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Cheap flights from Oakland, California to Chicago from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Chicago departing on 8/4. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
10:37 am - 7:37 pm
OAK
-
ORD
7h 00m
1 stop
Alaska Airlines Logo
2:18 pm - 9:28 pm
ORD
-
OAK
9h 10m
1 stop
$257Alaska Airlines
Sat, Aug 15 - Wed, Aug 26
Delta Logo
12:31 pm - 10:00 pm
OAK
-
ORD
7h 29m
1 stop
Delta Logo
7:30 pm - 11:56 pm
ORD
-
OAK
6h 26m
1 stop
$265Delta
Sat, Oct 17 - Mon, Oct 26
Delta Logo
12:31 pm - 10:00 pm
OAK
-
ORD
7h 29m
1 stop
Delta Logo
2:00 pm - 11:56 pm
ORD
-
OAK
11h 56m
2 stops
$270Delta
Sat, Oct 17 - Thu, Oct 22
Alaska Airlines Logo
1:29 pm - 11:59 pm
OAK
-
ORD
8h 30m
1 stop
Alaska Airlines Logo
2:18 pm - 9:28 pm
ORD
-
OAK
9h 10m
1 stop
$273Alaska Airlines
Mon, Sep 28 - Wed, Sep 30
Delta Logo
5:00 pm - 9:23 am
OAK
-
ORD
14h 23m
2 stops
Delta Logo
1:59 pm - 11:56 pm
ORD
-
OAK
11h 57m
2 stops
$275Delta
Tue, Aug 11 - Tue, Aug 18
Multiple Airlines Logo
12:13 pm - 7:02 pm
OAK
-
ORD
28h 49m
1 stop
Multiple Airlines Logo
2:18 pm - 9:28 pm
ORD
-
OAK
9h 10m
1 stop
$279Multiple Airlines
Wed, Aug 26 - Tue, Sep 1
Frontier Logo
8:39 pm - 5:42 am
OAK
-
ORD
7h 03m
1 stop
Frontier Logo
6:50 am - 11:18 am
ORD
-
OAK
6h 28m
1 stop
$281Frontier
Thu, Oct 15 - Sun, Oct 18
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:01 am - 11:06 am
ORD
-
OAK
7h 05m
1 stop
$289Alaska Airlines
Thu, Aug 13 - Thu, Aug 20
Alaska Airlines Logo
7:52 am - 5:00 am
OAK
-
ORD
19h 08m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$297Alaska Airlines
Wed, Jul 22 - Wed, Jul 29
Alaska Airlines Logo
7:13 pm - 5:00 am
OAK
-
ORD
7h 47m
1 stop
Alaska Airlines Logo
6:20 am - 2:10 pm
ORD
-
OAK
9h 50m
1 stop
$306Alaska Airlines
Mon, Jul 20 - Wed, Jul 29

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Delta flights from Oakland, California to Chicago O'Hare Intl Airport

Our best Delta deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Delta
Oct 17
OAK12:31 pmOakland
7h 29m
1 stop
ORD10:00 pmChicago O'Hare Intl
Oct 22
ORD7:30 pmChicago O'Hare Intl
6h 26m
1 stop
OAK11:56 pmOakland
$265
Delta
Oct 17
OAK12:31 pmOakland
7h 29m
1 stop
ORD10:00 pmChicago O'Hare Intl
Oct 24
ORD5:30 amChicago O'Hare Intl
12h 53m
2 stops
OAK4:23 pmOakland
$270
Delta
Aug 11
OAK5:00 pmOakland
14h 23m
2 stops
ORD9:23 amChicago O'Hare Intl
Aug 18
ORD1:59 pmChicago O'Hare Intl
11h 57m
2 stops
OAK11:56 pmOakland
$275

Alaska Airlines flights from Oakland, California to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Aug 15
OAK10:37 amOakland
7h 00m
1 stop
ORD7:37 pmChicago O'Hare Intl
Aug 26
ORD2:18 pmChicago O'Hare Intl
9h 10m
1 stop
OAK9:28 pmOakland
$257
Alaska Airlines
Sep 28
OAK1:29 pmOakland
8h 30m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 29
ORD2:18 pmChicago O'Hare Intl
9h 10m
1 stop
OAK9:28 pmOakland
$273
Alaska Airlines
Aug 13
OAK2:50 pmOakland
6h 46m
1 stop
ORD11:36 pmChicago O'Hare Intl
Aug 20
ORD6:01 amChicago O'Hare Intl
7h 05m
1 stop
OAK11:06 amOakland
$289

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California to Chicago O'Hare Intl Airport 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 June 29, 2026.
Use the filters below to find and compare flights from Oakland, California to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 8/15

10:37 am-7:37 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 8/26

2:18 pm-9:28 pm

1 stop9h 10m

$257

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 10/17

12:31 pm-10:00 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 10/26

7:30 pm-11:56 pm

1 stop6h 26m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 10/17

12:31 pm-10:00 pm

1 stop7h 29m

Chicago O'Hare Intl

Thu 10/22

2:00 pm-11:56 pm

2 stops11h 56m

$270

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 9/28

1:29 pm-11:59 pm

1 stop8h 30m

Chicago O'Hare Intl

Wed 9/30

2:18 pm-9:28 pm

1 stop9h 10m

$273

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 8/11

5:00 pm-9:23 am

2 stops14h 23m

Chicago O'Hare Intl

Tue 8/18

1:59 pm-11:56 pm

2 stops11h 57m

$275

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 8/26

12:13 pm-7:02 pm

1 stop28h 49m

Chicago O'Hare Intl

Tue 9/1

2:18 pm-9:28 pm

1 stop9h 10m

$279
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 10/15

8:39 pm-5:42 am

1 stop7h 03m

Chicago O'Hare Intl

Sun 10/18

6:50 am-11:18 am

1 stop6h 28m

$281

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 8/13

2:50 pm-11:36 pm

1 stop6h 46m

Chicago O'Hare Intl

Thu 8/20

6:01 am-11:06 am

1 stop7h 05m

$289

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 7/22

7:52 am-5:00 am

1 stop19h 08m

Chicago O'Hare Intl

Wed 7/29

7:59 pm-9:57 am

1 stop15h 58m

$297

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 7/20

7:13 pm-5:00 am

1 stop7h 47m

Chicago O'Hare Intl

Wed 7/29

6:20 am-2:10 pm

1 stop9h 50m

$306

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Oakland, California to Chicago O'Hare Intl Airport

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 Oakland, California and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $358.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $441. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Oakland, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $561.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Oakland, California in the evening is the least expensive time of day to depart. momondo users have found prices as low as $459 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $498. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Oakland, California to Chicago O'Hare Intl Airport flights?

You could potentially save up to 3% on your flight if you consider stops on a Oakland, California to Chicago O'Hare Intl Airport flight.

How have Oakland, California to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Oakland, California to Chicago O'Hare Intl Airport

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

Cheap Oakland, California to Chicago O'Hare Intl Airport (OAK to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago O'Hare Intl Airport

Fastest flight time

6h 29m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 29m
There are no direct flights from Oakland, California to Chicago O'Hare Intl Airport. There are no popular flight routes from Oakland, California to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Oakland, California to Chicago O'Hare Intl Airport

  • How far is Oakland to Chicago O'Hare Intl by plane?

    The distance between Oakland and Chicago O'Hare Intl is about 1830.7 mi. Typically, this will take 6h 29m by plane in normal conditions.

  • When did momondo last update prices for flights from Oakland Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Oakland Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Oakland Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Oakland Airport to Chicago O'Hare Intl 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 Oakland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl 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 Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Oakland, California to Chicago O'Hare Intl Airport?

Best airlines flying from Oakland, California to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Oakland, California to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,896 reviews
Search United Airlines flights
SouthwestPriceFrom $252Free CancellationRating
7.9
4,246 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $272Free CancellationRating
7.9
12,590 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

Why use momondo?

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

It is quick and easy to find Oakland to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for Oakland to Chicago flights to just show those with flexible booking policies.

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

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 Oakland to Chicago.

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

Yes. momondo can track prices for Oakland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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