Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Selected fares from Silicon Valley to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Route Information for Flights from Silicon Valley to Chicago
| Origin Airport IATA Code | OAK |
|---|---|
| Destination Airport IATA Code | ORD |
| Flight Price | $194 |
| Distance | 2,929 km |
Silicon Valley (SJC) to Chicago (CHI)
Are you flying to Chicago for a much-needed vacation or is it about time for you to have a family reunion? Or maybe you're traveling for work? Hey, anything that gets you away from that desk is a win in our books. You're on the right page to score an awesome rate on your upcoming flight from Silicon Valley. Whether you call yourself an expert at navigating the friendly skies or aerial amateur, read on to see how to book a too-good-to-be-true flight.
How do you get the best deal on a flight from SJC to CHI?
We've been doing this for years, which means getting that great deal on a Chicago flight is easy-peasy. You'll make spending less look so very good with a few simple tips and tricks.
What is the cheapest day to fly?
With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:
- Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. Most people opt to depart at the beginning or end of the week.
- Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your vacay by a day and increase your savings.
- Monday through Thursday—If you're flying internationally, deals are often available when departing these days.
What's the Saturday night stay rule?
Staying the weekend at your destination, like Chicago, usually means lower airfare since most people fly during this time. Good thing to tell your boss if you have a business trip -- wink-wink.
What are shoulder seasons?
Shoulder or off-peak seasons are when most people aren't traveling to certain locations. So when it is chilly, most people head to warmer climates like the Caribbean, Mexico, Hawaii, etc., just like the birds (they had it figured out). But during the summer months, you'll find that Europe is where it's at. You can usually save on your flight when you fly when everyone else isn't.
If the price is right, pick it!
Airline carriers change their rates often. If a price you like pops up, then get it! Unsurprisingly, you're not the only person searching for a great bargain on a ticket from Silicon Valley to Chicago. You may miss out on your opportunity to dial in the time and the flight you wanted.
Are there any other ways to save on my flight to Chicago?
The Hotwire Hot Rate is what makes Hotwire one of the best bargains out there. You'll get one of the best rates on your flight from Silicon Valley (SJC) to Chicago (CHI). You won't find out the time and airline until after you book, but with a little risk you can get huge savings.
Book your flight today
We're here to help you save some money on your next flight from Silicon Valley to Chicago. Use our guide to get you that oh-so-nice price. And if you are feeling lucky (and you always will be) book the Hotwire Hot Rate for unbelievable savings. So say "So long" to Silicon Valley and "What's up?" to Chicago.
More to explore for Silicon Valley to Chicago
Explore Chicago with Hotwire's Travel Guides to find the best flights, cars, vacation packages and more!
Other Flights from Silicon Valley
- Silicon Valley to Los Angeles
- Silicon Valley to Washington
- Silicon Valley to San Antonio
- Silicon Valley to Salt Lake City
- Silicon Valley to Denver
- Silicon Valley to Guadalajara
- Silicon Valley to Dallas
- Silicon Valley to Nashville
- Silicon Valley to Baltimore
- Silicon Valley to Pittsburgh
- Silicon Valley to Boise
- Silicon Valley to Indianapolis
Flights to Cities near Silicon Valley
Flights to Cities near Chicago
^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 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.