Skyscanner home

Cheap Flights from Chicago to Oakland Metropolitan Oak

Compare Chicago to Oakland Metropolitan Oak flight deals

Find the cheapest month or even day of the year to fly to Oakland Metropolitan Oak

Book the best Oakland Metropolitan Oak fare with no extra fees

Flight deals from Chicago to Oakland Metropolitan Oak

Looking for a cheap last-minute deal or the best return flight from Chicago to Oakland Metropolitan Oak Airport? If you want to travel next month, return fares start from R 4,298. Find the lowest prices on one-way and return tickets right here.
Oakland.R 1,743 per passenger.Departing Wed, 16 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 16 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,743, select.
Oakland.R 2,069 per passenger.Departing Tue, 18 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 18 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,069, select.
Oakland.R 2,076 per passenger.Departing Wed, 22 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 22 Jul, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,076, select.
Oakland.R 2,237 per passenger.Departing Tue, 30 Jun.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 30 Jun, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,237, select.
Oakland.R 2,363 per passenger.Departing Sat, 24 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,363, select.
Oakland.R 2,743 per passenger.Departing Mon, 26 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 26 Oct, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,743, select.
Oakland.R 2,911 per passenger.Departing Mon, 4 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 4 Jan, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,911, select.
Oakland.R 3,182 per passenger.Departing Fri, 4 Dec.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Fri, 4 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 3,182, select.
Oakland.R 3,491 per passenger.Departing Thu, 25 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 25 Jun, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 3,491, select.
Oakland.R 5,824 per passenger.Departing Mon, 30 Nov.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 30 Nov, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 5,824, select.
Oakland.R 7,904 per passenger.Departing Mon, 30 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 30 Nov, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 7,904, select.

Find the cheapest month to fly from Chicago to Oakland Metropolitan Oak

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Oakland Metropolitan Oak flights are currently cheapest in September.
Jun
from R 2,237
Jul
from R 2,076
Aug
from R 2,069
Sep
from R 1,743
Oct
from R 2,363
Nov
from R 5,824
Dec
from R 3,182
Jan
from R 2,911
Feb
Find prices
Mar
Find prices
Apr
Find prices
May
Find prices

Direct flights from Chicago to Oakland Metropolitan Oak

Chicago to Oakland Metropolitan Oak: Alternative routes

Compare routes from Chicago to Oakland below. You may find an airport to fly into that's cheaper, faster, or easier than Oakland Metropolitan Oak.

Oakland Metropolitan Oak

10km from central Oakland
ClosestCheapest
from R 1,743
Search flights

San Francisco International

23km from central Oakland
from R 1,802
Search flights

Concord

28km from central Oakland
Search flights

San Carlos

32km from central Oakland
Search flights

San Jose International

58km from central Oakland
from R 1,933
Search flights

San Jose Reid-Hillview

66km from central Oakland
Search flights

Chicago to Oakland: Flight information

The things to know before you go.
Cheapest flight foundR 1,743
Cheapest month to flySeptember
Average flight time4 hrs, 37 mins
Most popular airlineSouthwest Airlines
Average flights per week16

Finding cheap flights from Chicago to Oakland Metropolitan Oak: Frequently asked questions

The best price we found for a return flight from Chicago to Oakland Metropolitan Oak is R 3,486. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 37 minutes is the average flight time from Chicago to Oakland Metropolitan Oak.
Southwest Airlines flies direct from Chicago to Oakland Metropolitan Oak.
As of June 2026, there are 16 flights per week flying from Chicago to Oakland Metropolitan Oak.
The cheapest month to fly from Chicago to Oakland Metropolitan Oak is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Oakland Metropolitan Oak Airport on Wednesday, 16 September 2026.
Yes – the average flight time is 4 hours and 37 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Oakland Metropolitan Oak but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Oakland is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Oakland Metropolitan Oak is Southwest Airlines .

Flying from Chicago to San Francisco Bay Oakland International Airport (OAK): What you need to know

  • Start your adventure at Chicago Midway International Airport (MDW), the main airport in Chicago. Search for flights from Chicago to San Francisco Bay Oakland International Airport (OAK) that leave from this terminal.

  • Oakland is two hours behind Chicago. San Francisco Bay Oakland International Airport is located in Oakland, which operates on the UTC-8 timezone.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Make sure you're at the airport on time to catch your flight from Chicago to OAK.

  • Peak months like July or holiday periods such as Thanksgiving and Christmas will mean longer lines at check-in and security. If you're travelling then, play it safe and head to the terminal even earlier. Arriving two hours before a domestic flight and up four hours ahead of international flights is wise.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Located around 27 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car (depending on traffic). The journey by public transport will take roughly 45 minutes.

  • Looking for a comfortable hotel near Chicago O'Hare International Airport? If you've booked an early flight from Chicago to San Francisco Bay Oakland International Airport, these accommodation options will put you conveniently close to check-in:

  • Of the departures from Chicago O'Hare International Airport, 70% touch down on time at their destination.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Looking to fly out of Chicago Midway International Airport (MDW)? Direct Chicago to San Francisco Bay Oakland International Airport (OAK) plane tickets are available from this popular hub.

  • From MDW, direct flights from Chicago to OAK can be booked with Southwest Airlines.

  • Southwest Airlines has the largest share of bookings on the MDW to OAK route.

  • Among the carriers operating flights between Chicago Midway International Airport and San Francisco Bay Oakland International Airport, Southwest Airlines leads in on-time performance.

  • You can arrive at MDW from the centre of Chicago in approximately 25 minutes by car, depending on traffic conditions. The journey on public transport takes roughly 30 minutes to travel the 16 kilometres or so.

  • Got an early start? You might like to check in to one of these accommodation options near Chicago Midway International Airport the day before your Chicago to OAK flight:

  • When it comes to flight punctuality, Chicago Midway International Airport has an on-time arrival performance of 76%.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The trip to RFD from central Chicago is around 2 hours by public transport. If you're planning to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.

  • Stay in bed a little longer and still make your Chicago to San Francisco Bay Oakland International Airport flight with plenty of time to spare. These hotels near Chicago Rockford International Airport make getting to the terminal a breeze if you're flying out early:

  • Flights that take off from RFD make it to their destination within the scheduled time frame 71% of the time.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About San Francisco Bay Oakland International Airport (OAK)

  • Have a late flight from Chicago to San Francisco Bay Oakland International Airport? Don't let it leave you bleary-eyed. Check in to one of these hotels near OAK and get cosy, quick:

  • For the best deal, book your vehicle around one week ahead of your Chicago to San Francisco Bay Oakland International Airport flight.

  • The street address for OAK is 1 Airport Drive.

Getting from San Francisco Bay Oakland International Airport (OAK) to central Oakland

  • Central Oakland is around 11 kilometres from San Francisco Bay Oakland International Airport and takes about 20 minutes to reach by car. See what your options are for making the trip into the city, whether that's with a taxi, car hire or ride-share.

  • It typically takes 30 minutes to get there using public transport.

How to find the cheapest flights from Chicago to San Francisco Bay Oakland International Airport (OAK)

  • R 1,743 is the lowest price for a one-way ticket from Chicago to San Francisco Bay Oakland International Airport. A return flight starts from R 3,486. These prices may change based on availability.

  • Booking early is often the key to finding a cheap flight from Chicago to OAK. Prices tend to rise as demand increases, so the closer you get to departure, the more you'll likely spend on your ticket.

  • The 'Whole month' search tool will show you the cheapest Chicago to San Francisco Bay Oakland International Airport tickets across every month. It's an easy way to find a bargain if your trip dates are flexible.

  • You don't need to search every day to find out if prices have dropped when you create a Price Alert. We'll let you know the moment there's a better deal on plane tickets from Chicago to OAK.

  • Tailor your trip using filters. Select your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Chicago to San Francisco Bay Oakland International Airport.

The best time to fly from Chicago to San Francisco Bay Oakland International Airport (OAK)

  • December is the quietest month for flights from Chicago to San Francisco Bay Oakland International Airport (OAK), while July is the busiest. Pick the best time to visit Oakland based on whether you want a bustling atmosphere or a more laid-back vibe.

  • When booking your Chicago to OAK plane ticket, consider what kind of weather works for you. September is the warmest month in Oakland, with temperatures ranging from 12ºC (54ºF) to 26ºC (79ºF).

  • If you want to travel in cooler conditions, search for a cheap ticket from Chicago to San Francisco Bay Oakland International Airport in January when temperatures are between 4ºC (39ºF) and 17ºC (63ºF).

More about Oakland

  • After booking your flight from Chicago to San Francisco Bay Oakland International Airport, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Oakland:

  • There are so many things to see and do in this city, it can be tricky to know where to begin. Fox Theatre, African American Museum and Library and Oracle Arena are top attractions which should be on any well-planned Oakland itinerary.

Explore more of the United States

  • Oakland is easy to fall in love with, but there are so many other corners of the United States waiting to be explored. About 241 kilometres southeast of Oakland, a visit to Fresno will keep your itinerary packed. Start with attractions like Forestiere Underground Gardens, Shinzen Japanese Garden and Fresno Chaffee Zoo.

  • Sacramento is another standout destination in the United States and is around 113 kilometres northeast of Oakland. No journey is complete without a visit to California State Railroad Museum, Old Sacramento State Historic Park and Crocker Art Museum.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.