Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to San Jose from $40

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 1/7. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
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.

Find the cheapest flights from Chicago to San Jose

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to San Jose that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San Jose.

Cheap last minute flights

Planning a quick getaway from Chicago to San Jose? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Jose, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San Jose

Find recent round-trip train or bus tickets from Chicago to San Jose.

All round-trip flight deals to San Jose

The cheapest plane tickets to San Jose found on KAYAK recently.
10:47 pm - 10:41 amORD-SJC
13h 54m1 stop
9:34 pm - 5:31 amSJC-ORD
5h 57m1 stop
$123Spirit Airlines
Find Deal
Thu, Jan 30 - Tue, Feb 4
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
1:11 pm - 12:17 amSJC-MDW
9h 06m1 stop
$128Frontier
Find Deal
Thu, Jan 16 - Thu, Jan 23
9:53 pm - 7:46 amORD-SJC
11h 53m1 stop
6:08 pm - 8:10 amSJC-ORD
12h 02m1 stop
$129Spirit Airlines
Find Deal
Mon, Dec 16 - Wed, Dec 18
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
1:11 pm - 12:17 amSJC-MDW
9h 06m1 stop
$129Frontier
Find Deal
Thu, Jan 16 - Thu, Jan 23
7:15 am - 1:43 pmORD-SJC
8h 28m1 stop
2:25 pm - 11:56 pmSJC-ORD
7h 31m1 stop
$295Delta
Find Deal
Wed, Feb 12 - Tue, Feb 18
7:20 pm - 11:52 pmORD-SJC
6h 32m1 stop
2:25 pm - 11:56 pmSJC-ORD
7h 31m1 stop
$311Delta
Find Deal
Tue, Feb 18 - Tue, Feb 25
5:28 pm - 9:14 amORD-SJC
17h 46m1 stop
1:10 pm - 11:59 pmSJC-ORD
8h 49m1 stop
$322Alaska Airlines
Find Deal
Mon, Feb 3 - Tue, Feb 11
5:56 pm - 8:04 amORD-SJC
16h 08m2 stops
8:44 am - 1:04 pmSJC-ORD
26h 20m1 stop
$327Alaska Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18
11:00 am - 3:35 pmMDW-SJC
6h 35m1 stop
6:30 am - 12:35 pmSJC-MDW
4h 05mnonstop
$358Southwest
Find Deal
Fri, Feb 21 - Sat, Mar 1
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
8:55 am - 5:05 pmSJC-MDW
6h 10m1 stop
$363Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
9:54 pm - 9:35 amORD-SJC
13h 41m1 stop
$40Spirit Airlines
Find Deal
Tue, Jan 7
5:25 am - 10:43 amORD-SJC
7h 18m1 stop
$58Spirit Airlines
Find Deal
Thu, Dec 12
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$63Frontier
Find Deal
Mon, Dec 16
7:25 am - 12:11 pmORD-SJC
6h 46m1 stop
$63Frontier
Find Deal
Thu, Jan 23
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$157United Airlines
Find Deal
Wed, Jan 8
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$157Southwest
Find Deal
Tue, Jan 14
1:26 pm - 9:10 pmMDW-SJC
9h 44m1 stop
$163Delta
Find Deal
Wed, Jan 15
5:45 am - 12:10 pmORD-SJC
8h 25m1 stop
$163Delta
Find Deal
Tue, Feb 18
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$177United Airlines
Find Deal
Fri, Jan 10
3:25 pm - 6:10 pmMDW-SJC
4h 45mnonstop
$177Southwest
Find Deal
Sat, Jan 11
7:25 am - 12:08 pmORD-SJC
6h 43m1 stop
8:12 pm - 12:05 pmSJC-ORD
13h 53m1 stop
Sun, Dec 8 - Wed, Dec 11
7:25 am - 12:08 pmORD-SJC
6h 43m1 stop
3:56 pm - 5:30 amSJC-ORD
11h 34m1 stop
Thu, Dec 5 - Mon, Dec 9
9:10 pm - 7:46 amORD-SJC
12h 36m1 stop
8:44 pm - 5:30 amSJC-ORD
6h 46m1 stop
$277Spirit Airlines
Find Deal
Sat, Dec 7 - Sat, Dec 14
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
2:28 pm - 12:13 amSJC-MDW
7h 45m1 stop
$318Frontier
Find Deal
Thu, Dec 5 - Mon, Dec 9
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
2:28 pm - 12:13 amSJC-MDW
7h 45m1 stop
$334Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
9:53 pm - 9:35 amORD-SJC
13h 42m1 stop
8:12 pm - 2:26 pmSJC-ORD
16h 14m2 stops
$338Spirit Airlines
Find Deal
Sun, Dec 8 - Wed, Dec 11
9:05 am - 11:54 amORD-SJC
4h 49mnonstop
10:55 am - 12:22 amSJC-ORD
11h 27m1 stop
$851United Airlines
Find Deal
Fri, Dec 6 - Tue, Dec 10
9:05 am - 11:54 amORD-SJC
4h 49mnonstop
10:55 am - 9:31 amSJC-ORD
20h 36m1 stop
$871United Airlines
Find Deal
Sat, Dec 7 - Mon, Dec 9
8:25 am - 11:10 amMDW-SJC
4h 45mnonstop
9:45 am - 3:50 pmSJC-MDW
4h 05mnonstop
$967Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14
8:25 am - 11:10 amMDW-SJC
4h 45mnonstop
7:55 am - 3:50 pmSJC-MDW
5h 55m1 stop
$976Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$334Southwest
Find Deal
Thu, Jan 16 - Wed, Jan 22
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$353United Airlines
Find Deal
Thu, Jan 16 - Thu, Jan 23
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$354Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$394Southwest
Find Deal
Fri, Feb 14 - Sun, Feb 16
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$403United Airlines
Find Deal
Tue, Feb 4 - Wed, Feb 12
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
6:50 am - 12:55 pmSJC-MDW
4h 05mnonstop
$414Southwest
Find Deal
Fri, Feb 28 - Sat, Mar 8
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$419United Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
9:08 am - 12:03 pmORD-SJC
4h 55mnonstop
6:20 am - 12:35 pmSJC-ORD
4h 15mnonstop
$423United Airlines
Find Deal
Tue, Feb 18 - Sat, Feb 22
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$430Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$433United Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 21

Frontier flights from Chicago to San Jose

Our best Frontier deals on Chicago to San Jose flight tickets
Frontier
Jan 16
MDW7:15 amChicago Midway
6h 56m
1 stop
SJC12:11 pmSan Jose
Jan 23
SJC1:11 pmSan Jose
9h 06m
1 stop
MDW12:17 amChicago Midway
Frontier
Jan 16
MDW7:15 amChicago Midway
6h 56m
1 stop
SJC12:11 pmSan Jose
Jan 23
SJC1:11 pmSan Jose
9h 06m
1 stop
MDW12:17 amChicago Midway
Frontier
Jan 16
MDW7:15 amChicago Midway
6h 56m
1 stop
SJC12:11 pmSan Jose
Jan 23
SJC1:11 pmSan Jose
9h 06m
1 stop
MDW12:17 amChicago Midway

Spirit Airlines flights from Chicago to San Jose

Our best Spirit Airlines deals on Chicago to San Jose flight tickets
Spirit Airlines
Dec 9
ORD9:53 pmChicago O'Hare Intl
11h 53m
1 stop
SJC7:46 amSan Jose
Dec 11
SJC12:23 pmSan Jose
19h 20m
2 stops
ORD9:43 amChicago O'Hare Intl
Spirit Airlines
Jan 30
ORD10:47 pmChicago O'Hare Intl
13h 54m
1 stop
SJC10:41 amSan Jose
Feb 4
SJC9:34 pmSan Jose
5h 57m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Dec 16
ORD9:53 pmChicago O'Hare Intl
11h 53m
1 stop
SJC7:46 amSan Jose
Dec 18
SJC6:08 pmSan Jose
12h 02m
1 stop
ORD8:10 amChicago O'Hare Intl

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 typical price of a round-trip flight between Chicago and San Jose?

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 $289. If you aren’t able to travel to San Jose during the month of October, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $330.

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 Tuesday when prices can be found for as low as $370. 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 Monday as prices are generally higher than usual. According to our data, the average ticket price to San Jose on Monday is $527.

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 at noon. Flights from Chicago to San Jose during this time can be as low as $292. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $450.

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?

We recommend purchasing flights from Chicago to San Jose 22 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San Jose for $406. However, in the past 72 hours, people saw flights from Chicago for as low as $161.

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 78% 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 December 2024, prices for Chicago to San Jose flights are approximately 8% more expensive 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

$40

Fastest flight time

4h 35m

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 $40. The best round-trip flight deal from Chicago to San Jose found on momondo in the last 72 hours is $123.
The fastest flight from Chicago to San Jose takes 4h 35m
Direct flights go from Chicago to San Jose every day.
There is 1 airport near San Jose: San Jose (SJC)

  • How far is Chicago to San Jose by plane?

    San Jose is 1836.7 mi away from Chicago. Flights usually cover this in 4h 35m, 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
6.1
3,508 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $138Free CancellationRating
8.0
9,513 reviews
Search Alaska Airlines flights
Spirit AirlinesPriceFrom $141Free CancellationRating
6.3
8,151 reviews
Search Spirit Airlines flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,698 reviews
Search Delta flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
9,141 reviews
Search United Airlines flights
American AirlinesPriceFrom $314Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $423Free CancellationRating
8.1
4,951 reviews
Search Southwest flights
  • Southwest Flights From Chicago to San Jose

    Southwest flight deals from Chicago to San Jose start from $423 round-trip. Over the 5 Southwest flights for this route in a normal week, average airfare is usually $482 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Chicago to San Jose

    Across 9,141 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose about 4 times each week, with ticket deals ranging from $288 to $494. 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.


An easier way to manage your San Jose 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.
1 adult
From?
To?
Sun 12/8
Sun 12/15
Email me momondo's favorite deals

Find better results for your trip to the United States