Private charter · SJC → MDW
San Jose to Chicago
1,833 miles. One price for the whole airplane.
Price your flight from San Jose to Chicago
The trip
San Jose to Chicago, door to door faster.
Trade about 38½ hours on the road for about a short flight in the air. Bluebird flies you direct from Mineta San Jose International Airport in San Jose to Chicago Midway International Airport in Chicago, 1,833 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 1,833 mi
- Flight
- —
- Driving
- 38½ hours
- Passengers
- Up to 1
Departing San Jose
Airports in San Jose
SJC
Major airportMineta San Jose International Airport
San Jose · KSJC
- From downtown
- 3 mi
- Longest runway
- 11,000 ft
NUQ
Commercial airportMoffett Federal Airfield
Mountain View · KNUQ
- From downtown
- 10 mi
- Longest runway
- 9,197 ft
LVK
Regional airportLivermore Municipal Airport
Livermore · KLVK
- From downtown
- 25 mi
- Longest runway
- 5,253 ft
HWD
Regional airportHayward Executive Airport
Hayward · KHWD
- From downtown
- 26 mi
- Longest runway
- 5,694 ft
Arriving Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
When you land
Things to do in Chicago
Chicago is the commercial center of the Midwest, a city where commodity and futures trading, banking, law, consulting, logistics and corporate headquarters share a skyline that helped invent the skyscraper. CME Group’s exchanges, the offices along LaSalle Street, the medical and research campuses of Northwestern and the University of Chicago and a long roster of Fortune 500 companies keep executives moving in and out every day, while the Loop, River North and the Magnificent Mile pull in shoppers, conventioneers and theatergoers year-round.
- 01
Art Institute of Chicago
One of the great encyclopedic museums in the world, with celebrated Impressionist paintings, Grant Wood’s American Gothic, Hopper’s Nighthawks and the light-filled Modern Wing facing Millennium Park.
- 02
Millennium Park
Anish Kapoor’s mirrored Cloud Gate, the Crown Fountain and Frank Gehry’s Jay Pritzker Pavilion, which hosts free summer concerts, make this downtown park the city’s favorite gathering place.
- 03
Chicago Architecture Center River Cruise
Docent-led boat tours glide along the Chicago River past more than a century of landmark towers, explaining how the city rebuilt itself after the Great Fire of 1871.
- 04
Wrigley Field
Home of the Cubs since 1916, the ivy-covered ballpark in Lakeview is surrounded by rooftop seating and neighborhood bars, and stadium tours run on many non-game days.
- 05
Field Museum
On the lakefront Museum Campus, this natural history museum is home to SUE, one of the largest and most complete Tyrannosaurus rex skeletons ever found, along with ancient Egypt and gem halls.
- 06
Lincoln Park Zoo
One of the oldest zoos in North America and free to visit, set among lagoons, gardens and the historic Lincoln Park Conservatory just north of downtown.
Questions
San Jose to Chicago flights
How long is a private flight from San Jose to Chicago?
About a short flight in a private jet, for 1,833 miles direct. Driving the same trip takes about 38½ hours.
Which airports do flights from San Jose to Chicago use?
You can depart from Mineta San Jose International Airport (SJC), Moffett Federal Airfield (NUQ), or Livermore Municipal Airport (LVK) and arrive at Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from San Jose to Chicago cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between San Jose and Chicago?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Chicago back to San Jose are priced the same way.
Return flight
Chicago to San Jose
More flights from San Jose
More flights to Chicago
Explore San Jose private charter and Chicago private charter, airports and things to do. Arriving at Chicago Midway International Airport (MDW).
San Jose to Chicago, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
Get an instant price