Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to San Francisco from $80

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 9/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to San Francisco

Cheap round-trip flights

Southwest Logo
3:55 pm - 6:30 pmMDW-OAK
4h 35mnonstop
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$231Southwest
Find Deal
sáb., oct. 4 - mar., oct. 7
Southwest Logo
8:20 am - 1:20 pmMDW-OAK
7h 00m1 stop
Southwest Logo
5:45 am - 3:55 pmOAK-MDW
8h 10m1 stop
$251Southwest
Find Deal
sáb., nov. 1 - mié., nov. 5
Southwest Logo
3:55 pm - 6:30 pmMDW-OAK
4h 35mnonstop
Southwest Logo
8:35 pm - 5:15 amOAK-MDW
6h 40m1 stop
$254Southwest
Find Deal
sáb., oct. 4 - mar., oct. 7
Southwest Logo
5:15 am - 12:05 pmMDW-OAK
8h 50m2 stops
Southwest Logo
2:50 pm - 10:55 pmOAK-MDW
6h 05m1 stop
$256Southwest
Find Deal
sáb., nov. 1 - mié., nov. 5
Southwest Logo
10:55 am - 4:40 pmMDW-OAK
7h 45m1 stop
Southwest Logo
6:45 am - 3:30 pmOAK-MDW
6h 45m1 stop
$264Southwest
Find Deal
mar., oct. 7 - mar., oct. 21
Delta Logo
9:20 am - 4:11 pmMDW-OAK
8h 51m2 stops
Delta Logo
5:55 am - 5:43 pmOAK-MDW
9h 48m2 stops
$267Delta
Find Deal
sáb., nov. 1 - sáb., nov. 8
Southwest Logo
4:15 pm - 6:50 pmMDW-OAK
4h 35mnonstop
Southwest Logo
8:25 pm - 5:05 amOAK-MDW
6h 40m1 stop
$276Southwest
Find Deal
mar., oct. 28 - lun., nov. 3
Southwest Logo
8:40 am - 2:10 pmMDW-OAK
7h 30m1 stop
Southwest Logo
9:40 am - 7:05 pmOAK-MDW
7h 25m1 stop
$277Southwest
Find Deal
mié., sep. 24 - mié., oct. 1
Southwest Logo
5:15 am - 12:05 pmMDW-OAK
8h 50m2 stops
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$282Southwest
Find Deal
sáb., oct. 4 - mar., oct. 7
Southwest Logo
7:45 am - 10:25 amMDW-OAK
4h 40mnonstop
Southwest Logo
9:20 pm - 5:05 amOAK-MDW
5h 45m1 stop
$284Southwest
Find Deal
lun., nov. 24 - lun., dic. 1

Southwest flights from Chicago Midway Airport to Oakland, California

Our best Southwest deals on Chicago Midway Airport to Oakland, California flight tickets
Southwest
Oct 4
MDW3:55 pmChicago Midway
4h 35m
OAK6:30 pmOakland
Oct 7
OAK5:50 amOakland
4h 05m
MDW11:55 amChicago Midway
$231
Find similar
Southwest
Nov 1
MDW8:20 amChicago Midway
7h 00m
1 stop
OAK1:20 pmOakland
Nov 5
OAK5:45 amOakland
8h 10m
1 stop
MDW3:55 pmChicago Midway
$251
Find similar
Southwest
Oct 4
MDW3:55 pmChicago Midway
4h 35m
OAK6:30 pmOakland
Oct 7
OAK8:35 pmOakland
6h 40m
1 stop
MDW5:15 amChicago Midway
$254
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 agosto 27, 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

sáb. 10/4

3:55 pm-6:30 pm

Nonstop4h 35m

Oakland

mar. 10/7

5:50 am-11:55 am

Nonstop4h 05m

$231

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 11/1

8:20 am-1:20 pm

1 stop7h 00m

Oakland

mié. 11/5

5:45 am-3:55 pm

1 stop8h 10m

$251

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 10/4

3:55 pm-6:30 pm

Nonstop4h 35m

Oakland

mar. 10/7

8:35 pm-5:15 am

1 stop6h 40m

$254

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 11/1

5:15 am-12:05 pm

2 stops8h 50m

Oakland

mié. 11/5

2:50 pm-10:55 pm

1 stop6h 05m

$256

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mar. 10/7

10:55 am-4:40 pm

1 stop7h 45m

Oakland

mar. 10/21

6:45 am-3:30 pm

1 stop6h 45m

$264

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 11/1

9:20 am-4:11 pm

2 stops8h 51m

Oakland

sáb. 11/8

5:55 am-5:43 pm

2 stops9h 48m

$267

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mar. 10/28

4:15 pm-6:50 pm

Nonstop4h 35m

Oakland

lun. 11/3

8:25 pm-5:05 am

1 stop6h 40m

$276

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 9/24

8:40 am-2:10 pm

1 stop7h 30m

Oakland

mié. 10/1

9:40 am-7:05 pm

1 stop7h 25m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 10/4

5:15 am-12:05 pm

2 stops8h 50m

Oakland

mar. 10/7

5:50 am-11:55 am

Nonstop4h 05m

$282

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

lun. 11/24

7:45 am-10:25 am

Nonstop4h 40m

Oakland

lun. 12/1

9:20 pm-5:05 am

1 stop5h 45m

$284

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 month to fly to Oakland, California?

The month of November is, on average, the cheapest month to fly to Oakland, California from Chicago Midway Airport, with most prices found around $293. If you aren’t able to travel to Oakland, California during the month of November, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $297.

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

According to our data, Thursday is the cheapest day to fly to Oakland, California from Chicago Midway Airport. The lowest ticket price found for a Thursday departure recently was $383. 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 Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Oakland, California for around $607.

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 $582.

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.

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

As of August 2025, prices for Chicago Midway Airport to Oakland, California flights are approximately 162% more expensive 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

$127

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 $127. The best round-trip flight deal from Chicago Midway Airport to Oakland, California found on momondo in the last 72 hours is $589.
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 30m.

  • 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
4,241 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Oakland, California

    Southwest flies from Chicago Midway Airport to Oakland, California around 17 times per week, with 4,241 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 $372 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.

An easier way to manage your Oakland, California trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
lun. 9/1
lun. 9/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States