$44 Cheap flight deals from Silicon Valley (SJC) to Chicago (CHI)

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This Weekend's Flight Deals from Silicon Valley to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $44 One Way, $119 Round Trip from Silicon Valley to Chicago

Prices starting at $119 for return flights and $44 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago economy flight packages

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Chicago Marriott Downtown Magnificent Mile
LondonHouse Chicago, Curio Collection by Hilton
DoubleTree by Hilton Chicago - Magnificent Mile
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More About Flying To Chicago from Silicon Valley

Route Information for Flights from Silicon Valley to Chicago

Origin Airport IATA Code
SJC
Destination Airport IATA Code
CHI
Distance
1842 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Aer Lingus, Emirates, Virgin Australia, Asiana Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, China Southern Airlines, Finnair, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Air China, Gulf Air, British Airways
Earliest Flight Arrival
1:30PM UTC
Latest Flight Arrival
1:20PM UTC

Plan Your Trip from San Jose to Chicago

San Jose, CA, Airport Information

San Jose, CA, is home to nearly one million people, a large city population that's serviced by its own international airport, providing regular flights from San Jose to international and domestic destinations. The Norman Y. Mineta Memorial San Jose International Airport is only two miles from the downtown area at the intersections of U.S. Route 101, Interstate 880 and State Route 87. The primary airlines operating from the airport are Southwest Airlines and Alaska Airlines. Reservations for you airline ticket on these or other airlines serving the airport can be made through Orbitz.com.

Parking at the Airport

Parking at Mineta San Jose International Airport is available at three hourly and three daily lots, one of which offers economy service. The hourly lots are interspersed around the terminal area for easy access, costing $2 for 30 minutes and $30 per day flat rates. The daily lots offer parking deals with discounted parking fees of $22 a day for the regular daily lots and $15 for the economy lot, which is further away from the terminals. Disabled parking is available in front of both terminals for a $2 rate for 30 minutes and $15 for a daily charge.

Transportation From the Airport

Several methods of travel are available for passengers to make their way from anywhere in the city to the airport. Several hotels in the area offer courtesy shuttle transportation for patrons. Public bus transportation is available from the Valley Transportation Authority, and metered taxi service is also available from anywhere in the area, with the downtown-to-airport fare costing approximately $15 to $18.

Breakfast Before Departing

A quick meal can be eaten at the airport before departure in one of the many restaurants available in the concourse. Only ticketed passengers are allowed in the area containing the restaurants. Coffee and pastries are served at the Euro Café near the baggage claim area, while Starbucks can provide sandwiches as well, to get you quickly to the available flights from San Jose. If you have a bit more time to stop off on the way to the airport, try a sit-down breakfast at Café San Jose on Meridian Ave. or at Bill's Cafe on Willow St.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Silicon Valley to Chicago?
Yes, if you’re cruising from SFO to Chicago, IL (ORD-O’Hare Intl.), you’ll only have one flight number to remember. There are 3 airlines that offer nonstop services to choose from. Some of the best are:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Silicon Valley to Chicago?
With the flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Airport taking a minimum of 4 hours and 40 minutes, there’s plenty of time to kick back and enjoy the experience. Treat yourself to a glass of red and settle into your seat with an absorbing movie or novel.
What airlines fly from Silicon Valley to Chicago most frequently?
The carriers that offer the most frequent flights between San Francisco, CA (SFO-San Francisco Intl.) and O’Hare Airport include United Airlines (UA). This well-known option operates 243 flights on the route each month. American Airlines (AA) also flies from Silicon Valley to Chicago. It’s another great option and has 126 flights monthly.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.