Oakland, CA OAK to Chicago, IL CHI flight with Alaska Airlines

Sun, Sep 20
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Journey information

Overview: Oakland, CA to Chicago, IL flight

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Flights from Oakland, CA to Chicago, IL depart on average 31 times per day, taking around 6h 50m. Cheap flight tickets for this journey start at €158 if you book in advance.

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. March 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
Distance
1845 miles (2970 km)
Average flight duration
6h 50m
Cheapest ticket price
€158
Flights per day
31
Fastest flight
5h 38m
First flight
5:15 AM
Last flight
11:33 PM
Cheapest Month
Mar
Cheapest Day
Mon
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

The cheapest and fastest flights from Oakland, CA to Chicago, IL

Showing times, prices and bookable tickets for Sep 20

Cheapest price on Sep 20

€305

Average ticket price on Sep 20

€305

Fastest journey on Sep 20

1 d 1 h 30 m

Average journey duration on Sep 20

1 d 1 h 30 m

Flights on Sep 20

1

Distance

2970 km

Cheap tickets

The best way to find a cheap flight ticket from Oakland, CA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Oakland, CA to Chicago, IL will cost around €305 if you buy it on the day, but the cheapest tickets can be found for only €305.

Fast flights

On Sun, Sep 20, we found 1 flights from Oakland, CA to Chicago, IL, including 1 direct services.

On Sun, Sep 20 the direct flights cover the 2970 km distance in an average of 1 d 1 h 30 m but if you time it right, some flights will get you there in just 1 d 1 h 30 m .

On Sun, Sep 20 the longest flights will take 1 d 1 h 30 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

  • Alaska Airlines
    4:43 PM25h30
    Oakland, CA
    6:13 PMChicago, IL
    €3051One-way
    0 transfers

Travel Information

Compare train and bus for Oakland, CA to Chicago, IL

Omio recommends booking the train as it is the most popular option from Oakland, CA to Chicago, IL among Omio's users. If you are prioritising price, take the bus, with an average ticket price of €265 For those with little time, consider booking a bus, which has an average total journey time of 54h 24m. Average ticket prices depend on the travel mode: a bus costs an average of €265, while a train costs an average of €428.

Distance: 1845 miles (2970 km)

Compare train with

Most popular
Train
Bus

€428

Average price

€265

Average price

Cheapest

56h 51m

Average total duration

56h 21m

Onboard

+

30m

Additional time*

54h 24m

Average total duration

Fastest

53h 54m

Onboard

+

30m

Additional time*

Amtrak

Most popular train company

Greyhound

Most popular bus company

Direct Options

Direct Options

The cheapest way to travel from Oakland, CA to Chicago, IL is a bus with an average price of €265.

This is compared to other travel options from Oakland, CA to Chicago, IL:

A bus is €163 less than a train for this route with tickets for a train from Oakland, CA to Chicago, IL costing on average €428.

A bus is €292 less than a flight for this route with tickets for a flight from Oakland, CA to Chicago, IL costing on average €557.

The fastest way to travel from Oakland, CA to Chicago, IL is by flight with an average journey time of 6h 50m.

Other travel options to Chicago, IL take longer:

Bus takes on average 53h 54m.

Train takes on average 56h 21m.

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.
We recommend using the train as it is the most popular way to get from Oakland, CA to Chicago, IL among Omio's users.

Live departures

Oakland, CA to Chicago, IL flight times

The table below shows live departures for Oakland, CA to Chicago, IL flights for today, Saturday, September 19. You can also manually refresh the results below to see updated flight journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
Alaska AirlinesAS3111 · AS1368 · AS5386:48 AM Oakland International Airport
15h11
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3111 · AS609 · AS5386:48 AM Oakland International Airport
15h11
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3111 · AS14466:48 AM Oakland International Airport
28h34
1:22 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3111 · AS14786:48 AM Oakland International Airport
10h33
7:21 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3266 · AS452 · AS3288:04 AM Oakland International Airport
20h16
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS1701 · AS5388:04 AM Oakland International Airport
13h55
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS790 · AS5388:04 AM Oakland International Airport
13h55
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS743 · AS3288:04 AM Oakland International Airport
20h16
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS790 · AS3288:04 AM Oakland International Airport
20h16
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS1536 · AS3288:04 AM Oakland International Airport
20h16
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS1536 · AS5388:04 AM Oakland International Airport
13h55
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3266 · AS3248:04 AM Oakland International Airport
27h22
1:26 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3266 · AS2243 · AS5388:04 AM Oakland International Airport
13h55
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS735 · AS26510:11 AM Oakland International Airport
26h43
2:54 PM O'Hare International Airport1 transfer
Alaska AirlinesAS735 · AS32810:11 AM Oakland International Airport
18h09
6:20 AM O'Hare International Airport1 transfer
Alaska AirlinesAS735 · AS41010:11 AM Oakland International Airport
23h56
12:07 PM O'Hare International Airport1 transfer
Alaska AirlinesAS735 · AS53810:11 AM Oakland International Airport
11h48
11:59 PM O'Hare International Airport1 transfer
Alaska AirlinesAS2375 · AS32411:55 AM Oakland International Airport
23h31
1:26 PM O'Hare International Airport1 transfer
Alaska AirlinesAS2375 · AS743 · AS32811:55 AM Oakland International Airport
16h25
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS2375 · AS1701 · AS32811:55 AM Oakland International Airport
16h25
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS2375 · AS1701 · AS53811:55 AM Oakland International Airport
10h04
11:59 PM O'Hare International Airport2 transfers
Alaska AirlinesAS2375 · AS452 · AS32811:55 AM Oakland International Airport
16h25
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3107 · AS14781:29 PM Oakland International Airport
27h52
7:21 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3107 · AS574 · AS3281:29 PM Oakland International Airport
14h51
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3107 · AS683 · AS3281:29 PM Oakland International Airport
14h51
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3107 · AS1373 · AS3281:29 PM Oakland International Airport
14h51
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS3107 · AS14461:29 PM Oakland International Airport
21h53
1:22 PM O'Hare International Airport1 transfer
Alaska AirlinesAS536 · AS434 · AS3242:15 PM Oakland International Airport
21h11
1:26 PM O'Hare International Airport2 transfers
Alaska AirlinesAS536 · AS2325 · AS3242:15 PM Oakland International Airport
21h11
1:26 PM O'Hare International Airport2 transfers
Alaska AirlinesAS536 · AS2652:15 PM Oakland International Airport
22h39
2:54 PM O'Hare International Airport1 transfer
Alaska AirlinesAS536 · AS2125 · AS3242:15 PM Oakland International Airport
21h11
1:26 PM O'Hare International Airport2 transfers
Alaska AirlinesAS536 · AS5382:15 PM Oakland International Airport
7h44
11:59 PM O'Hare International Airport1 transfer
Alaska AirlinesAS536 · AS4102:15 PM Oakland International Airport
19h52
12:07 PM O'Hare International Airport1 transfer
Alaska AirlinesAS536 · AS3282:15 PM Oakland International Airport
14h05
6:20 AM O'Hare International Airport1 transfer
Alaska AirlinesAS3103 · AS683 · AS4103:13 PM Oakland International Airport
18h54
12:07 PM O'Hare International Airport2 transfers
Alaska AirlinesAS3103 · AS14783:13 PM Oakland International Airport
26h08
7:21 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3103 · AS14463:13 PM Oakland International Airport
20h09
1:22 PM O'Hare International Airport1 transfer
Alaska AirlinesAS3103 · AS683 · AS3283:13 PM Oakland International Airport
13h07
6:20 AM O'Hare International Airport2 transfers
Alaska AirlinesAS2103 · AS14785:10 PM Oakland International Airport
24h11
7:21 PM O'Hare International Airport1 transfer
Alaska AirlinesAS2103 · AS14935:10 PM Oakland International Airport
28h49
11:59 PM O'Hare International Airport1 transfer
Alaska AirlinesAS2103 · AS14465:10 PM Oakland International Airport
18h12
1:22 PM O'Hare International Airport1 transfer
Alaska AirlinesAS1359 · AS4107:51 PM Oakland International Airport
14h16
12:07 PM O'Hare International Airport1 transfer
Alaska AirlinesAS1359 · AS2657:51 PM Oakland International Airport
17h03
2:54 PM O'Hare International Airport1 transfer
Alaska AirlinesAS1359 · AS3287:51 PM Oakland International Airport
8h29
6:20 AM O'Hare International Airport1 transfer
Alaska AirlinesAS1359 · AS5387:51 PM Oakland International Airport
26h08
11:59 PM O'Hare International Airport1 transfer

Find all the dates and times for this journey

Compare prices and tickets Oakland, CA to Chicago, IL by train or bus

Compare train and bus 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.

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Oct 09

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

Art Institute of Chicago

World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.

View on mapVisit website
  • Must visit

Field Museum

Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.

View on mapVisit website
  • 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.

View on mapVisit website

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.

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.

FAQs
Cheap plane tickets from Oakland, CA to Chicago, IL can start from as little as €158 when you book in advance. The average flight ticket price for Oakland, CA to Chicago, IL is €557 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Oakland, CA to Chicago, IL is 5h 38m to travel the 1845 miles (2970 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
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.
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 1 miles (3 km) from Chicago, IL city centre.
The cheapest month for a flight from Oakland, CA to Chicago, IL is March.
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.
Since neither Oakland, CA nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 2 h between Oakland, CA and Chicago, IL all year round.
The best events to attend in Chicago, IL include:
  • Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
  • Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
  • Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
Some of the most interesting sights to explore in Chicago, IL are:
  • Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
  • Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
  • Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
  • Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
  • Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best holidays to experience in Chicago, IL include:
  • Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
  • Independence Day, spectacular fireworks and festive celebrations throughout the city
  • Labor Day, a lively atmosphere with various festivals and pleasant weather.
The best things to do in Chicago, IL include:
  • Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
  • Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
  • Take a river cruise to see the city's iconic architecture from a different perspective
  • Attend a live performance at the historic Chicago Theatre
  • Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
We recommend using the train as it is the most popular way to get from Oakland, CA to Chicago, IL among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 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.
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.

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, USAWifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rental
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 · €4 · 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..

More about Oakland International Airport

More options for your journey from Oakland, CA to Chicago, IL

Here are some other resources that might have the information you need

Return journeys for flights from Chicago, IL to Oakland, CA
Buses from Oakland, CA to Chicago, IL
More information on flights to Oakland, CA
More information on flights to Chicago, IL

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