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Cheap flights from Chicago 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 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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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
6:15 am - 1:40 pmORD-OAK
9h 25m1 stop
Southwest Logo
3:05 pm - 11:40 pmOAK-ORD
6h 35m1 stop
$125Southwest
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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
Spirit Airlines Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
Spirit Airlines Logo
6:00 am - 2:13 pmOAK-ORD
6h 13m1 stop
$128Spirit Airlines
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Wed, Aug 6 - Sat, Aug 9
Southwest Logo
6:15 am - 12:40 pmORD-OAK
8h 25m2 stops
Southwest Logo
3:05 pm - 11:40 pmOAK-ORD
6h 35m1 stop
$130Southwest
Find Deal
Tue, Sep 9 - Sat, Oct 18
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
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Sat, Sep 6 - Tue, Sep 9
Spirit Airlines Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
Spirit Airlines Logo
6:00 am - 2:13 pmOAK-ORD
6h 13m1 stop
$138Spirit Airlines
Find Deal
Tue, Jul 29 - Tue, Aug 12
Alaska Airlines Logo
6:00 am - 12:01 amORD-OAK
20h 01m1 stop
Alaska Airlines Logo
7:00 am - 11:59 pmOAK-ORD
14h 59m1 stop
$182Alaska Airlines
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Thu, Aug 7 - Tue, Aug 12
Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
Logo
8:00 am - 1:07 pmOAK-ORD
27h 07m1 stop
$193
Find Deal
Sat, Aug 9 - Sat, Aug 16
Logo
2:07 pm - 7:18 pmORD-OAK
7h 11m1 stop
Logo
6:00 am - 4:50 amOAK-ORD
20h 50m1 stop
$199
Find Deal
Sat, Aug 23 - Sat, Aug 30

Alaska Airlines flights from Chicago to Oakland, California

Our best Alaska Airlines deals on Chicago to Oakland, California flight tickets
Alaska Airlines
Aug 7
ORD6:00 amChicago O'Hare Intl
20h 01m
1 stop
OAK12:01 amOakland
Aug 12
OAK7:00 amOakland
14h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
$182
Find similar
Alaska Airlines
Jul 19
ORD2:03 pmChicago O'Hare Intl
7h 15m
1 stop
OAK7:18 pmOakland
Jul 23
OAK12:49 pmOakland
7h 41m
1 stop
ORD10:30 pmChicago O'Hare Intl
$401
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Spirit Airlines flights from Chicago to Oakland, California

Our best Spirit Airlines deals on Chicago to Oakland, California flight tickets
Spirit Airlines
Aug 6
ORD3:18 pmChicago O'Hare Intl
10h 15m
1 stop
OAK11:33 pmOakland
Aug 9
OAK6:00 amOakland
6h 13m
1 stop
ORD2:13 pmChicago O'Hare Intl
$128
Find similar
Spirit Airlines
Jul 29
ORD3:18 pmChicago O'Hare Intl
10h 15m
1 stop
OAK11:33 pmOakland
Aug 12
OAK6:00 amOakland
6h 13m
1 stop
ORD2:13 pmChicago O'Hare Intl
$138
Find similar
Spirit Airlines
Aug 8
ORD3:18 pmChicago O'Hare Intl
10h 15m
1 stop
OAK11:33 pmOakland
Aug 12
OAK6:00 amOakland
6h 13m
1 stop
ORD2:13 pmChicago O'Hare Intl
$142
Find similar

See travel insights to San Francisco from

How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Oakland, California?

What is the cheapest month to fly to Oakland, California?

The month of July is, on average, the cheapest month to fly to Oakland, California from Chicago, with most prices found around $247. If you aren’t able to travel to Oakland, California during the month of July, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $300.

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. 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 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 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 to Oakland flight route?

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

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

There are 1 cabin classes available to choose from on Chicago 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 to Oakland, California flights?

You could potentially save up to 24% on your flight if you consider stops on a Chicago to Oakland, California flight.

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

As of July 2025, prices for Chicago to Oakland, California flights are approximately 21% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Oakland, California

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

Cheap Chicago to Oakland, California (CHI to OAK) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago 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 in the past 72 hours is $53. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 hours is $119.
The fastest flight from Chicago to Oakland, California takes 4h 25m
Direct flights go from Chicago to Oakland, California every day.
There is 1 airport near Oakland, California: Oakland (OAK)
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  • How far is Chicago to Oakland by plane?

    Oakland is 1845.3 mi away from Chicago. By plane, this route typically takes 4h 25m.

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

    Prices for flights from Chicago to Oakland Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Chicago 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 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 to Oakland, California?

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

Best airlines flying from Chicago to Oakland, California

Compare and see reviews for airlines that fly from Chicago to Oakland, California with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $127Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $238Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Oakland, California

    Southwest flies from Chicago 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 to Oakland, California in the last 72 hours was $246 (round-trip), much lower than the average airfare cost of $382 for Southwest flights on this route.

Why use momondo?

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

Finding the right flight to Oakland from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Oakland quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Oakland from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Oakland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Oakland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Oakland and let you know when they change.

An easier way to manage your Oakland, California trip

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