$107 Find Cheap Flights from Oakland to Chicago - Compare and Save

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

• Earliest: departs at 5:10 am and lands at 9:12 am
• Latest: departs at 11:55 pm and lands at 3:57 am.

The flight takes about 4h 02m.

Two cabin classes are available on flights from Oakland to Chicago:

• Economy Class
• First Class

A nonstop flight from Oakland to Chicago takes 4h 02m, 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 Oakland to Chicago range from $352 to $564, with an average of $444 over the past 12 months. Anything below $352 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 35% above the $444 route average. Book 11 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $360 round-trip via Los Angeles (LAX), compared to $475 for nonstop.

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 Oakland to Chicago 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 $205 to $1,619. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Oakland to Chicago are currently lower than usual. Average one-way flight prices are about $156, which is 40% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

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

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

• Las Vegas Harry Reid Intl (LAS) - 29% of one-stop connections
• San Diego (SAN) - 23% of one-stop connections
• Salt Lake City (SLC) - 21% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 11% of one-stop connections

Yes. Flexible dates can save you up to 16% on flights from Oakland to Chicago. Tuesday is the cheapest departure day at $410 round-trip on average, while Monday is the most expensive at $484, a difference of $74.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only Southwest operates flights between Oakland and Chicago.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 04m, compared with 6h 07m via Hollywood Burbank (BUR) and 6h 24m via Los Angeles (LAX).

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

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Oakland to Chicago 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.

MDW has a nursing room in Concourse C, next to the yoga room. This room, well-furnished with comfy seats, features a hand washing station and clean utensils. If you're a breastfeeding mother, you can use this nursing room to breastfeed and change your infant privately before continuing your journey.

While waiting for your flight to Chicago at OAK, you should check out the airport's public art displays in Terminal 2, near the baggage claim area, and in Terminal 1, on the Airside. Additionally, there are a variety of retail shops throughout both terminals you can check out.

If you'd like to land at a Chicago airport with an on-site hotel, you should book a flight that lands at ORD, as this public transit hub is home to two on-site hotels, Hilton Chicago O'Hare Airport Hotel and Aloft Chicago O'Hare. Hilton Chicago O'Hare Airport Hotel is located opposite Terminal 2. It is connected to all the airport terminals via an underground Walkway. Aloft Chicago O'Hare is located between Terminals 1, 2, and 3. Since both hotels feature great amenities, staying at either would be a move you'll not regret.

Oakland International Airport has a lounge in Terminal 1, on the Airside, near Gates 8 and 8A. This relaxing space, referred to as the Escape lounge, is open to all economy travelers at the airport. If you're one, you can access it if you're open to purchasing a day pass, annual membership, or pay at the door.