$127 Find Cheap Flights from Chicago to Oakland - Compare and Save

These are the earliest and latest flight times available from Chicago to Oakland:

• Earliest: departs at 9:35 am and lands at 2:18 pm
• Latest: departs at 11:05 pm and lands at 3:48 am.

The flight takes about 4h 43m.

Only Economy Class is available on flights from Chicago to Oakland.

A nonstop flight from Chicago to Oakland takes 4h 43m, covering 1,845 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Chicago to Oakland range from $303 to $530, with an average of $400 over the past 12 months. Anything below $303 counts as a good deal.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $354 round-trip via San Diego (SAN), compared to $393 for nonstop.

Southwest is the only airline operating Chicago to Oakland flights. 67% of its flights are on time.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Chicago to Oakland flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $233 to $1,499. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago to Oakland are currently lower than usual. Average one-way flight prices are about $162, which is 44% below the typical average for this route.

Oakland Airport (OAK) hosts 5 major car rental companies, with daily rates starting from around $21 for economy cars. Top options include:

• Dollar
• Thrifty
• Budget
• Hertz
• Alamo

Flights from Chicago to Oakland may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Oakland (OAK).

Morning flights have the fewest delays on this route, while night departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Oakland route, 33% of flights were delayed in the past 3 months, with delays averaging 2h 13m.

One-stop flights from Chicago to Oakland most commonly connect through:

• Salt Lake City (SLC) - 30% of one-stop connections
• Seattle/Tacoma Intl (SEA) - 19% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 18% of one-stop connections
• San Diego (SAN) - 16% of one-stop connections

Yes. Flexible dates can save you up to 32% on flights from Chicago to Oakland. Saturday is the cheapest departure day at $349 round-trip on average, while Sunday is the most expensive at $507, a difference of $158.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Only Southwest operates flights between Chicago and Oakland.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 17m, compared with 6h 26m via Phoenix Sky Harbor Intl (PHX) and 6h 26m via Kansas City (MCI).

Oakland is 2 hours behind Chicago (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Oakland are Oakland Arena, Fox Theater and Jack London Square. These are among the most viewed places in Oakland on KAYAK.

Among airlines operating Chicago to Oakland flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

There are various lounge facilities within the different terminals at the airport. The main lounge in Terminal 1 is the United Club by United airlines which has four lounges: near Gates C16, C18, B18, and B6. The other is the Delta Sky Club in Terminal 2, where United Club also has a place on the grid. There are also multiple other lounge facilities in Terminal 3, mainly occupied by American Airlines. Additionally, the Admiral Club lounges are located between Gates H6 and K6, Gate L1, and near Gate G8. Terminal 5 has some lounges in it.

The SpringHill Suites by Marriott Oakland Airport is among the most convenient hotels where you can book a room in the case of late arrival at the airport. It is located 1.7 miles away and has facilities such as an indoor spa.

There are several Pet Relief Areas in O'Hare International Airport (ORD). An area inside Terminal 1's lower level is accessible by taking the elevator to the lower level and proceeding to the Baggage Claim, exit through Door 1A, and you will have the area on your left. Terminal 2's location is accessible by taking the elevator to the lower level, exiting through Door 2E, and the site will also be on your left. Terminal 3 is located inside the Main Hall of the airport next to the Lotto booth found near Gate K1.

There are both direct and connecting flights between the destinations. Spirit Airlines is the only airline that offers direct flights between the destinations. However, they also have flights with a layover at Harry Reid International Airport (LAS). Delta Airlines also makes flights with a layover at Salt Lake City International Airport (SLC).