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Fares from $27 One Way, $115 Round Trip from Silicon Valley to Chicago

Prices starting at $115 for return flights and $27 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.

Need A Hotel In Chicago?

Hotels In Top Chicago Neighborhoods

Near North Side
259 hotels

Loews Chicago Hotel

4.5 out of 5.0
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$179

South Loop
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Congress Plaza Hotel

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Stay Near Exciting Chicago Attractions

More About Flying To Chicago from Silicon Valley

Flights from Silicon Valley to Chicago - Frequently Asked Questions

Are there non-stop flights from Silicon Valley to Chicago?

You'll find 3 airlines that offer direct services from San Francisco, CA (SFO-San Francisco Intl.) to Chicago, IL (ORD-O'Hare Intl.), so get ready to hit that "book" button. One of these carriers will have the flight you're looking for:

  • United Airlines
  • American Airlines
  • Alaska Airlines
What is the shortest flight from Silicon Valley to Chicago?

The shortest flight from San Francisco, CA (SFO-San Francisco Intl.) to Chicago, IL (ORD-O'Hare Intl.) is 3 hours and 57 minutes. Slip a few things into your carry-on to stop you from getting bored, like an interesting read or some Sudoku puzzles.

What airlines have the most flights from Silicon Valley to Chicago?

There are two airlines offering frequent flights from San Francisco, CA (SFO-San Francisco Intl.) to Chicago, IL (ORD-O'Hare Intl.), including United Airlines (UA). A top pick for many travelers, it operates 322 flights on this route every month. American Airlines (AA) will also take you to your destination in comfort and style. Offering 146 flights per month between Silicon Valley and Chicago, it's another popular airline to look into.

Route Information for Flights from Silicon Valley to Chicago

Origin Airport IATA CodeSJC
Destination Airport IATA CodeCHI
Distance1842 mi
Direct Flight AirlinesAmerican Airlines, Air Canada, LOT - Polish Airlines, Aer Lingus, Air New Zealand, United Airlines, Alaska Airlines, Qantas, SAS, Royal Jordanian, Air China LTD, Singapore Airlines, British Airways
Earliest Flight Arrival8:19PM UTC
Latest Flight Arrival12:06PM UTC

Flights Review

Aug 18, 2019

The flight attendants really helped my husband and I the ladies in the back of the plane were wonderful. My husband has a tumor in his spine we used your wheelchair service everyone was awesome to us. We are now here at Mayo in Rochester. Thank to all your crew from SJC to Rochester Minn

Aug 13, 2019

Too expensive!

Aug 11, 2019

Good experience

Jul 12, 2019

Good customer service

Jul 22, 2018

Seat spacing is so tight my knees are constantly jammed into the seat ahead of me. Tall is a handicap at Times.

Jun 12, 2018

Very long line to drop off bag.

May 29, 2018

Serving extra water is a great idea.

Feb 2, 2018

Great seats! Seemed very roomy in coach class.

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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.