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Cheap flights from Chicago Midway Airport to San Francisco from $130

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Francisco departing on 3/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San Francisco

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:35 pm - 10:15 pm
MDW
-
OAK
6h 40m1 stop
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
$277Southwest
Fri, Jan 30 - Tue, Feb 3
Southwest Logo
11:10 am - 2:05 pm
MDW
-
OAK
4h 55mnonstop
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
$279Southwest
Fri, Jan 23 - Sun, Jan 25
Southwest Logo
5:35 pm - 10:15 pm
MDW
-
OAK
6h 40m1 stop
Southwest Logo
6:25 am - 4:05 pm
OAK
-
MDW
7h 40m1 stop
$287Southwest
Fri, Jan 30 - Tue, Feb 3
Southwest Logo
7:55 am - 12:35 pm
MDW
-
OAK
6h 40m1 stop
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
$289Southwest
Sun, Jan 11 - Thu, Jan 15
Southwest Logo
5:55 am - 11:15 am
MDW
-
OAK
7h 20m1 stop
Southwest Logo
7:00 am - 4:45 pm
OAK
-
MDW
7h 45m2 stops
$292Southwest
Fri, Jan 30 - Tue, Feb 3
Southwest Logo
8:10 am - 2:55 pm
MDW
-
OAK
8h 45m2 stops
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
$294Southwest
Fri, Jan 23 - Sun, Jan 25
Southwest Logo
7:55 am - 12:35 pm
MDW
-
OAK
6h 40m1 stop
Southwest Logo
8:20 am - 5:10 pm
OAK
-
MDW
6h 50m1 stop
$299Southwest
Sun, Jan 11 - Thu, Jan 15
Southwest Logo
7:55 am - 12:35 pm
MDW
-
OAK
6h 40m1 stop
Southwest Logo
10:40 am - 9:05 pm
OAK
-
MDW
8h 25m2 stops
$304Southwest
Sun, Jan 11 - Thu, Jan 15
Southwest Logo
7:55 am - 10:50 am
MDW
-
OAK
4h 55mnonstop
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
$306Southwest
Fri, Feb 13 - Sun, Feb 15
Southwest Logo
1:45 pm - 8:15 pm
MDW
-
OAK
8h 30m1 stop
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
$325Southwest
Fri, Jan 16 - Mon, Jan 19

Southwest flights from Chicago Midway Airport to Oakland, California

Our best Southwest deals on Chicago Midway Airport to Oakland, California flight tickets
Southwest
Jan 30
MDW5:35 pmChicago Midway
6h 40m
1 stop
OAK10:15 pmOakland
Feb 3
OAK11:10 amOakland
4h 05m
MDW5:15 pmChicago Midway
$277
Find similar
Southwest
Jan 23
MDW11:10 amChicago Midway
4h 55m
OAK2:05 pmOakland
Jan 25
OAK6:30 amOakland
4h 05m
MDW12:35 pmChicago Midway
$279
Find similar
Southwest
Jan 30
MDW5:35 pmChicago Midway
6h 40m
1 stop
OAK10:15 pmOakland
Feb 3
OAK6:25 amOakland
7h 40m
1 stop
MDW4:05 pmChicago Midway
$287
Find similar

Delta flights from Chicago Midway Airport to Oakland, California

Our best Delta deals on Chicago Midway Airport to Oakland, California flight tickets
Delta
Dec 9
MDW1:50 pmChicago Midway
12h 18m
2 stops
OAK12:08 amOakland
Dec 15
OAK5:55 amOakland
10h 23m
2 stops
MDW6:18 pmChicago Midway
$593
Find similar
Delta
Dec 9
MDW1:50 pmChicago Midway
12h 18m
2 stops
OAK12:08 amOakland
Dec 13
OAK5:55 amOakland
10h 23m
2 stops
MDW6:18 pmChicago Midway
$699
Find similar
Delta
Dec 9
MDW1:50 pmChicago Midway
12h 18m
2 stops
OAK12:08 amOakland
Dec 12
OAK5:55 amOakland
10h 23m
2 stops
MDW6:18 pmChicago Midway
$989
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Oakland, California that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Oakland, California that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/30

5:35 pm-10:15 pm

1 stop6h 40m

Oakland

Tue 2/3

11:10 am-5:15 pm

Nonstop4h 05m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/23

11:10 am-2:05 pm

Nonstop4h 55m

Oakland

Sun 1/25

6:30 am-12:35 pm

Nonstop4h 05m

$279

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/30

5:35 pm-10:15 pm

1 stop6h 40m

Oakland

Tue 2/3

6:25 am-4:05 pm

1 stop7h 40m

$287

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/11

7:55 am-12:35 pm

1 stop6h 40m

Oakland

Thu 1/15

6:30 am-12:35 pm

Nonstop4h 05m

$289

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/30

5:55 am-11:15 am

1 stop7h 20m

Oakland

Tue 2/3

7:00 am-4:45 pm

2 stops7h 45m

$292

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/23

8:10 am-2:55 pm

2 stops8h 45m

Oakland

Sun 1/25

6:30 am-12:35 pm

Nonstop4h 05m

$294

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/11

7:55 am-12:35 pm

1 stop6h 40m

Oakland

Thu 1/15

8:20 am-5:10 pm

1 stop6h 50m

$299

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/11

7:55 am-12:35 pm

1 stop6h 40m

Oakland

Thu 1/15

10:40 am-9:05 pm

2 stops8h 25m

$304

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 2/13

7:55 am-10:50 am

Nonstop4h 55m

Oakland

Sun 2/15

6:30 am-12:35 pm

Nonstop4h 05m

$306

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/16

1:45 pm-8:15 pm

1 stop8h 30m

Oakland

Mon 1/19

6:30 am-12:35 pm

Nonstop4h 05m

$325

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Francisco from

How to get the cheapest flight ticket from Chicago Midway Airport to Oakland, California

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Oakland, California?

According to our data, Monday is the cheapest day to fly to Oakland, California from Chicago Midway Airport. The lowest ticket price found for a Monday departure recently was $337. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Oakland, California for around $617.

What is the cheapest time of day to depart on your flight to Oakland, California?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Oakland, California when you can find flight prices for as low as $354. Flying to Oakland, California at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $613.

What is the cheapest Chicago Midway to Oakland flight route?

Fly from Chicago Midway to Oakland for the best Chicago Midway - Oakland flight prices

What cabin class options are available on Chicago Midway to Oakland flights?

There is only 1 cabin class available to choose from on Chicago Midway to Oakland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Oakland, California flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Oakland, California.

How have Chicago Midway Airport to Oakland, California flight prices changed over time?

As of December 2025, prices for Chicago Midway Airport to Oakland, California flights are approximately 22% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Oakland, California

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Oakland, California according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Oakland, California (MDW to OAK) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Oakland, California

Best Price Found

$323

Fastest flight time

4h 30m

Direct flights

Every day

Airports in Oakland, California

1 airport
The best one-way flight to Oakland, California from Chicago Midway Airport in the past 72 hours is $323. The best round-trip flight deal from Chicago Midway Airport to Oakland, California found on momondo in the last 72 hours is $492.
The fastest flight from Chicago Midway Airport to Oakland, California takes 4h 30m
Direct flights go from Chicago Midway Airport to Oakland, California every day.
There is 1 airport near Oakland, California: Oakland (OAK)
Search flight deals

  • How far is Chicago Midway to Oakland by plane?

    The distance between Chicago Midway and Oakland is about 1839.5 mi. By plane, this route typically takes 4h 35m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Oakland Airport?

    Prices for flights from Chicago Midway Airport to Oakland Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Oakland Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Oakland Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Oakland Airport.

  • What documentation or ID do you need to fly to Oakland Airport?

    The travel and health documents required for your trip to Oakland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oakland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to Oakland, California?

  • What is the most popular airline from Chicago Midway Airport to Oakland, California?

Best airlines flying from Chicago Midway Airport to Oakland, California

Compare and see reviews for airlines that fly from Chicago Midway Airport to Oakland, California with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $247Free CancellationRating
8.0
4,252 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Oakland, California

    Southwest flies from Chicago Midway Airport to Oakland, California around 8 times per week, with 4,252 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Oakland, California in the last 72 hours was $247 (round-trip), much lower than the average airfare cost of $443 for Southwest flights on this route.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Oakland?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Oakland. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Oakland with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Oakland flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Oakland?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Oakland.

I’m not ready to book a flight from Chicago to Oakland right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Oakland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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