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Cheap flights from Chicago Midway Airport to San Francisco from $53

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 8/30. 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

Southwest Logo
6:40 am - 11:10 amMDW-OAK
6h 30m1 stop
Southwest Logo
9:05 am - 3:15 pmOAK-MDW
4h 10mnonstop
$119Southwest
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Tue, Sep 9 - Sat, Oct 18
Southwest Logo
12:55 pm - 7:35 pmMDW-OAK
8h 40m1 stop
Southwest Logo
5:35 am - 1:45 pmOAK-MDW
6h 10m1 stop
$125Southwest
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Sat, Sep 6 - Tue, Sep 9
Southwest Logo
3:20 pm - 8:45 pmMDW-OAK
7h 25m2 stops
Southwest Logo
9:45 am - 7:05 pmOAK-MDW
7h 20m1 stop
$130Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
3:25 pm - 9:00 pmMDW-OAK
7h 35m1 stop
Southwest Logo
11:00 am - 5:05 pmOAK-MDW
4h 05mnonstop
$139Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
12:45 pm - 4:45 pmMDW-OAK
6h 00m1 stop
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$154Southwest
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Tue, Sep 16 - Thu, Oct 23
Southwest Logo
10:00 am - 4:05 pmMDW-OAK
8h 05m2 stops
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$159Southwest
Find Deal
Tue, Sep 16 - Thu, Oct 23
Southwest Logo
1:15 pm - 3:45 pmMDW-OAK
4h 30mnonstop
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$161Southwest
Find Deal
Thu, Sep 25 - Sun, Sep 28
Southwest Logo
6:10 am - 11:55 amMDW-OAK
7h 45m1 stop
Southwest Logo
6:25 am - 3:00 pmOAK-MDW
6h 35m1 stop
$164Southwest
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Wed, Aug 27 - Sat, Aug 30
Logo
12:35 pm - 8:28 amMDW-OAK
21h 53m2 stops
Logo
6:00 am - 12:24 amOAK-MDW
16h 24m2 stops
$303
Find Deal
Mon, Aug 11 - Fri, Aug 22
Logo
6:20 am - 11:33 pmMDW-OAK
19h 13m2 stops
Logo
6:00 am - 2:01 pmOAK-MDW
30h 01m2 stops
$309
Find Deal
Sat, Aug 9 - Tue, Aug 26

Southwest flights from Chicago Midway Airport to Oakland, California

Our best Southwest deals on Chicago Midway Airport to Oakland, California flight tickets
Southwest
Sep 9
MDW6:40 amChicago Midway
6h 30m
1 stop
OAK11:10 amOakland
Oct 18
OAK9:05 amOakland
4h 10m
MDW3:15 pmChicago Midway
$119
Find similar
Southwest
Sep 6
MDW12:55 pmChicago Midway
8h 40m
1 stop
OAK7:35 pmOakland
Sep 9
OAK5:35 amOakland
6h 10m
1 stop
MDW1:45 pmChicago Midway
$125
Find similar
Southwest
Sep 6
MDW3:20 pmChicago Midway
7h 25m
2 stops
OAK8:45 pmOakland
Sep 9
OAK9:45 amOakland
7h 20m
1 stop
MDW7:05 pmChicago Midway
$130
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
Jul 24
MDW9:25 amChicago Midway
16h 30m
2 stops
OAK11:55 pmOakland
Jul 28
OAK4:55 pmOakland
13h 49m
2 stops
MDW8:44 amChicago Midway
$486
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Delta
Jul 24
MDW9:25 amChicago Midway
16h 30m
2 stops
OAK11:55 pmOakland
Jul 31
OAK4:55 pmOakland
13h 49m
2 stops
MDW8:44 amChicago Midway
$531
Find similar
Delta
Jul 23
MDW9:25 amChicago Midway
16h 30m
2 stops
OAK11:55 pmOakland
Jul 28
OAK4:55 pmOakland
13h 49m
2 stops
MDW8:44 amChicago Midway
$542
Find similar

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, 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 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 $541.

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 $337. 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 $546.

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 are 1 cabin classes 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 July 2025, prices for Chicago Midway Airport to Oakland, California flights are approximately 45% 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

$53

Fastest flight time

4h 25m

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 $53. The best round-trip flight deal from Chicago Midway Airport to Oakland, California found on momondo in the last 72 hours is $119.
The fastest flight from Chicago Midway Airport to Oakland, California takes 4h 25m
Direct flights go from Chicago Midway Airport to Oakland, California every day.
There is 1 airport near Oakland, California: Oakland (OAK)
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  • 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 25m.

  • 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
4,249 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Oakland, California

    Southwest flies from Chicago Midway Airport to Oakland, California around 10 times per week, with 4,249 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 $368 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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