⚡ Fare recorded April 25, 2026 · Prices change daily

San Jose to Chicago flights

San Jose (SJC) to Chicago (CHI): 1,825 miles (2,937 km) great-circle, about 4h 10m nonstop by our estimate. Cheapest fare observed: $261 round-trip on Southwest, nonstop, departing May 22, 2026.

WNSouthwestWN4252
Depart
SJC
San Jose, USA
22:55
2026-05-22
✈
Arrive
CHI
Chicago, United States
Returns 21:50
2026-05-25
Stops
non-stop
Distance
1,825 mi
Est. nonstop time
4h 10m
Trip type
Round-trip
$261
Round-trip · per person
Book this flight →
Also compare on Aviasales →
About this flight

When did the cheapest San Jose to Chicago fare fly?

$261 round-trip, Southwest WN4252, departing 2026-05-22 at 22:55, returning 2026-05-25. The recorded itinerary left on a Friday, returning on a Monday 3 nights later; the fare was observed 27 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.

Route facts

How far is San Jose from Chicago?

  • Distance: 1,825 miles (2,937 km) great-circle, heading east (measured to Chicago O'Hare International Airport, ORD).
  • Estimated nonstop flight time: about 4h 10m.
  • Departure airport: Mineta San Jose International Airport (SJC), San Jose, United States, UTC-7 on May 22, 2026.
  • Arrival: Chicago (CHI, all airports), United States, UTC-5 on May 22, 2026.
  • Time difference: Chicago is 2 hours ahead of San Jose on the recorded date.
  • Route type: domestic, within United States.
  • Recorded itinerary: Southwest WN4252, non-stop, round-trip, 3 days between departure and return.
Fare comparison

How does the San Jose to Chicago fare compare with other routes from SJC?

At $261, it ranked 7th of the 30 round-trip fares we recorded from SJC (median $415). That is 14.3 cents per great-circle mile (round-trip price over one-way distance), below the SJC median of 23.1 cents across 30 round-trip routes.

Routes from SJC of similar length: Mexico City (1,852 mi) at $552 and Indianapolis (1,920 mi) at $448.

Southwest had the cheapest fare on 7 of 30 SJC routes. It is the 20th longest of the 30 routes we track from SJC.

Other ways in

What did other cities pay to fly to Chicago?

Of 33 departure airports with a fare to Chicago, San Jose (SJC) ranked 22nd at $261. Lowest: $89 from Atlanta (ATL); highest: $1241 from Nairobi (NBO); 16 nonstop. Cheapest-fare airlines (routes): Frontier (15), Spirit (5), United Airlines (4), American Airlines (2), airline 0O (1) and Alaska Airlines (1), plus 5 more.

Sources

Where do these numbers come from?

Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Los_Angeles, America/Chicago; flight time is our estimate.

FAQ

San Jose to Chicago flight questions

How far is San Jose from Chicago by plane?

+
San Jose is about 1,825 miles (2,937 km) from Chicago on a great-circle line from Mineta San Jose International Airport (SJC) to Chicago O'Hare International Airport (ORD), heading east. CHI is the city code that covers every commercial airport in Chicago; distances on this page are measured to Chicago O'Hare International Airport (ORD). It is the 20th longest of the 30 routes we track from SJC. The recorded itinerary was nonstop.

How long is the flight from San Jose to Chicago?

+
About 4h 10m nonstop by our estimate for 1,825 miles (500 mph cruise plus 30 minutes, not a timetable). The recorded Southwest fare was nonstop. 33 airports in our feed had a fare to Chicago; this one ranked 22nd, and 16 of the 33 were nonstop.

What is the time difference between San Jose and Chicago?

+
On May 22, 2026, San Jose was on UTC-7 (America/Los_Angeles) and Chicago on UTC-5 (America/Chicago), so Chicago was 2 hours ahead of San Jose: noon in San Jose was 14:00 in Chicago. Both zones shift for daylight saving together, so the gap stays the same in January and July.

How much is a flight from San Jose to Chicago?

+
As observed on April 25, 2026: $261 per person round-trip on Southwest flight WN4252, departing May 22, 2026, returning May 25, 2026, nonstop. At $261, it ranked 7th of the 30 round-trip fares we recorded from SJC (median $415). That is 14.3 cents per great-circle mile (round-trip price over one-way distance), below the SJC median of 23.1 cents across 30 round-trip routes. Prices change daily, so check the live fare.

Is there a nonstop flight from San Jose to Chicago?

+
Yes, the cheapest recorded fare was a nonstop Southwest flight, WN4252, on May 22, 2026. Into Chicago, 16 of the 33 recorded fares were nonstop. From SJC, 10 of 30 were. Routes from SJC of similar length: Mexico City (1,852 mi) at $552 and Indianapolis (1,920 mi) at $448.

Which airports serve flights from San Jose to Chicago?

+
It departs Mineta San Jose International Airport (SJC) in San Jose, United States, and arrives at Chicago (CHI) in Chicago, United States. CHI is the city code that covers every commercial airport in Chicago; distances on this page are measured to Chicago O'Hare International Airport (ORD). A domestic United States flight.

Where else near Chicago can you fly from San Jose?

Indianapolis (IND) $448Washington (WAS) $349Atlanta (ATL) $427Philadelphia (PHL) $364New York (NYC) $421Denver (DEN) $245All flights from San Jose →

Other cities with flights to Chicago

From Atlanta (ATL) $89From Dallas (DFW) $94From Houston (IAH) $101From Fort Lauderdale (FLL) $126From Los Angeles (LAX) $126From Newark (EWR) $156

Ready to fly?

Book Southwest SJC → CHI · $261 →