Cheap flights from Chicago to San Jose

Chicago FSS
CHI
Norman Y. Mineta
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 22 September, from $91.

Top 10 cheap flights from Chicago to San Jose

DL
DL
DL
$ 133

Chicago — San Jose

06:35—17:38
8 Oct 2026
13 h 3 m
2 stops
DL
DL
DL
$ 133

Chicago — San Jose

06:35—19:52
8 Oct 2026
15 h 17 m
2 stops
DL
DL
DL
$ 133

Chicago — San Jose

06:35—17:38
7 Oct 2026
13 h 3 m
2 stops
DL
DL
DL
$ 133

Chicago — San Jose

06:35—19:52
7 Oct 2026
15 h 17 m
2 stops
DL
DL
DL
$ 133

Chicago — San Jose

07:00—17:24
3 Oct 2026
12 h 24 m
2 stops
DL
DL
DL
$ 133

Chicago — San Jose

07:00—19:51
3 Oct 2026
14 h 51 m
2 stops
AS
AS
$ 133

Chicago — San Francisco

15:49—21:49
6 Oct 2026
8 h
1 stop
AS
AS
$ 133

Chicago — San Jose

07:00—13:18
6 Oct 2026
8 h 18 m
1 stop
AS
AS
$ 133

Chicago — San Francisco

15:49—22:49
6 Oct 2026
9 h
1 stop
AS
AS
$ 133

Chicago — San Francisco

09:00—16:08
6 Oct 2026
9 h 8 m
1 stop

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

About the Chicago — San Jose flight

Looking for cheap flights from Chicago to San Jose? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — San Jose ticket online at the best price.

The route has direct flights — around 19 flights per week, flights are operated by United Airlines, Southwest Airlines, a nonstop flight takes about 4 h 36 min, the distance between the cities is around 2,964 km.

Planning your trip? You may find our San Jose travel guide, how to get from the airport into town and San Jose weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $91Min. price
SeptemberCheapest
JanuaryPeak season
YesDirect flights
2,964 kmDistance
4 h 36 minTravel time
2Airlines
19 / wkFlights

Flight schedule from Chicago to San Jose

The table shows direct flights from Chicago to San Jose on the selected date. The flight takes approximately 4 h 36 min. Regular flights are operated by United Airlines and Southwest Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Norman Y. Mineta San Jose International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 08 Sep 2026

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 $91 in September, and the most expensive are around $166 in January. 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

Average one-way fares from Chicago to San Jose by month. Tickets are usually cheapest in October (around $157) and priciest in March (about $245) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$221highMay$233highSep$175low
Feb$169lowJun$216mediumOct$157low
Mar$245highJul$204mediumNov$169low
Apr$210mediumAug$163lowDec$227high

Some values are estimated based on seasonality.

When to fly

Weather in San Jose: it is warmest in August (up to 28 °C on average) and coolest in January (around 15 °C). The driest month is June.

Tickets are usually cheapest in September and most expensive in January. Compare prices and weather by month in the charts below to pick the best time to fly.

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

  • Book ahead: fares for Chicago — San Jose are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to San Jose is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — San Jose route are operated by 2 airlines; United Airlines runs the most flights (around 74% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → SJC5x/week
      Duration
      4h 46m
      Days
      MTWTFSS
    73.7%Open →
  • Southwest AirlinesWN
    2x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight MDW → SJC2x/week
      Duration
      4h 28m
      Days
      MTWTFSS
    26.3%Open →

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

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

San Jose

SJC
United States
About the cityHow to get thereWeatherAll about the country United States
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?

A nonstop Chicago — San Jose flight takes about 4 h 36 min — the distance between the cities is around 2,964 km.

How far is it from Chicago to San Jose?

The distance from Chicago to San Jose is about 2,964 km, which a nonstop flight covers in around 4 h 36 min.

Are there direct flights from Chicago to San Jose?

Yes, there are nonstop flights Chicago — San Jose — around 19 flights per week.

Which airlines fly from Chicago to San Jose?

Airlines operating Chicago — San Jose include United Airlines, Southwest Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — San Jose flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Norman Y. Mineta San Jose International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to San Jose?

The price of a Chicago — San Jose ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in January. Tickets typically cost between $91 and $166. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — San Jose?

Flights Chicago — San Jose are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to San Jose?

To catch a low fare Chicago — San Jose, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from San Jose

See all
SeattleSan DiegoLos AngelesPortlandLas VegasDenverGuadalajaraDallasSalt Lake CityPhoenixHonoluluAtlantaSan Jose del CaboBoiseKahuluiKailua-KonaKapaaMinneapolisDetroitPuerto VallartaMoreliaHoustonLeonTokyoZacatecasNew York CityMexico CityLondonMiamiTorontoParisLimaSao Paulo

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