Cheap Flights from Chicago (CHIA) to Oakland Metropolitan Oak (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 Airport

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 £188. Find the lowest prices on one-way and return tickets right here.

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 April.

Direct flights from Chicago to Oakland Metropolitan Oak

Chicago to Oakland: Flight information

The things to know before you go.
Cheapest flight found£89
Cheapest month to flyApril
Average flight time4 hrs, 34 mins
Most popular airlineSouthwest Airlines
Average flights per week10

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 £188. 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 34 minutes is the average flight time from Chicago to Oakland Metropolitan Oak.
Southwest Airlines flies direct from Chicago to Oakland Metropolitan Oak.
As of April 2026, there are 10 flights per week flying from Chicago to Oakland Metropolitan Oak.
The cheapest month to fly from Chicago to Oakland Metropolitan Oak is usually May.
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 Monday, 11 May 2026.
Yes – the average flight time is 4 hours and 34 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 Metropolitan Oakland International Airport (OAK): What you need to know

  • Begin your trip planning by looking up the ideal departure point for your flight from Chicago to Metropolitan Oakland International Airport (OAK). Explore your options for setting off from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), the city's main airports.

  • Metropolitan Oakland International Airport is located in Oakland. The city operates on the UTC-7 timezone and is two hours behind Chicago.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to catch your flight from Chicago to OAK.

  • In peak travel periods, allow for longer wait times and show up earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international trips.

Airports in Chicago

O'Hare International Airport (ORD)

  • Travelling from central Chicago to ORD takes about 55 minutes on public transport. If you ride-share, drive or grab a cab, you'll cover the 40 kms (25 miles) in 35 minutes or so, depending on traffic.

  • Want an easy start to your holiday? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Metropolitan Oakland International Airport or prefer not to rush, these hotels are just the thing:

  • Of all flights departing from O'Hare International Airport, 74.85% touch down on time at their destination.

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

Chicago Midway International Airport (MDW)

  • You can book a direct Chicago to Metropolitan Oakland International Airport (OAK) plane ticket out of Chicago Midway International Airport (MDW). Figure out if flying from MDW works better for your plans.

  • Catch your direct flight from Chicago to OAK with Southwest Airlines. This is one of the leading airlines operating this route out of MDW.

  • Southwest Airlines is the go-to airline for bookings on the MDW to OAK route.

  • Southwest Airlines is the most punctual carrier flying from Chicago Midway International Airport to Metropolitan Oakland International Airport, with 65.67% of its services arriving as planned.

  • You can arrive at MDW from the centre of Chicago in approximately 20 minutes by car, depending on traffic conditions. The journey by public transport takes roughly 45 minutes to travel the 19 kms (12 miles) or so.

  • Kick off your holiday early with an additional night away from home. Before your Chicago to OAK flight, unwind in one of these hotels close to Chicago Midway International Airport:

  • When it comes to flight punctuality, Chicago Midway International Airport has an on-time arrival performance of 77.88%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The trip to RFD from the centre of Chicago is around 4 hours 15 minutes by public transport. If you prefer to travel by car, it'll take you about 1 hour 25 minutes to cover the 137 kms (85 miles) or so.

  • Skip the morning rush on departure day — stay near Chicago Rockford International Airport and know you'll reach your gate with time to spare. Settle in at one of these hotels the day before if you have an early Chicago to Metropolitan Oakland International Airport flight:

  • The on-time performance rate of RFD is 76.19%. In other words, that's how often flights that depart this airport reach their final stop as planned.

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

About Metropolitan Oakland International Airport (OAK)

Getting from Metropolitan Oakland International Airport (OAK) to central Oakland

  • Metropolitan Oakland International Airport to the centre of Oakland is around 7 miles. If you're getting a cab or renting a car, do some research to make your trip as easy as possible. Journey times will vary depending on the time of day and traffic conditions.

  • It'll take around 40 minutes if you're travelling by public transport.

How to find the cheapest flights from Chicago to Metropolitan Oakland International Airport (OAK)

  • The cheapest price we've found for a one-way ticket from Chicago to Metropolitan Oakland International Airport is £89. For a return flight on this route, the best price is £188. Depending on when and how early you book, these fares can change.

  • Don't wait until the last moment. You're more likely to find cheap flights from Chicago to OAK if you book early. Airlines often offer some fantastic early bird rates.

  • Affordable Chicago to Metropolitan Oakland International Airport tickets are easier to find if your travel dates are flexible. Try using the 'Whole month' search function to compare fares across each month and then choose the cheapest day.

  • Snapping up a cheap plane ticket from Chicago to OAK is a piece of cake with Price Alerts. Simply create one of these automatic alerts and we'll notify you as soon as the price has dropped.

  • Filters make it easier to snap up a deal on your flight from Chicago to Metropolitan Oakland International Airport. Choose the departure times, airlines and number of stops that make sense for you. Then sort the results by 'Cheapest' to bring up the lowest fares right away.

The best time to fly from Chicago to Metropolitan Oakland International Airport (OAK)

  • May is the quietest month for flights from Chicago to Metropolitan Oakland International Airport (OAK), while July is the most popular. Pick the best time to visit Oakland based on whether you like a bustling atmosphere or a more laid-back vibe.

  • Lock in a Chicago to OAK plane ticket departing in September if you want to explore the city during its warmest month. You can expect temperatures in Oakland to range from 12ºC (54ºF) to 26ºC (79ºF).

  • January sees temperatures of between 4ºC (39ºF) and 17ºC (63ºF). Look for cheap tickets from Chicago to Metropolitan Oakland International Airport around that time if you like travelling in cooler conditions.

More about Oakland

  • When it comes to looking for somewhere to lay your head, you'll find the most popular stays in Oakland right here. Browse these options after locking in your flight from Chicago to Metropolitan Oakland International Airport:

  • Your trip to Oakland isn't complete without checking out the sights. Attractions worth exploring include Bay Area, Fox Theatre and African American Museum and Library.

Explore more of the United States

  • Fresno is just one of the many places in the United States waiting to be explored once you've seen Oakland. Around 241 kms (150 miles) away to the south-east, top sights here include Forestiere Underground Gardens, Shinzen Japanese Garden and Fresno Chaffee Zoo.

  • Sacramento is another favourite destination in the United States and is around 113 kms (70 miles) north-east of Oakland. No journey is complete without visiting Old Sacramento Waterfront, Fright Planet - America's Haunted Theme Park and California State Railroad Museum.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.