Cheap Flight Tickets from Chicago (MDW) to Oakland (OAK), Starting at $591

Good to Know: Cheapest and Fastest MDW - OAK Flights

Useful information for finding best airline tickets from Chicago Midway International to Metropolitan Oakland International on your next trip.

Cheapest Round Trip Flight

$596

WN Southwest Airlines • 1 stop • 11h 55m

Aug 13 – Aug 17

The cheapest round trip flight from Chicago to Oakland (MDW-OAK-MDW) is currently $596

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Cheapest Direct Flight

$591

WN Southwest Airlines • nonstop • 7h 10m

Aug 13

The cheapest nonstop flight from Chicago to Oakland (MDW-OAK) is currently $591

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Fastest Flight

7h 5m

The fastest nonstop flight from Chicago to Oakland (MDW-OAK) takes 7h 5m

Top Airlines Flying from Chicago to Oakland

Southwest Airlines-WN

Southwest Airlines

Latest Flight Deals from Chicago (MDW) to Oakland (OAK)

Compare and book low fare round-trip air tickets from Chicago to Oakland. Ideal for travelers with confirmed return itineraries.

Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
11h 55m
3:55 PM - 9:10 PM • 1 stop
WN
Chicago → Oakland
6h 40m
11:55 PM - 5:55 AM • nonstop
$596
Southwest Airlines
Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
11h 50m
4:00 PM - 9:10 PM • 1 stop
WN
Chicago → Oakland
6h 45m
5:20 AM - 11:25 AM • nonstop
$601
Southwest Airlines
Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
7h 10m
8:35 PM - 11:05 PM • nonstop
WN
Chicago → Oakland
11h 50m
7:50 AM - 5:00 PM • 2 stops
$601
Southwest Airlines
Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
10h 35m
10:15 AM - 2:50 PM • 1 stop
WN
Chicago → Oakland
6h 40m
11:55 PM - 5:55 AM • nonstop
$601
Southwest Airlines
Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
12h 5m
10:15 AM - 3:40 PM • 1 stop
WN
Chicago → Oakland
6h 45m
5:20 AM - 11:25 AM • nonstop
$601
Southwest Airlines
Aug 13 - Aug 17, Economy
WN
Chicago → Oakland
12h 20m
1:50 PM - 7:30 PM • 2 stops
WN
Chicago → Oakland
11h 50m
7:50 AM - 5:00 PM • 2 stops
$612
Southwest Airlines

Fly from Chicago to Oakland with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Oakland? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Oakland Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to OAK?
The most popular airline flying from Chicago to Oakland are
Can I fly from MDW to OAK non-stop?
Yes, you can fly MDW to OAK non-stop on
Which airlines fly nonstop between Chicago and Oakland?
The non-stop flights between Chicago and Oakland are .
What’s the earliest departure time from MDW to OAK Airport?
The earliest flight leaves MDW at 10:15 am and lands in OAK - Metropolitan Oakland International
What are the airports in Oakland?
OAK
Can I make changes to my Chicago to Oakland flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to OAK?
Read the fare rules of the Chicago to Oakland air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Oakland?
operate flights between Chicago and Oakland
How long does a flight from Chicago to Oakland take?
It takes approximately 4 hour to fly non-stop from MDW to OAK, which is 1844.21 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Oakland (OAK) ?
In the past couple of days, the cheapest tickets to OAK from MDW were found on WN : USD 601
Do I need a passport to fly between MDW and OAK?
No
What’s the latest departure time from MDW to OAK ?
The last flight leaves MDW at 8:35 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to oak?
You can find affordable flights from Chicago Midway International Airport (mdw) to Metropolitan Oakland International Airport (oak) on Southwest Airlines. For a luxury experience, consider booking a First cabin suite. It's recommended to book at least 25 days in advance for the best Low Fares. You can also explore other airlines and airfare options through fareleaders.com for budget-friendly flights.
What's the popular airline to fly from mdw to oak?
You can fly from Chicago Midway International Airport (mdw) to Metropolitan Oakland International Airport (oak) on Southwest Airlines. This is a popular airline option, known for its budget-friendly flights. Booking in advance will ensure the best rates. For your one-way trip, consider making your reservation at least 25 days prior to your desired travel date.
What's the cheapest day of the week to fly from mdw to oak?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Metropolitan Oakland International Airport (oak) is typically on Fridays. This is based on historical data and flight schedules, which often show lower airfare prices for this route on Fridays.
What's the cheapest month to fly from mdw to oak?
The cheapest month to fly from Chicago Midway International (mdw) to Metropolitan Oakland International (oak) is November. Flying during this time can result in budget-friendly flights, making it an excellent choice for travelers looking for affordable airfare options.
Which airline/airlines fly from mdw to oak?
The airlines that fly from Chicago Midway International Airport (mdw) to Metropolitan Oakland International Airport (oak) include Aer Lingus, WestJet Airlines, Brussels Airlines, British Airways, American Airlines, Volaris Airline, Southwest Airlines, Air Tahiti Nui, Delta Airlines, and Porter Airline. You can find the best airfare deals on these airlines' websites or through a reputable travel agency. Low fares for flights from mdw to oak are available when booking in advance, with 25 days being an optimal time frame for securing budget-friendly airfares.
What is the cheapest flight from Chicago Midway International to Metropolitan Oakland International?
The cheapest flight from Chicago Midway International to Metropolitan Oakland International can be found on Southwest Airlines (WN) with prices starting from $200.
How far in advance should I book my one-way airfare for the best price?
It is recommended to book your one-way airfare at least 25 days in advance to secure the best prices.
Can I find flights with luxury amenities like fine dining on Milwaukee airlines?
No, luxury amenities like fine dining are not available on Milwaukee Airlines. However, you can consider booking a flight with Southwest Airlines (WN) which offers a luxurious experience with their First cabin.
Are there any discounts or promo codes available for booking flights through agencia website?
Yes, there are discounts and promo codes available for booking flights through the agencia website. You can find these by searching on the website or contacting their customer service.
When is the cheapest time to fly from oak airport to mdw airport?
The cheapest time to fly from oak airport to mdw airport is during the month of November, with prices starting from $150.
How can I ensure I get the lowest fares when searching for airfares on July or December?
To ensure you get the lowest fares when searching for airfares on July or December, it is recommended to book your flight at least 25 days in advance and consider flying on Fridays.
Can I book my flights in advance to secure the best prices and avoid last-minute increases?
Yes, booking your flights in advance can help you secure the best prices and avoid last-minute increases. It is recommended to book at least 25 days in advance for the best deals.

Chicago (MDW) to Oakland (OAK): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Metropolitan Oakland International , Oakland, US
Distance 1844 miles

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