- Must visit
Oakland Museum of California
Major art museum focused on California history, art, and social impact, with strong collections and a lively modern campus.
Flights from Chicago, IL to Oakland, CA depart on average 34 times per day, taking around 12h 54m. Cheap flight tickets for this journey start at $326 (€266) but you can travel from only $185 (€150) by bus.
The earliest flight runs at 00:43, the last at 23:33. The fastest flight covers the 1845 miles (2970 km) distance in 7h 16m. May is the cheapest month to fly.
Distance 1845 miles (2970 km) |
Average flight duration 12h 54m |
Cheapest ticket price $326 (€266) |
Flights per day 34 |
Fastest flight 7h 16m |
First flight 12:43 AM |
Last flight 11:33 PM |
Cheapest Month May |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 56 days |
Omio recommends booking the train as it is the most popular option from Chicago, IL to Oakland, CA among Omio's users. If you are prioritising price take the bus with prices starting from $185. For those with little time consider booking a flight which can get you there in 12h 54m. The ticket price range depends on the travel mode: a bus costs an average of $185, and a train costs an average of $237.
Distance: 1845 miles (2970 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$428 Average price | $485 Average price | $375 Average price Cheapest | $430 Average price (fuel + tolls) |
15h 54m Average total duration Fastest 12h 54m Onboard + 3h 0m Additional time* | 57h 33m Average total duration 57h 3m Onboard + 30m Additional time* | 51h 26m Average total duration 50h 56m Onboard + 30m Additional time* | 31h 5m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Oakland, CA:
A bus is $53 (€43) less than a flight for this route with tickets for a flight from Chicago, IL to Oakland, CA costing on average $428 (€348).
A bus is $109 (€89) less than a train for this route with tickets for a train from Chicago, IL to Oakland, CA costing on average $485 (€394).
Other travel options to Oakland, CA take longer:
Bus takes on average 50h 56m.
Train takes on average 57h 3m.
The table below shows live departures for Chicago, IL to Oakland, CA flights for today, Wednesday, August 5. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 1:00 PM Chicago, IL | 11h46 | 12:46 AM Oakland, CA | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Oakland, CA — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Oakland, CA trip today.
Major art museum focused on California history, art, and social impact, with strong collections and a lively modern campus.
Independent museum preserving Black Panther Party history through photographs, artifacts, and community-centered interpretation in West Oakland.
Children's museum and cultural center with hands-on exhibits celebrating Black creativity, history, and family learning experiences.
Beloved urban lake ringed by paths, gardens, and skyline views, ideal for walking, birdwatching, and experiencing everyday Oakland life.
Waterfront promenade and marina district with bay views, sailing activity, and sunset walks near Oakland's western edge.
Large hillside park with redwoods, trails, and picnic areas, offering a peaceful escape and classic East Bay outdoor scenery.
Smoked beef brisket with a peppery bark, reflecting Oakland’s strong barbecue culture shaped by Southern Black migration and longtime neighborhood smokehouses.
A tangy, mayo-based cabbage side commonly served with Oakland barbecue. It is a staple pairing at local smokehouses and cookouts.
Crisp fried chicken often served with waffles or sides, tied to Oakland’s soul food tradition and beloved at classic neighborhood restaurants.
Refined tasting-menu restaurant highlighting seasonal California ingredients with polished service and an elegant, modern dining room.
Longtime Ethiopian restaurant praised for injera platters, stews, and traditional coffee in a welcoming, community-focused space.
Celebrated Oakland Chinatown destination for handmade noodles and dumplings in a busy, casual setting with strong local following.
Oakland is moderate for US cities: lodging is often high, but dining and BART or buses are usually cheaper than in San Francisco.
Tip 18-20% at restaurants, 15-20% for taxis or rideshares, and $1-2 per drink or coffee is appreciated.
Find answers to the most common questions about traveling from Chicago, IL to Oakland, CA by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Oakland, CA, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Oakland, CA flights use the O'Hare International Airport to Oakland International Airport airport pair. Use this guide to compare Chicago, IL and Oakland, CA airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Oakland International Airport is 5 km from Oakland city centre. Public transport options include:
Oakland International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in both terminals; options include fast food and sit-down dining, such as Peet's Coffee and Subway.
Free Wi-Fi available throughout the airport. ATMs are located in both terminals.
Lost and found is available at the station.
Available at Oakland International Airport: Parking, Taxis, WC.
Available at Oakland International Airport: Car Rental.
Accessibility facilities are available at Oakland International Airport: Ramps, toilets.
Nearby hotels include Hotels within walking distance, Hilton Oakland Airport is nearby..
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