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Cheap flights from Chicago to Oakland, California from $65

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 Oakland, California departing on 1/28. 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 to San Francisco

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to San Francisco that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San Francisco.

Cheap last minute flights

Planning a quick getaway from Chicago to San Francisco? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Francisco, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San Francisco

Find recent round-trip train or bus tickets from Chicago to San Francisco.

All round-trip flight deals to San Francisco

The cheapest plane tickets to San Francisco found on KAYAK recently.
8:00 am - 9:35 pmORD-OAK
15h 35m1 stop
7:02 pm - 5:31 amOAK-ORD
8h 29m1 stop
$131Spirit Airlines
Find Deal
Sat, Jan 25 - Tue, Jan 28
8:00 am - 9:35 pmORD-OAK
15h 35m1 stop
7:02 pm - 5:31 amOAK-ORD
8h 29m1 stop
$133Spirit Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
8:00 am - 11:36 pmORD-OAK
17h 36m1 stop
5:10 am - 1:01 amOAK-ORD
17h 51m2 stops
Sat, Feb 8 - Sat, Feb 15
10:47 pm - 6:47 amORD-OAK
10h 00m1 stop
5:10 am - 1:01 amOAK-ORD
17h 51m2 stops
Sat, Feb 8 - Sat, Feb 15
1:40 pm - 11:56 pmORD-OAK
12h 16m2 stops
6:00 am - 5:29 pmOAK-ORD
9h 29m2 stops
$266Delta
Find Deal
Tue, Jan 28 - Sat, Feb 1
9:15 am - 2:35 pmMDW-OAK
7h 20m1 stop
6:25 am - 3:40 pmOAK-MDW
7h 15m1 stop
$267Southwest
Find Deal
Wed, Jan 29 - Mon, Feb 3
9:15 am - 2:35 pmMDW-OAK
7h 20m1 stop
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
$271Southwest
Find Deal
Wed, Jan 29 - Mon, Feb 3
2:07 pm - 10:39 pmORD-OAK
10h 32m1 stop
9:46 am - 11:59 pmOAK-ORD
12h 13m2 stops
$279Alaska Airlines
Find Deal
Thu, Jan 23 - Thu, Jan 30
6:55 pm - 9:06 amORD-OAK
16h 11m1 stop
7:32 pm - 11:59 pmOAK-ORD
26h 27m1 stop
$293Alaska Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
5:00 pm - 10:54 pmORD-OAK
7h 54m1 stop
6:00 am - 1:47 pmOAK-ORD
5h 47m1 stop
$304Delta
Find Deal
Sat, Jan 11 - Thu, Jan 16
1:39 pm - 9:35 pmORD-OAK
9h 56m1 stop
$65Spirit Airlines
Find Deal
Tue, Jan 28
9:54 pm - 6:47 amORD-OAK
10h 53m1 stop
$75Spirit Airlines
Find Deal
Wed, Jan 8
5:10 pm - 8:00 pmMDW-OAK
4h 50mnonstop
$99Southwest
Find Deal
Sat, Feb 15
6:20 pm - 9:15 pmMDW-OAK
4h 55mnonstop
$109Southwest
Find Deal
Fri, Feb 28
4:05 pm - 8:44 amORD-OAK
18h 39m1 stop
$114Alaska Airlines
Find Deal
Wed, Mar 12
1:26 pm - 11:56 pmMDW-OAK
12h 30m2 stops
$133Delta
Find Deal
Fri, Jan 24
5:00 pm - 11:56 pmORD-OAK
8h 56m1 stop
$151Delta
Find Deal
Wed, Jan 8
7:45 am - 1:41 pmORD-OAK
7h 56m1 stop
$173Alaska Airlines
Find Deal
Thu, Feb 6
11:45 am - 9:24 amORD-OAK
23h 39m3 stops
Sun, Mar 30
4:23 pm - 2:10 pmORD-OAK
23h 47m3 stops
Mon, Mar 10
9:54 pm - 9:29 amORD-OAK
13h 35m1 stop
7:42 am - 9:52 pmOAK-ORD
12h 10m1 stop
$485Spirit Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 11
4:00 pm - 11:13 pmORD-OAK
9h 13m1 stop
1:15 pm - 9:22 pmOAK-ORD
6h 07m1 stop
$490Delta
Find Deal
Tue, Dec 31 - Thu, Jan 9
3:10 pm - 8:25 pmORD-OAK
7h 15m1 stop
2:50 pm - 10:35 pmOAK-ORD
5h 45m1 stop
$513Southwest
Find Deal
Sun, Dec 29 - Tue, Dec 31
3:10 pm - 10:35 pmORD-OAK
9h 25m2 stops
2:50 pm - 10:35 pmOAK-ORD
5h 45m1 stop
$518Southwest
Find Deal
Sun, Dec 29 - Tue, Dec 31
3:10 pm - 10:35 pmORD-OAK
9h 25m2 stops
1:10 pm - 11:05 pmOAK-ORD
7h 55m2 stops
$538Southwest
Find Deal
Sun, Dec 29 - Tue, Dec 31
9:54 pm - 9:43 amORD-OAK
13h 49m1 stop
6:36 pm - 5:30 amOAK-ORD
8h 54m1 stop
$560Spirit Airlines
Find Deal
Mon, Dec 30 - Wed, Jan 1
9:54 pm - 9:43 amORD-OAK
13h 49m1 stop
6:36 pm - 5:30 amOAK-ORD
8h 54m1 stop
$596Spirit Airlines
Find Deal
Tue, Dec 31 - Thu, Jan 2
4:00 pm - 11:13 pmORD-OAK
9h 13m1 stop
1:15 pm - 9:22 pmOAK-ORD
6h 07m1 stop
$610Delta
Find Deal
Tue, Dec 31 - Fri, Jan 10
5:50 pm - 11:59 pmORD-OAK
8h 09m1 stop
6:00 am - 6:10 pmOAK-ORD
10h 10m1 stop
$703Alaska Airlines
Find Deal
Fri, Dec 27 - Sat, Jan 4
8:00 am - 2:40 pmORD-OAK
8h 40m1 stop
6:00 am - 4:50 pmOAK-ORD
8h 50m1 stop
$802Alaska Airlines
Find Deal
Fri, Dec 27 - Sat, Jan 4
4:25 pm - 7:15 pmMDW-OAK
4h 50mnonstop
11:25 am - 5:30 pmOAK-MDW
4h 05mnonstop
$283Southwest
Find Deal
Fri, Feb 7 - Mon, Feb 10
9:40 am - 12:35 pmMDW-OAK
4h 55mnonstop
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
$321Southwest
Find Deal
Wed, Jan 29 - Mon, Feb 3
9:40 am - 12:35 pmMDW-OAK
4h 55mnonstop
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
$454Southwest
Find Deal
Fri, Jan 10 - Tue, Jan 14
5:10 pm - 7:55 pmMDW-OAK
4h 45mnonstop
11:25 am - 5:30 pmOAK-MDW
4h 05mnonstop
$459Southwest
Find Deal
Mon, Jan 6 - Thu, Jan 16
1:35 pm - 4:20 pmMDW-OAK
4h 45mnonstop
2:40 pm - 8:40 pmOAK-MDW
4h 00mnonstop
$763Southwest
Find Deal
Sun, Mar 23 - Sat, Mar 29

Southwest flights from Chicago to Oakland, California

Our best Southwest deals on Chicago to Oakland, California flight tickets
Southwest
Jan 29
MDW9:15 amChicago Midway
7h 20m
1 stop
OAK2:35 pmOakland
Feb 3
OAK6:25 amOakland
7h 15m
1 stop
MDW3:40 pmChicago Midway
Southwest
Jan 29
MDW9:15 amChicago Midway
7h 20m
1 stop
OAK2:35 pmOakland
Feb 3
OAK11:05 amOakland
4h 05m
MDW5:10 pmChicago Midway
Southwest
Feb 7
MDW4:25 pmChicago Midway
4h 50m
OAK7:15 pmOakland
Feb 10
OAK11:25 amOakland
4h 05m
MDW5:30 pmChicago Midway

Spirit Airlines flights from Chicago to Oakland, California

Our best Spirit Airlines deals on Chicago to Oakland, California flight tickets
Spirit Airlines
Jan 25
ORD8:00 amChicago O'Hare Intl
15h 35m
1 stop
OAK9:35 pmOakland
Jan 28
OAK7:02 pmOakland
8h 29m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Feb 1
ORD8:00 amChicago O'Hare Intl
15h 35m
1 stop
OAK9:35 pmOakland
Feb 8
OAK7:02 pmOakland
8h 29m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Jan 30
ORD10:47 pmChicago O'Hare Intl
10h 00m
1 stop
OAK6:47 amOakland
Feb 1
OAK7:02 pmOakland
8h 29m
1 stop
ORD5:31 amChicago O'Hare Intl

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 $240. If you aren’t able to travel to Oakland, California during the month of July, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $283.

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

According to our data, Wednesday is the cheapest day to fly to Oakland, California from Chicago. The lowest ticket price found for a Wednesday departure recently was $255. 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 Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Oakland, California for around $425.

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

In the afternoon is the cheapest time of day to fly from Chicago to Oakland, California when you can find flight prices for as low as $276. Flying to Oakland, California in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the evening are often more expensive with an average ticket price of $364.

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 34% 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 December 2024, prices for Chicago to Oakland, California flights are approximately 39% more expensive 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

$65

Fastest flight time

4h 35m

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 $65. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 hours is $131.
The fastest flight from Chicago to Oakland, California takes 4h 35m
Direct flights go from Chicago to Oakland, California every day.
There is 1 airport near Oakland, California: Oakland (OAK)

  • How far is Chicago to Oakland by plane?

    Oakland is 1845.3 mi away from Chicago. By plane, this route typically takes 4h 35m.

  • 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 $133Free CancellationRating
6.3
8,103 reviews
Search Spirit Airlines flights
DeltaPriceFrom $235Free CancellationRating
8.0
8,580 reviews
Search Delta flights
Alaska AirlinesPriceFrom $236Free CancellationRating
8.0
9,553 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $242Free CancellationRating
8.1
4,752 reviews
Search Southwest flights
  • Southwest Flights From Chicago to Oakland, California

    Southwest flies from Chicago to Oakland, California around 14 times per week, with 4,752 momondo users rating the airline 8.1/10. The cheapest Southwest deal from Chicago to Oakland, California in the last 72 hours was $242 (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?

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.


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