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Cheap flights from Chicago to San Jose from $83

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 5/12. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San Jose.
Spirit Airlines Logo
6:59 pm - 3:38 pmORD-SJC
22h 39m2 stops
Spirit Airlines Logo
4:28 pm - 5:25 amSJC-ORD
10h 57m1 stop
$164Spirit Airlines
Find Deal
Thu, May 8 - Tue, May 13
Spirit Airlines Logo
9:02 pm - 10:05 amORD-SJC
15h 03m1 stop
Spirit Airlines Logo
4:28 pm - 5:25 amSJC-ORD
10h 57m1 stop
$170Spirit Airlines
Find Deal
Mon, May 12 - Tue, May 13
Frontier Logo
6:15 am - 6:41 pmMDW-SJC
14h 26m1 stop
Frontier Logo
7:41 pm - 2:48 pmSJC-MDW
17h 07m1 stop
$200Frontier
Find Deal
Mon, May 5 - Thu, May 8
Frontier Logo
6:15 am - 6:41 pmMDW-SJC
14h 26m1 stop
Frontier Logo
12:20 pm - 7:08 pmSJC-MDW
28h 48m1 stop
$201Frontier
Find Deal
Fri, May 2 - Sun, May 4
United Airlines Logo
7:55 pm - 10:54 pmORD-SJC
4h 59mnonstop
United Airlines Logo
6:20 am - 12:43 pmSJC-ORD
4h 23mnonstop
$311United Airlines
Find Deal
Wed, May 14 - Wed, May 21
Delta Logo
7:15 am - 1:45 pmORD-SJC
8h 30m1 stop
Delta Logo
9:00 am - 9:40 pmSJC-ORD
10h 40m2 stops
$328Delta
Find Deal
Wed, May 21 - Sun, May 25
United Airlines Logo
7:55 pm - 10:54 pmORD-SJC
4h 59mnonstop
United Airlines Logo
6:20 am - 12:43 pmSJC-ORD
4h 23mnonstop
$331United Airlines
Find Deal
Thu, May 8 - Tue, May 13
Delta Logo
3:45 pm - 8:31 pmORD-SJC
6h 46m1 stop
Delta Logo
11:44 am - 11:59 pmSJC-ORD
10h 15m1 stop
$337Delta
Find Deal
Sat, May 31 - Sat, Jun 7
Southwest Logo
4:30 pm - 7:05 pmMDW-SJC
4h 35mnonstop
Southwest Logo
8:45 pm - 5:15 amSJC-MDW
6h 30m1 stop
$341Southwest
Find Deal
Sat, May 10 - Mon, May 12
Southwest Logo
4:00 pm - 9:40 pmMDW-SJC
7h 40m2 stops
Southwest Logo
10:25 am - 4:35 pmSJC-MDW
4h 10mnonstop
$346Southwest
Find Deal
Wed, Aug 27 - Sun, Aug 31

United Airlines flights from Chicago to San Jose

Our best United Airlines deals on Chicago to San Jose flight tickets
United Airlines
May 14
ORD7:55 pmChicago O'Hare Intl
4h 59m
SJC10:54 pmSan Jose
May 21
SJC6:20 amSan Jose
4h 23m
ORD12:43 pmChicago O'Hare Intl
United Airlines
May 8
ORD7:55 pmChicago O'Hare Intl
4h 59m
SJC10:54 pmSan Jose
May 13
SJC6:20 amSan Jose
4h 23m
ORD12:43 pmChicago O'Hare Intl
United Airlines
May 8
ORD7:55 pmChicago O'Hare Intl
4h 59m
SJC10:54 pmSan Jose
May 13
SJC8:30 amSan Jose
7h 52m
1 stop
ORD6:22 pmChicago O'Hare Intl

Alaska Airlines flights from Chicago to San Jose

Our best Alaska Airlines deals on Chicago to San Jose flight tickets
Alaska Airlines
May 14
ORD7:19 pmChicago O'Hare Intl
15h 53m
1 stop
SJC9:12 amSan Jose
May 21
SJC9:23 amSan Jose
12h 33m
1 stop
ORD11:56 pmChicago O'Hare Intl
Alaska Airlines
Jun 7
ORD6:00 amChicago O'Hare Intl
10h 55m
1 stop
SJC2:55 pmSan Jose
Jun 11
SJC1:31 pmSan Jose
8h 28m
1 stop
ORD11:59 pmChicago O'Hare Intl
Alaska Airlines
May 25
ORD6:00 amChicago O'Hare Intl
8h 36m
1 stop
SJC12:36 pmSan Jose
May 25
SJC3:45 pmSan Jose
11h 55m
1 stop
ORD5:40 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 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 August is also cheap. Prices for this month can be found on momondo for an average of $369.

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 $450. 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 $588.

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 $450. In contrast, the most expensive time of day to depart to San Jose is in the morning when prices are around $513.

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?

You are more likely to see cheaper flights to San Jose from Chicago when booking 20 weeks ahead of your departure date. In general, you can expect to find flights to San Jose for around $410 when searching 20 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 $276 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.

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

As of April 2025, prices for Chicago to San Jose flights are approximately 27% 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

$83

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 $83. The best round-trip flight deal from Chicago to San Jose found on momondo in the last 72 hours is $164.
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)

  • 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
6.0
3,281 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $133Free CancellationRating
6.3
7,926 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $140Free CancellationRating
8.0
9,882 reviews
Search Alaska Airlines flights
DeltaPriceFrom $274Free CancellationRating
8.0
7,917 reviews
Search Delta flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
8,667 reviews
Search United Airlines flights
SouthwestPriceFrom $353Free CancellationRating
8.0
4,280 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 $353 round-trip. Over the 19 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 8,667 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to San Jose about 7 times each week, with ticket deals ranging from $289 to $495. 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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