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Cheap flights from Chicago to San Jose

Chicago
CHI
San Jose
SJC

Flight deals from Chicago to San Jose

Below you can see the best deals on flights Chicago — San Jose for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 11 August, from $123.

Top 10 cheap flights from Chicago to San Jose

AS
$ 121

Chicago — San Diego

14:1816:55
20 Aug 2026
4 h 37 m
Direct flight
AS
$ 121

Chicago — San Diego

06:0108:32
20 Aug 2026
4 h 31 m
Direct flight
AS
$ 121

Chicago — San Diego

06:0108:32
20 Aug 2026
4 h 31 m
Direct flight
AS
$ 121

Chicago — San Diego

06:0108:32
20 Aug 2026
4 h 31 m
Direct flight
AS
$ 121

Chicago — San Diego

14:1816:55
20 Aug 2026
4 h 37 m
Direct flight
AS
$ 121

Chicago — San Diego

06:0108:32
20 Aug 2026
4 h 31 m
Direct flight
AS
$ 121

Chicago — San Diego

14:2016:59
13 Aug 2026
4 h 39 m
Direct flight
AS
$ 121

Chicago — San Diego

06:2008:54
13 Aug 2026
4 h 34 m
Direct flight
AS
$ 121

Chicago — San Diego

06:2008:54
13 Aug 2026
4 h 34 m
Direct flight
AS
$ 121

Chicago — San Diego

06:2008:54
17 Aug 2026
4 h 34 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — San Jose flight

You can book flights from Chicago to San Jose directly on this page. The distance between the cities is approximately 2,964 km, and the flight frequency reaches about 6 flights per week.

Flights on this route are operated by United Airlines and Southwest Airlines. Ticket prices are dynamic, so to find the best deals, we recommend using the low-price calendar and checking information on how to get to the airport of departure and how to get from the airport to your destination.

Flight ticket prices by day: Chicago — San Jose

Below is a calendar of the lowest flight ticket prices for Chicago — San Jose by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $123 in ,, and the most expensive are around $182 in J. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → San Jose, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$242highMay$255highSep$191low
Feb$185lowJun$236mediumOct$172low
Mar$268highJul$223mediumNov$185low
Apr$230mediumAug$179lowDec$249high

Some values are estimated based on seasonality.

When to fly

The climate in San Jose features warm summers and mild winters. The hottest period is August, with an average maximum temperature of 28.3°C, while January is considered the rainiest and coolest month, seeing up to 98.43 mm of precipitation and lows of 6.8°C.

According to current data, the most budget-friendly flights are available in August, with prices starting $123. Currently, the most expensive month for booking is January, when ticket prices start $182.

August can be considered the ideal time for a trip: it is one of the driest months and offers the most attractive airfares. It is best to avoid the winter months if you want to minimize costs and the likelihood of rain.

Temperature · San Jose

Dry and wet days · San Jose

Wind speed and direction · San Jose

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How to get the best deal on a Chicago — San Jose ticket

  • Since the route is served by both the legacy carrier United Airlines and the major low-cost airline Southwest Airlines, be sure to check the baggage rules, as they can vary significantly.
  • Use the price trend chart on this page to determine which days of the week are cheaper to fly out of Chicago, as the difference can amount to several thousand rubles.
  • To secure the minimum fare starting $123, we recommend planning your trip for August and booking your tickets in advance.
  • If direct flights are unavailable or too expensive for your preferred dates, consider options with one short layover — this often helps you save money.

Airlines

Two airlines operate on the route between these cities, with United Airlines and Southwest Airlines being the primary carriers. Most flights are direct, providing a stable connection with a frequency of about 6 departures per week. You can view the detailed daily schedule and choose the best option in the interactive list below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → SJC5x/week
  • Southwest AirlinesWN
    2x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight MDW → SJC2x/week
      Duration
      4h 29m
      Days
      MTWTFSS

Cities and airports on the Chicago — San Jose route

Flights Chicago — San Jose depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Norman Y. Mineta San Jose International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure airports
Arrival airports

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Frequently asked questions about the Chicago — San Jose flight

How long is the flight from Chicago to San Jose?

The distance between the cities is 2,964 km. A direct flight usually takes about 3.5–4 hours, depending on weather conditions and the specific flight.

Which airlines serve this route?

Regular flights from Chicago to San Jose are operated by United Airlines and Southwest Airlines.

How much is the cheapest flight?

Ticket prices change constantly based on demand and season. You can find the current minimum for the near future in the low-price calendar on this page.

Which airport do flights arrive at?

Flights from Chicago land at San Jose International Airport (SJC), which is conveniently located near the city center and Silicon Valley sites.

Where else you can fly from Chicago

See all

Where else you can fly from San Jose

See all

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