Cheap Flight Tickets from Chicago (MDW) to Oakland (OAK), Starting at $153

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

$153

WN Southwest Airlines • 1 stop • 13h 40m

Oct 04 – Oct 11

The cheapest round trip flight from Chicago to Oakland (MDW-OAK-MDW) is currently $153

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Cheapest Direct Flight

$178

WN Southwest Airlines • nonstop • 7h 25m

Oct 04

The cheapest nonstop flight from Chicago to Oakland (MDW-OAK) is currently $178

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Fastest Flight

7h 20m

The fastest nonstop flight from Chicago to Oakland (MDW-OAK) takes 7h 20m

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.

Oct 04 - Oct 11, Economy
WN
Chicago → Oakland
13h 40m
10:25 AM - 4:45 PM • 1 stop
WN
Chicago → Oakland
6h 40m
5:10 AM - 11:10 AM • nonstop
$153
Southwest Airlines
Oct 04 - Oct 11, Economy
WN
Chicago → Oakland
10h 40m
8:30 AM - 1:10 PM • 1 stop
WN
Chicago → Oakland
10h 5m
9:45 PM - 5:50 AM • 1 stop
$236
Southwest Airlines
Oct 04 - Oct 11, Economy
WN
Chicago → Oakland
12h 10m
5:10 PM - 10:40 PM • 1 stop
WN
Chicago → Oakland
10h 35m
9:10 PM - 5:45 AM • 1 stop
$626
Southwest Airlines
Oct 04 - Oct 11, Economy
DL
Chicago → Oakland
- • 1 stop
DL
Chicago → Oakland
- • 1 stop
$704
Delta Airlines
Oct 04 - Oct 11, Economy
DL
Chicago → Oakland
- • 1 stop
DL
Chicago → Oakland
- • 1 stop
$937
Delta Airlines
Oct 04 - Oct 11, Economy
F9
Chicago → Oakland
40h 11m
8:23 PM - 6:34 PM • 1 stop
F9
Chicago → Oakland
29h 9m
11:15 PM - 7:04 PM • 1 stop
$1437
Frontier 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 8:30 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 F9 : USD 1437
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 1:1900 pm

Hotels in Oakland (OAK)

5 hotels near Metropolitan Oakland International — compare rates from top booking sites.

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5.0-star hotel 5-star hotel

Claremont Club & Spa - A Fairmont Hotel

📍 41 Tunnel Road, Berkeley, California 94705

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4.5-star hotel 5-star hotel

The Meritage Resort and Spa

📍 875 Bordeaux Way, Napa, California 94558

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4.5-star hotel 5-star hotel

The Rose Hotel

📍 807 Main St, Pleasanton, California 94566

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4.0-star hotel 4-star hotel

Hilton Concord

📍 1970 Diamond Blvd, Concord, California 94520

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4.0-star hotel 4-star hotel

Doubletree By Hilton Lafayette

📍 1521 West Pinkhook Street, Lafayette, California 70503

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Hotel Deals in Oakland (MD)
Owl's Nest

Owl's Nest

9.0/10
★★★★☆
$116/night
View Deal
Oak Mar Motel

Oak Mar Motel

9.5/10
★★★☆☆
✓ Free WiFi
$127/night
View Deal
The Garrett Inn
No chain

The Garrett Inn

9.6/10
★★☆☆☆ Motel
✓ Free WiFi

📍 17848 Garrett Hwy, Oakland (MD)

Check-in 03:00 PM  ·  Check-out 11:00 AM

$153/night
View Deal
Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views!

9.2/10
★★★★★
✓ Free WiFi
$182/night
View Deal
Wild Edges

Wild Edges

7.0/10
★★★★☆
$184/night
View Deal
A214 Studio Standard View

A214 Studio Standard View

8.3/10
★★★★☆
✓ Free WiFi
$185/night
View Deal
A114 One Bedroom Standard View

A114 One Bedroom Standard View

9.1/10
★★★★☆
✓ Free WiFi
$191/night
View Deal
A218 One Bedroom Standard View

A218 One Bedroom Standard View

9.1/10
★★★★☆
✓ Free WiFi
$198/night
View Deal
A304 Studio & Loft Standard View

A304 Studio & Loft Standard View

9.2/10
★★★★☆
✓ Free WiFi
$207/night
View Deal

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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