If you are unable to visit San Jose, California during the month of October, then departing from Chicago during the month November is also very affordable. Most momondo users find prices during this month for around $384.

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 $437. 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 $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 $428. 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 $422 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 $336 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 22% 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 January 2026, prices for Chicago to San Jose, California flights are approximately 151% 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

$193

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 in the past 72 hours is $193. The best round-trip flight deal from Chicago to San Jose, California found on momondo in the last 72 hours is $380.
The fastest flight from Chicago to San Jose, California takes 4h 30m
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 30m, 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
5.7
3,056 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $133Free CancellationRating
6.3
8,388 reviews
Search Spirit Airlines flights
DeltaPriceFrom $189Free CancellationRating
7.9
8,124 reviews
Search Delta flights
Alaska AirlinesPriceFrom $262Free CancellationRating
8.0
11,801 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $331Free CancellationRating
7.4
9,210 reviews
Search United Airlines flights
SouthwestPriceFrom $333Free CancellationRating
8.0
4,268 reviews
Search Southwest flights
American AirlinesPriceFrom $370Free CancellationRating
7.2
11,201 reviews
Search American Airlines flights

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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