- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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Journey information
Overview: Oakland, CA to Chicago, IL flight
USAUSA
Flights from Oakland, CA to Chicago, IL depart on average 43 times per day, taking around 6h 51m. Cheap flight tickets for this journey start at $145 but you can travel from only $144 by bus.
The earliest flight runs at 05:15, the last at 23:33. The fastest flight covers the 1845 miles (2970 km) distance in 5h 38m. September is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $144
Distance 1845 miles (2970 km) |
Average flight duration 6h 51m |
Cheapest ticket price $145 |
Flights per day 43 |
Fastest flight 5h 38m |
First flight 5:15 AM |
Last flight 11:33 PM |
Cheapest Month Sep |
Cheapest Day Thu |
High Season Jan - Mar |
Low Season Oct - Dec |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $144
Frequently asked questions about your Oakland, CA to Chicago, IL trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Oakland, CA to Chicago, IL.
Cheap plane tickets from Oakland, CA to Chicago, IL can start from as little as $145 when you book in advance. The average flight ticket price for Oakland, CA to Chicago, IL is $465 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The earliest flight from Oakland, CA to Chicago, IL leaves at 5:15 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Oakland, CA to Chicago, IL leaves at 11:33 PM.
There are {frequency} flights a day from Oakland, CA to Chicago, IL which require at least one change with {providers}. Schedules can vary on holidays or weekends with fewer flights.
Why should you book Oakland, CA to Chicago, IL flights with Omio?
Alaska Airlines operates all flights services from Oakland, CA to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Oakland, CA to Chicago, IL.
Why book with Omio vs Alaska Airlines?
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Alaska Airlines with all available travel options, which are train and bus to ensure you get the best deal for traveling from Oakland, CA to Chicago, IL.
Why book with Omio over Skyscanner, Trip or Edreams?
- Multiple modes of transport: Omio allows you to compare travel options including train and bus to find the ideal travel option from Oakland, CA to Chicago, IL.
Airlines: Alaska Airlines from Oakland, CA to Chicago, ILFind the best flights between Oakland, CA to Chicago, IL with Omio's travel partners Alaska Airlines from $144. We can find you the best deals, schedules and tickets when comparing and booking the best trip.
Alaska Airlines
About
Alaska Airlines, headquartered in SeaTac, Washington, is a major U.S. airline and the fifth-largest in North America by scheduled passengers carried as of 2024. Along with its regional partners, Horizon Air and SkyWest Airlines, Alaska Airlines operates a route network primarily connecting cities along the West Coast of the United States, including Alaska and Hawaii, to over 100 destinations in the contiguous U.S., the Bahamas, Belize, Canada, Costa Rica, Guatemala, and Mexico. The airline is a member of the Oneworld alliance, offering passengers access to a broad global network. Alaska Airlines is known for its customer service and loyalty program, Mileage Plan, and offers First Class, Premium Class, and Main Cabin seating options. The airline's primary hub is Seattle-Tacoma International Airport. In 2024, its parent company, Alaska Air Group, acquired Hawaiian Airlines.
Luggage & cancellation policy
Average Alaska Airlines Duration
5h 38m
Cheapest Alaska Airlines Price
$145
Alaska Airlines frequency
43 a day
Luggage included
1 carry-on bag (22 x 14 x 9) and 1 personal item included
Additional luggage
Checked bags fees start at $30 for first bag, $40 for second bag
Cancellation Policy
Saver fares are non-refundable. Main and First Class fares are refundable with fee, depending on fare type and elite status
Pregnant on board
Passengers can fly up to 36 weeks pregnant. After 28 weeks, medical certificate required
Unaccompagned minor
Unaccompanied minor service available for children ages 5-17. Service fee is $50 per direction on nonstop flights
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Alaska Airlines provides wheelchair assistance and special services for passengers with disabilities, including meet-and-assist services and accessible seating
Pets
Pets allowed in cabin and cargo hold. Service animals welcome. Fees apply for pets in cabin ($100)
Entertaiment on board
Companies, tickets, and onboard amenities between Oakland, CA and Chicago, IL
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
When taking a flight from Oakland, CA to Chicago, IL, you can count on Alaska Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Oakland, CA and Chicago, IL and compare the amenities they offer before buying a plane ticket.
For international flights we recommend to arrive 2.5 to 3 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Plan your visit to Chicago, IL
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Chicago, IL.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
FAQs: Oakland, CA to Chicago, IL Flight
Find answers to the most common questions about traveling from Oakland, CA to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.
It's helpful to compare your options as there are 2 ways to travel between Oakland, CA and Chicago, IL including taking a train and bus.
popular airports
Popular airports from Oakland, CA to Chicago, IL
Most Oakland, CA to Chicago, IL flights use the Oakland International Airport to O'Hare International Airport airport pair. Use this guide to compare Oakland, CA and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Oakland
Arrival airports in Chicago
Which Oakland, CA airport do flights to Chicago, IL leave from?
Flights from Oakland, CA to Chicago, IL depart from Oakland International Airport. The airport is 3 miles (5 km) from Oakland, CA city centre at 1 Airport Dr, Oakland, CA 94621, USA.
Oakland International Airport (OAK)1 Airport Dr, Oakland, CA 94621, USA
City-centre transport
Getting to Oakland International Airport from Oakland city centre
Oakland International Airport is 5 km from Oakland city centre. Public transport options include:
SubwayGrey-S · 20m · $5 · every ~21 min
Oakland International Airport airport facilities and services
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 and drink
Food options include: Restaurants are located in both terminals; options include fast food and sit-down dining, such as Peet's Coffee and Subway.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located in both terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at Oakland International Airport: Parking, Taxis, WC.
Bike and car services
Available at Oakland International Airport: Car Rental.
Accessibility
Accessibility facilities are available at Oakland International Airport: Ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels within walking distance, Hilton Oakland Airport is nearby..
Which Chicago, IL airport do flights from Oakland, CA arrive at?
Flights from Oakland, CA to Chicago, IL arrive at O'Hare International Airport. O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · $6 · every ~23 min
O'Hare International Airport airport facilities and services
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 and drink
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.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Airports for flights from Oakland, CA to Chicago, IL
See which airports are used for flights between Oakland, CA and Chicago, IL, including airport details.
Flights from Oakland, CA to Chicago, IL generally leave from Oakland International Airport and arrive in O'Hare International Airport.Oakland International Airport is 3 miles (5 km) away from Oakland, CA city centre and O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.
More options for your journey from Oakland, CA to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Oakland, CA
Most popular flights to Chicago, IL
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