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Cheap flights from Oakland, California to Chicago from $101

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 5/9. 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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0 bags

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Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$201Delta
Mon, Jun 1 - Thu, Jun 4
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$211Delta
Mon, Jun 1 - Thu, Jun 4
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$216Delta
Thu, May 28 - Thu, Jun 4
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
5:41 pm - 11:57 pm
ORD
-
OAK
8h 16m
2 stops
$221Delta
Thu, May 28 - Wed, Jun 3
Alaska Airlines Logo
10:57 am - 1:13 pm
OAK
-
ORD
24h 16m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$257Alaska Airlines
Tue, May 5 - Tue, May 12
Delta Logo
12:34 pm - 9:18 pm
OAK
-
ORD
6h 44m
1 stop
Delta Logo
7:10 pm - 11:54 pm
ORD
-
OAK
6h 44m
1 stop
$261Delta
Sat, Apr 25 - Thu, Apr 30
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
5:57 pm - 11:54 pm
ORD
-
OAK
7h 57m
2 stops
$262Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$266Delta
Sun, May 24 - Thu, Jun 4
Southwest Logo
6:10 am - 6:50 pm
OAK
-
ORD
10h 40m
2 stops
Southwest Logo
7:45 am - 3:30 pm
ORD
-
OAK
9h 45m
2 stops
$267Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
12:55 pm - 10:20 pm
OAK
-
ORD
7h 25m
1 stop
Southwest Logo
7:45 am - 1:30 pm
ORD
-
OAK
7h 45m
1 stop
$271Southwest
Sat, May 2 - Tue, May 5

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
May 5
OAK10:57 amOakland
24h 16m
1 stop
ORD1:13 pmChicago O'Hare Intl
May 12
ORD3:52 pmChicago O'Hare Intl
8h 31m
1 stop
OAK10:23 pmOakland
$257
Alaska Airlines
Jun 20
OAK8:15 pmOakland
15h 06m
1 stop
ORD1:21 pmChicago O'Hare Intl
Jun 23
ORD7:59 pmChicago O'Hare Intl
15h 58m
1 stop
OAK9:57 amOakland
$274
Alaska Airlines
May 6
OAK6:46 amOakland
10h 17m
1 stop
ORD7:03 pmChicago O'Hare Intl
May 13
ORD2:10 pmChicago O'Hare Intl
11h 40m
1 stop
OAK11:50 pmOakland
$280

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

Our best Southwest deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Southwest
May 5
OAK6:10 amOakland
10h 40m
2 stops
ORD6:50 pmChicago O'Hare Intl
May 12
ORD7:45 amChicago O'Hare Intl
9h 45m
2 stops
OAK3:30 pmOakland
$267
Southwest
May 2
OAK12:55 pmOakland
7h 25m
1 stop
ORD10:20 pmChicago O'Hare Intl
May 5
ORD7:45 amChicago O'Hare Intl
7h 45m
1 stop
OAK1:30 pmOakland
$271
Southwest
May 2
OAK5:00 amOakland
7h 30m
1 stop
ORD2:30 pmChicago O'Hare Intl
May 5
ORD7:45 amChicago O'Hare Intl
9h 45m
2 stops
OAK3:30 pmOakland
$276

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 April 9, 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

Mon 6/1

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Thu 6/4

7:45 pm-11:57 pm

1 stop6h 12m

$201

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 6/1

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Thu 6/4

7:45 pm-11:57 pm

1 stop6h 12m

$211

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 5/28

6:00 am-4:29 pm

2 stops8h 29m

Chicago O'Hare Intl

Thu 6/4

7:45 pm-11:57 pm

1 stop6h 12m

$216

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 5/28

6:00 am-4:29 pm

2 stops8h 29m

Chicago O'Hare Intl

Wed 6/3

5:41 pm-11:57 pm

2 stops8h 16m

$221

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/5

10:57 am-1:13 pm

1 stop24h 16m

Chicago O'Hare Intl

Tue 5/12

3:52 pm-10:23 pm

1 stop8h 31m

$257
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 4/25

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Thu 4/30

7:10 pm-11:54 pm

1 stop6h 44m

$261

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 6/2

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Tue 6/9

5:57 pm-11:54 pm

2 stops7h 57m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 5/24

6:00 am-4:29 pm

2 stops8h 29m

Chicago O'Hare Intl

Thu 6/4

7:45 pm-11:57 pm

1 stop6h 12m

$266

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/5

6:10 am-6:50 pm

2 stops10h 40m

Chicago O'Hare Intl

Tue 5/12

7:45 am-3:30 pm

2 stops9h 45m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/2

12:55 pm-10:20 pm

1 stop7h 25m

Chicago O'Hare Intl

Tue 5/5

7:45 am-1:30 pm

1 stop7h 45m

$271

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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $346.

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 $408. 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 $516.

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 $418 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $459. 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 35m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 35m
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 35m 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
Spirit AirlinesPriceFrom $108Free CancellationRating
6.3
8,605 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,557 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $237Free CancellationRating
7.9
12,198 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,337 reviews
Search Southwest 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
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
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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