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Cheap flights from Chicago Midway Airport to San Francisco from $117

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 2/14. 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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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
4:05 pm - 6:40 pmMDW-OAK
4h 35mnonstop
Southwest Logo
5:55 am - 12:00 pmOAK-MDW
4h 05mnonstop
$301Southwest
Find Deal
Mon, Dec 15 - Sat, Jan 10
Southwest Logo
5:25 am - 11:15 amMDW-OAK
7h 50m1 stop
Southwest Logo
10:15 am - 4:20 pmOAK-MDW
4h 05mnonstop
$309Southwest
Find Deal
Tue, Nov 11 - Sat, Nov 15
Southwest Logo
4:05 pm - 6:40 pmMDW-OAK
4h 35mnonstop
Southwest Logo
5:25 am - 11:30 amOAK-MDW
4h 05mnonstop
$311Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Southwest Logo
4:05 pm - 6:40 pmMDW-OAK
4h 35mnonstop
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
$313Southwest
Find Deal
Mon, Dec 15 - Fri, Jan 9
Southwest Logo
12:05 pm - 6:20 pmMDW-OAK
8h 15m2 stops
Southwest Logo
10:15 am - 4:20 pmOAK-MDW
4h 05mnonstop
$314Southwest
Find Deal
Tue, Nov 11 - Sat, Nov 15
Southwest Logo
10:05 am - 4:00 pmMDW-OAK
7h 55m1 stop
Southwest Logo
8:00 pm - 5:15 amOAK-MDW
7h 15m1 stop
$319Southwest
Find Deal
Wed, Nov 19 - Wed, Nov 26
Southwest Logo
5:25 am - 11:15 amMDW-OAK
7h 50m1 stop
Southwest Logo
5:25 am - 11:30 amOAK-MDW
4h 05mnonstop
$321Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Southwest Logo
7:45 am - 10:25 amMDW-OAK
4h 40mnonstop
Southwest Logo
7:50 am - 3:25 pmOAK-MDW
5h 35m1 stop
$323Southwest
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
1:15 pm - 12:03 amMDW-OAK
12h 48m2 stops
Delta Logo
5:55 am - 6:08 pmOAK-MDW
10h 13m2 stops
$329Delta
Find Deal
Tue, Nov 11 - Sat, Nov 15
Delta Logo
1:26 pm - 9:39 pmMDW-OAK
10h 13m2 stops
Delta Logo
4:51 pm - 9:52 amOAK-MDW
15h 01m2 stops
$331Delta
Find Deal
Sat, Nov 15 - Mon, Nov 17

Southwest flights from Chicago Midway Airport to Oakland, California

Our best Southwest deals on Chicago Midway Airport to Oakland, California flight tickets
Southwest
Dec 15
MDW4:05 pmChicago Midway
4h 35m
OAK6:40 pmOakland
Jan 10
OAK5:55 amOakland
4h 05m
MDW12:00 pmChicago Midway
$301
Find similar
Southwest
Nov 11
MDW5:25 amChicago Midway
7h 50m
1 stop
OAK11:15 amOakland
Nov 15
OAK10:15 amOakland
4h 05m
MDW4:20 pmChicago Midway
$309
Find similar
Southwest
Nov 12
MDW4:05 pmChicago Midway
4h 35m
OAK6:40 pmOakland
Nov 16
OAK5:25 amOakland
4h 05m
MDW11:30 amChicago Midway
$311
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
Nov 11
MDW1:15 pmChicago Midway
12h 48m
2 stops
OAK12:03 amOakland
Nov 15
OAK5:55 amOakland
10h 13m
2 stops
MDW6:08 pmChicago Midway
$329
Find similar
Delta
Nov 15
MDW1:26 pmChicago Midway
10h 13m
2 stops
OAK9:39 pmOakland
Nov 17
OAK4:51 pmOakland
15h 01m
2 stops
MDW9:52 amChicago Midway
$331
Find similar
Delta
Nov 14
MDW1:15 pmChicago Midway
12h 48m
2 stops
OAK12:03 amOakland
Nov 15
OAK5:55 amOakland
10h 23m
2 stops
MDW6:18 pmChicago Midway
$339
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 October 14, 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

Mon 12/15

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Sat 1/10

5:55 am-12:00 pm

Nonstop4h 05m

$301

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 11/11

5:25 am-11:15 am

1 stop7h 50m

Oakland

Sat 11/15

10:15 am-4:20 pm

Nonstop4h 05m

$309

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 11/12

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Sun 11/16

5:25 am-11:30 am

Nonstop4h 05m

$311

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 12/15

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Fri 1/9

11:10 am-5:15 pm

Nonstop4h 05m

$313

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 11/11

12:05 pm-6:20 pm

2 stops8h 15m

Oakland

Sat 11/15

10:15 am-4:20 pm

Nonstop4h 05m

$314

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 11/19

10:05 am-4:00 pm

1 stop7h 55m

Oakland

Wed 11/26

8:00 pm-5:15 am

1 stop7h 15m

$319

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 11/11

5:25 am-11:15 am

1 stop7h 50m

Oakland

Fri 11/14

5:25 am-11:30 am

Nonstop4h 05m

$321

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 11/14

7:45 am-10:25 am

Nonstop4h 40m

Oakland

Mon 11/17

7:50 am-3:25 pm

1 stop5h 35m

$323

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 11/11

1:15 pm-12:03 am

2 stops12h 48m

Oakland

Sat 11/15

5:55 am-6:08 pm

2 stops10h 13m

$329

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 11/15

1:26 pm-9:39 pm

2 stops10h 13m

Oakland

Mon 11/17

4:51 pm-9:52 am

2 stops15h 01m

$331

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $382. 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 $610.

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 $609.

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 October 2025, prices for Chicago Midway Airport to Oakland, California flights are approximately 234% 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

$249

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 $249. The best round-trip flight deal from Chicago Midway Airport to Oakland, California found on momondo in the last 72 hours is $562.
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
4,238 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Oakland, California

    Southwest flies from Chicago Midway Airport to Oakland, California around 15 times per week, with 4,238 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 $387 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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