Cheap Flight Tickets from Chicago (MDW) to Oakland (OAK), Starting at $484

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

$484

WN Southwest Airlines • nonstop • 7h 5m

Sep 02 – Sep 06

The cheapest round trip flight from Chicago to Oakland (MDW-OAK-MDW) is currently $484

🔍 Search Flights

Cheapest Direct Flight

$484

WN Southwest Airlines • nonstop • 7h 5m

Sep 02

The cheapest nonstop flight from Chicago to Oakland (MDW-OAK) is currently $484

🔍 Search Flights

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

Delta Airline, DL

Delta 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.

Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
7h 5m
10:15 AM - 12:40 PM • nonstop
WN
Chicago → Oakland
6h 40m
11:55 PM - 5:55 AM • nonstop
$484
Southwest Airlines
Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
7h 5m
10:15 AM - 12:40 PM • nonstop
WN
Chicago → Oakland
13h 45m
6:25 AM - 4:50 PM • 1 stop
$494
Southwest Airlines
Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
7h 10m
8:35 PM - 11:05 PM • nonstop
WN
Chicago → Oakland
10h 25m
2:05 PM - 10:30 PM • 1 stop
$494
Southwest Airlines
Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
12h 15m
2:15 PM - 7:50 PM • 1 stop
WN
Chicago → Oakland
6h 40m
7:50 AM - 1:50 PM • nonstop
$494
Southwest Airlines
Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
10h 15m
6:50 AM - 11:05 AM • 1 stop
WN
Chicago → Oakland
6h 40m
11:55 PM - 5:55 AM • nonstop
$494
Southwest Airlines
Sep 02 - Sep 06, Economy
WN
Chicago → Oakland
16h 40m
9:25 AM - 5:25 PM • 1 stop
WN
Chicago → Oakland
6h 40m
11:55 PM - 5:55 AM • nonstop
$494
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 6:50 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 494
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

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

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

More Flight Options for Chicago (MDW) and Oakland (OAK)

Why Fareleaders for MDW to OAK Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Oakland flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to OAK flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Oakland flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Oakland (OAK)
Terms and Conditions*