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Selected fares from Oakland to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Route Information for Flights from Oakland to Chicago
| Origin Airport IATA Code | SFO |
|---|---|
| Destination Airport IATA Code | MDW |
| Flight Price | $86 |
| Distance | 2,962 km |
Oakland (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 perfect page to snatch a killer rate on your upcoming flight from Oakland. Whether you call yourself an expert at navigating the friendly skies or only have a few trips under your wing, read below to score the best deal on your next flight.
How can you get a great rate on tickets from Oakland to Chicago?
We've been doing this for years, so we know a couple ways to snag the best deal on your flight to Chicago. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.
Which days of the week are cheapest to fly?
Going with the flow can pay dividends when it comes to getting an affordable flight. Tuesday and Wednesday typically have the best rates. Next in line are Thursday and, surprisingly, Saturday. Most like to fly back from their trip on Sunday so you can save by leaving a day earlier.
Why are flights cheaper if you stay over the weekend?
Spending the weekend at your destination, like Chicago, usually means a more affordable return ticket since most people fly during this time. We are all for that!
Why travel during the off-peak season?
Off-peak and shoulder seasons are when most vacationers aren't flying to certain locations. So when it is cold, most people head off to warmer places like the Caribbean, Mexico, Hawaii, etc., just like our feathered friends. But in the summer, you'll find that Europe gets busy. You can usually save on your ticket when you fly when everyone else isn't.
Jump on that great rate
You're not the only one searching for a terrific deal on a ticket from Oakland to Chicago. You may miss your opportunity to get the flight and the schedule you like.
What is the Hotwire Hot Rate?
If you prioritize cost over everything else, then the Hotwire Hot Rate is for you. You can get one of the best rates on your ticket to Chicago from Oakland. You won't know the time and airline until after you book, but it is a risk where you can reap the rewards.
Book your Oakland to Chicago flight today
We're here to help you save some money on your ticket to Chicago. These tips can help you land that unreal deal. For the ultra-flexible-go with the flow vacationer, go for the Hotwire Hot Rate. You'll get your flight and have more money in your pockets to do Chicago the way you want. So say "So long" to Oakland and "What's up?" to Chicago.
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^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.