Cheap flights San Jose — Chicago (SJC — CHI)

Good to know - Cheap tickets San Jose — Chicago

Cheapest flight found $85
Minimal flight time 3h 57m
Flight distance 2959 km
Most popular airline Southwest Airlines

Airfare San Jose – Chicago by month

Here you can find out in what months how much a ticket San Jose – Chicago costs to buy cheap plane tickets.

Month One-way Round-trip
September 2026
June 2026
May 2026
April 2026
March 2026
February 2026
January 2026
December 2025
November 2025
October 2025
September 2025
August 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights San Jose — Chicago

Departure Arrival Flight days Flight Airlines Flight time Airports
06:00 11:57 tue K9150 Kalitta Charters 3h 57m Norman Y. Mineta San Jose International Airport — Chicago Executive Airport Select dates
06:30 12:40 mon, thu, fri, sun WN2077 Southwest Airlines 4h 10m Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport Select dates
10:00 16:18 mon UA1485 United Express 4h 18m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
10:30 16:43 mon AA506 American Eagle 4h 13m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
10:35 16:45 sat WN2077 Southwest Airlines 4h 10m Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport Select dates
10:50 17:03 thu, fri AA506 American Eagle 4h 13m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
12:25 18:30 thu WN2077 Southwest Airlines 4h 5m Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport Select dates
14:25 20:39 mon, thu AA613 American Eagle 4h 14m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
16:20 22:38 sat UA2702 United Express 4h 18m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
17:40 23:58 fri UA1328 United Express 4h 18m Norman Y. Mineta San Jose International Airport — O'Hare International Airport Select dates
All routes

Sales of tickets from San Jose to Chicago in the last 48 hours

2026-04-28 one-way

2026-04-28 one-way

2026-05-11 - 2026-05-15

2026-05-15 - 2026-05-18

2026-05-17 - 2026-05-18

2026-05-15 - 2026-05-16

2026-02-14 - 2026-02-16

Dynamics airfare San Jose — Chicago by month for the last year

according to LowCost.Club for the last year

The airfare depends on the departure date. Our chart shows the low season prices on route San Jose — Chicago

The graph shows that booking flights San Jose — Chicago is best planned for February and flights San Jose — Chicago — San Jose in the month of April.

Flights San Jose — Chicago

The selection of cheap flights San Jose — Chicago

Here you can find and purchase the cheapest flights San Jose — Chicago from $85 and San Jose — Chicago — San Jose from $84.

The price of the flight San Jose — Chicago (United States) — San Jose from $84 (round-trip).

The average price of the flight San Jose — Chicago (United States) — San Jose $363 (round-trip).

Low cost flights San Jose — Chicago (SJC — CHI)

The distance between San Jose and Chicago 1839 miles (or 2959 kilometres).

The time difference between San Jose and Chicago is 2 h.

Minimal flight time from San Jose to Chicago 3h 57m.

LowCostClub always do a comparison of airfares San Jose — Chicago with several airlines (include Kalitta Charters, Southwest Airlines, United Express). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets San Jose — Chicago. Last week, for instance, the cheapest round-trip prices stood at $84 while the cheapest one-way price that was available within the last week cost $85

Routes from nearby cities to Chicago

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to Chicago is from Oakland. The cheapest airfare can be purchased with a flight from San Francisco from $46. The nearest airports from San Jose with a flight to Chicago are in Reno.

Popular International routes from San Jose

San Jose — Coimbatore

San Jose — Calama

San Jose — Cairns

Popular routes from Chicago

If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:

Popular domestic routes from San Jose

FAQ about San Jose — Chicago

Yes, they do: K9150, WN2077, UA1485, AA506, AA613, UA2702, UA1328, UA1704

Yes, you can fly from San Jose to Chicago. San Jose has 2 airports (Norman Y. Mineta San Jose International Airport, Reid-Hillview) for flights. Kalitta Charters, Southwest Airlines, United Express, American Eagle depart from San Jose on mon, tue, thu, fri, sat, sun. There are non-direct flights through Alaska Airlines, Allegiant Air, AlphaSky, Atlas Air, Breeze Airways, Delta Air Lines, FedEx, Frontier (Luis the Axolotl Livery), Jet Linx Aviation, NetJets, SkyWest Airlines, Slate Aviation, Sun Country Airlines, Volaris.

A direct flight lasts an average of 3h 57m, during which time the aircraft covers a distance of 2959 km.

The price of flights San Jose — Chicago starts from $85.

Planes fly San Jose — Chicago 6 times a week on the following days: mon, tue, thu, fri, sat, sun

In San Jose — Norman Y. Mineta San Jose International Airport, Reid-Hillview. In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport.

The following flights fly between San Jose and Chicago: K9150, WN2077, UA1485, AA506, WN2077, AA506, WN2077, AA613, UA2702, UA1328, UA1328, UA1704

High season is considered to be April and the cheapest month is February. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest San Jose — Chicago flight deals.

The following airlines have direct flights San Jose — Chicago: Kalitta Charters, Southwest Airlines, United Express, American Eagle.

All the following airlines flights San Jose — Chicago: Alaska Airlines, Allegiant Air, AlphaSky, American Eagle, Atlas Air, Breeze Airways, Delta Air Lines, FedEx, Frontier (Luis the Axolotl Livery), Jet Linx Aviation, Kalitta Charters, NetJets, SkyWest Airlines, Slate Aviation, Southwest Airlines, Sun Country Airlines, United Express, Volaris.

Low price calendar

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