- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
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Journey information
Overview: Oakland, CA to Chicago, IL flight
USAUSA
Flights from Oakland, CA to Chicago, IL depart on average 29 times per day, taking around 21h 49m. Cheap flight tickets for this journey start at $337 (€276) but you can travel from only $248 (€203) by bus.
There are 1 flights per day. The earliest flight runs at 05:15, the last at 23:33. The fastest flight covers the 1845 miles (2970 km) distance in 18h 8m. July 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 $248 (€203)
Distance 1845 miles (2970 km) |
Average flight duration 21h 49m |
Cheapest ticket price $337 (€276) |
Flights per day 29 |
Direct flights 1 |
Fastest flight 18h 8m |
First flight 5:15 AM |
Last flight 11:33 PM |
Cheapest Month Jul |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Jul - Sep |
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 $248 (€203)
The cheapest and fastest flights from Oakland, CA to Chicago, IL
Showing times and prices for Jun 23
Cheapest price
$337
Average price
$337
Fastest journey
18 h 8 m
Average duration
18 h 8 m
Flights per day
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 $337 if you buy it on the day, but the cheapest tickets can be found for only $337.
Fast flights
Of the 1 flights that leave Oakland, CA for Chicago, IL onTue, Jun 23, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Jun 23 the direct flights cover the 2970 km distance in an average of 18 h 8 m but if you time it right, some flights will get you there in just 18 h 8 m .
On Tue, Jun 23 the longest flights will take 18 h 8 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.
12:03 AM18h08Oakland, CA6:11 PMChicago, IL$3371One-way0 transfers
- 12:03 AM18h08Oakland, CA6:11 PMChicago, IL$3371One-way0 transfers
Travel Information
Compare train, bus, and flight 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 prices starting from $248. For those with little time consider booking a flight which can get you there in 21h 49m. The ticket price range depends on the travel mode: a bus costs an average of $248, and a train costs an average of $288.
Distance: 1845 miles (2970 km)
Compare flight with
| Flight | Most popular Train | Bus |
|---|---|---|
$355 Average price | $501 Average price | $331 Average price Cheapest |
24h 49m Average total duration Fastest 21h 49m Onboard + 3h 0m Additional time* | 52h 53m Average total duration 52h 23m Onboard + 30m Additional time* | 57h 29m Average total duration 56h 59m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Oakland, CA to Chicago, IL is a bus with an average price of $331 (€271).
This is compared to other travel options from Oakland, CA to Chicago, IL:
A bus is $24 (€20) less than a flight for this route with tickets for a flight from Oakland, CA to Chicago, IL costing on average $355 (€291).
A bus is $170 (€139) less than a train for this route with tickets for a train from Oakland, CA to Chicago, IL costing on average $501 (€410).
The fastest way to travel from Oakland, CA to Chicago, IL is by flight with an average journey time of 21h 49m.
Other travel options to Chicago, IL take longer:
Train takes on average 52h 23m.
Bus takes on average 56h 59m.
It's helpful to compare your options as there are 3 ways to travel between Oakland, CA and Chicago, IL including taking a train, bus, and flight.
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, Sunday, June 21. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 4:43 PM Oakland, CA | 25h30 | 6:13 PM Chicago, IL | 0 transfersDirect | |
| Monday, June 22 | |||||
| 12:03 AM Oakland, CA | 18h08 | 6:11 PM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Oakland, CA to Chicago, IL by train, bus, or flight
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.
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Complete guide to Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
- Must visit
Millennium Park
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
- Must visit
The Magnificent Mile
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
- Must visit
Chicago Riverwalk
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 20-40 per person at a mid-range restaurant.
- Fine dining
- USD 75+ per person before drinks and tax.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
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.
Cheap plane tickets from Oakland, CA to Chicago, IL can start from as little as $337 (€276) when you book in advance. The average flight ticket price for Oakland, CA to Chicago, IL is $355 (€291) ; 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 18h 8m 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 July.
It's helpful to compare your options as there are 3 ways to travel between Oakland, CA and Chicago, IL including taking a train, bus, and flight.
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
Oakland
Chicago
The major airport for departures in Oakland is Oakland International Airport. Find all the information you need to know about services, amenities and connections at Oakland International Airport for your trip from Oakland to Chicago.
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Shower
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
5 km
Car connection
I-880, exit 98Wifi
- Free Wi-Fi available throughout the airport
Shopping
- Shops are available in both terminals, main shops include Hudson News and Duty-Free
Parking
- Parking available near the terminal, approximately 0.52€ (20 THB) per hour
Dining
- Restaurants are located in both terminals; options include fast food and sit-down dining, such as Peet's Coffee and Subway.
Taxis
- Available outside the terminal
Accessibility
- Ramps, toilets
WC
- Available throughout the airport
Hotel
- Hotels within walking distance, Hilton Oakland Airport is nearby.
Shower
- Showers are available in some lounges; access may require a lounge pass
Lounge
- Lounges available, including Escape Lounge in terminal 1
Lost and Found Office
- Lost and Found located in terminal 1
Car Rental
- Car rental services are available on-site from companies like Hertz and Avis
Public transit options for Oakland International Airport
- BART, Coliseum Station, 8 miles
The major airport for arrivals in Chicago is O'Hare International Airport. Find all the information you need to know about services, amenities and connections at O'Hare International Airport for your journey to Chicago from Oakland.
Amenities at airport
WifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rentalinformation
Distance to city center
3 kmCar connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership
Lounge
- Lounges available, including United Club and American Airlines Admirals Club
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
Most popular flights from Oakland, CA
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
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