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Cheap flights from Chicago to San Jose from $55

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 9/9. 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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Find the cheapest flights from Chicago to San Jose (CHI-SJC)

Cheap round-trip flights

Spirit Airlines Logo
9:00 am - 8:00 pmORD-SJC
13h 00m1 stop
Spirit Airlines Logo
6:35 am - 9:32 pmSJC-ORD
12h 57m1 stop
$114Spirit Airlines
Find Deal
Tue, Sep 9 - Wed, Sep 10
Spirit Airlines Logo
9:00 am - 8:00 pmORD-SJC
13h 00m1 stop
Spirit Airlines Logo
11:40 am - 9:32 pmSJC-ORD
7h 52m1 stop
$121Spirit Airlines
Find Deal
Tue, Sep 9 - Wed, Sep 10
Frontier Logo
6:00 am - 11:30 amORD-SJC
7h 30m1 stop
Frontier Logo
12:30 pm - 11:59 pmSJC-ORD
9h 29m1 stop
$158Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Frontier Logo
6:00 am - 11:26 amORD-SJC
7h 26m1 stop
Frontier Logo
12:25 pm - 11:59 pmSJC-ORD
9h 34m1 stop
$159Frontier
Find Deal
Sun, Sep 14 - Mon, Sep 15
Alaska Airlines Logo
7:59 pm - 10:39 pmORD-SJC
28h 40m1 stop
Alaska Airlines Logo
8:05 pm - 6:59 pmSJC-ORD
20h 54m1 stop
$204Alaska Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
Alaska Airlines Logo
7:59 pm - 9:57 amORD-SJC
15h 58m1 stop
Alaska Airlines Logo
6:25 am - 11:59 pmSJC-ORD
15h 34m1 stop
$231Alaska Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Delta Logo
4:31 pm - 10:23 pmMDW-SJC
7h 52m1 stop
Delta Logo
10:30 pm - 9:40 amSJC-MDW
9h 10m1 stop
$269Delta
Find Deal
Sat, Sep 13 - Mon, Sep 22
Delta Logo
1:43 pm - 8:44 pmMDW-SJC
9h 01m1 stop
Delta Logo
8:12 pm - 8:53 amSJC-MDW
10h 41m2 stops
$274Delta
Find Deal
Sat, Sep 13 - Fri, Sep 26
Southwest Logo
8:25 am - 10:55 amMDW-SJC
4h 30mnonstop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$317Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
7:55 pm - 10:25 pmMDW-SJC
4h 30mnonstop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$326Southwest
Find Deal
Thu, Sep 11 - Wed, Sep 24

Frontier flights from Chicago to San Jose

Our best Frontier deals on Chicago to San Jose flight tickets
Frontier
Sep 19
ORD6:00 amChicago O'Hare Intl
7h 30m
1 stop
SJC11:30 amSan Jose
Sep 22
SJC12:30 pmSan Jose
9h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
$158
Find similar
Frontier
Sep 14
ORD6:00 amChicago O'Hare Intl
7h 26m
1 stop
SJC11:26 amSan Jose
Sep 15
SJC12:25 pmSan Jose
9h 34m
1 stop
ORD11:59 pmChicago O'Hare Intl
$159
Find similar
Frontier
Oct 3
ORD6:00 amChicago O'Hare Intl
7h 30m
1 stop
SJC11:30 amSan Jose
Oct 13
SJC12:35 pmSan Jose
10h 24m
1 stop
ORD12:59 amChicago O'Hare Intl
$189
Find similar

Spirit Airlines flights from Chicago to San Jose

Our best Spirit Airlines deals on Chicago to San Jose flight tickets
Spirit Airlines
Sep 9
ORD9:00 amChicago O'Hare Intl
13h 00m
1 stop
SJC8:00 pmSan Jose
Sep 10
SJC6:35 amSan Jose
12h 57m
1 stop
ORD9:32 pmChicago O'Hare Intl
$114
Find similar
Spirit Airlines
Sep 9
ORD9:00 amChicago O'Hare Intl
13h 00m
1 stop
SJC8:00 pmSan Jose
Sep 10
SJC11:40 amSan Jose
7h 52m
1 stop
ORD9:32 pmChicago O'Hare Intl
$121
Find similar
Spirit Airlines
Sep 13
ORD12:46 pmChicago O'Hare Intl
9h 14m
1 stop
SJC8:00 pmSan Jose
Sep 16
SJC11:40 amSan Jose
7h 52m
1 stop
ORD9:32 pmChicago O'Hare Intl
$137
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San Jose 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 21, 2025.
Use the filters below to find and compare flights from Chicago to San Jose that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 9/9

9:00 am-8:00 pm

1 stop13h 00m

San Jose

Wed 9/10

6:35 am-9:32 pm

1 stop12h 57m

$114

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 9/9

9:00 am-8:00 pm

1 stop13h 00m

San Jose

Wed 9/10

11:40 am-9:32 pm

1 stop7h 52m

$121

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Fri 9/19

6:00 am-11:30 am

1 stop7h 30m

San Jose

Mon 9/22

12:30 pm-11:59 pm

1 stop9h 29m

$158

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Sun 9/14

6:00 am-11:26 am

1 stop7h 26m

San Jose

Mon 9/15

12:25 pm-11:59 pm

1 stop9h 34m

$159

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Wed 10/22

7:59 pm-10:39 pm

1 stop28h 40m

San Jose

Mon 10/27

8:05 pm-6:59 pm

1 stop20h 54m

$204

ChicagoSan Jose

ORD - SJC

ORDSJC

Chicago O'Hare Intl

Tue 10/14

7:59 pm-9:57 am

1 stop15h 58m

San Jose

Tue 10/21

6:25 am-11:59 pm

1 stop15h 34m

$231

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 9/13

4:31 pm-10:23 pm

1 stop7h 52m

San Jose

Mon 9/22

10:30 pm-9:40 am

1 stop9h 10m

$269

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 9/13

1:43 pm-8:44 pm

1 stop9h 01m

San Jose

Fri 9/26

8:12 pm-8:53 am

2 stops10h 41m

$274

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 9/23

8:25 am-10:55 am

Nonstop4h 30m

San Jose

Tue 9/30

6:35 am-12:45 pm

Nonstop4h 10m

$317

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 9/11

7:55 pm-10:25 pm

Nonstop4h 30m

San Jose

Wed 9/24

6:35 am-12:45 pm

Nonstop4h 10m

$326

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

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?

In general, October is the cheapest month to fly from Chicago to San Jose. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $335. If you aren’t able to travel to San Jose during the month of October, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $371.

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

The cheapest day to depart on your flight to San Jose is on a Wednesday when prices can be found for as low as $442. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to San Jose on Sunday is $566.

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

Our most recent data shows that the best time of day to fly to San Jose is in the afternoon. Flights from Chicago to San Jose during this time can be as low as $441. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $521.

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 to San Jose?

You are more likely to see cheaper flights to San Jose from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Jose for around $430 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Jose from Chicago for as low as $305 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 flights?

You could potentially save up to 32% on your flight if you consider stops on a Chicago to San Jose flight.

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

As of August 2025, prices for Chicago to San Jose flights are approximately 36% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San Jose

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San Jose according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

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

Best Price Found

$187

Fastest flight time

4h 30m

Direct flights

Every day

Airports in San Jose

1 airport
The best one-way flight to San Jose from Chicago in the past 72 hours is $187. The best round-trip flight deal from Chicago to San Jose found on momondo in the last 72 hours is $365.
The fastest flight from Chicago to San Jose takes 4h 30m
Direct flights go from Chicago to San Jose every day.
There is 1 airport near San Jose: 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?

  • What is the most popular airline from Chicago to San Jose?

Best airlines flying from Chicago to San Jose

Compare and see reviews for airlines that fly from Chicago to San Jose with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $90Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $133Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
DeltaPriceFrom $274Free CancellationRating
7.9
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $332Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
SouthwestPriceFrom $350Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
American AirlinesPriceFrom $370Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to San Jose

    Southwest flight deals from Chicago to San Jose start from $350 round-trip. Over the 16 Southwest flights for this route in a normal week, average airfare is usually $478 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Chicago to San Jose

    Across 8,930 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose about 3 times each week, with ticket deals ranging from $332 to $511. 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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