Good to know - Cheap tickets San Jose — Chicago
| Cheapest flight found | $85 |
|---|---|
| Minimal flight time | 4h 5m |
| 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 |
|---|---|---|
| April 2026 | ||
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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 | |
|---|---|---|---|---|---|---|---|
| 06:30 | 12:55 | tue, wed, sat | UA2621 | United Express | 4h 25m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:05 | sun | WN3803 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 07:25 | 13:30 | sat | WN2409 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 14:10 | mon, thu, fri | WN2409 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 14:05 | mon, thu, fri | WN3803 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 14:45 | sat | WN3803 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:40 | 14:45 | sun | WN2409 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 15:30 | tue, wed | WN2409 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 10:40 | 16:50 | tue, wed | WN3803 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
Popular airlines flying San Jose — Chicago
Flight San Jose – Chicago is served by 15 airlines. 2 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Sales of tickets from San Jose to Chicago in the last 48 hours
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).
- Departure city: San Jose
- IATA code of the city of origin: SJC
- Departure airports: Norman Y. Mineta San Jose International Airport, Reid-Hillview
- Departure country: United States
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Destination country: United States
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 4h 5m.
LowCostClub always do a comparison of airfares San Jose — Chicago with several airlines (include United Express, Southwest Airlines). 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.
Most often, departures to Chicago are from San Francisco, this is the cheapest flight from $46. The nearest airports from San Jose with a flight to Chicago are located in Reno.
Popular International routes from San Jose
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
Are there any direct flights San Jose — Chicago?
Yes, they do: UA2621, WN3803, WN2409
Can we fly from San Jose to Chicago?
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. United Express, Southwest Airlines depart from San Jose on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Alaska Airlines, Allegiant Air, AlphaSky, American Airlines, Atlas Air, Delta Air Lines, FedEx, Frontier (Morrison the Crested Caracara Livery), Jet Linx Aviation, JSX, NetJets, Spirit Airlines, Sun Country Airlines, UPS, Volaris.
How long does it take to fly from San Jose to Chicago?
A direct flight lasts an average of 4h 5m, during which time the aircraft covers a distance of 2959 km.
How much do flights San Jose — Chicago cost?
The price of flights San Jose — Chicago starts from $85.
What days does the plane fly San Jose — Chicago?
Planes fly San Jose — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in San Jose and Chicago?
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.
What flights are currently flying from San Jose to Chicago?
The following flights fly between San Jose and Chicago: UA2621, WN3803, WN2409, WN2409, WN3803, WN3803, WN2409, WN2409, WN3803
What month is the cheapest to fly from San Jose to Chicago?
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.
Which airlines direct fly from San Jose to Chicago?
The following airlines have direct flights San Jose — Chicago: United Express, Southwest Airlines.
Which airlines fly from San Jose to Chicago?
All the following airlines flights San Jose — Chicago: Alaska Airlines, Allegiant Air, AlphaSky, American Airlines, Atlas Air, Delta Air Lines, FedEx, Frontier (Morrison the Crested Caracara Livery), Jet Linx Aviation, JSX, NetJets, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Express, UPS, Volaris.