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Cheap flights from Oakland, California to Chicago from $122

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 10/22. 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.
Frontier Logo
12:13 pm - 5:42 am
OAK
-
ORD
15h 29m
1 stop
Frontier Logo
2:46 pm - 11:18 am
ORD
-
OAK
22h 32m
2 stops
$232Frontier
Wed, Sep 9 - Tue, Sep 15
Frontier Logo
12:13 pm - 5:42 am
OAK
-
ORD
15h 29m
1 stop
Frontier Logo
2:46 pm - 11:18 am
ORD
-
OAK
22h 32m
2 stops
$236Frontier
Wed, Sep 9 - Mon, Sep 14
Frontier Logo
8:39 pm - 11:57 am
OAK
-
ORD
13h 18m
1 stop
Frontier Logo
6:50 am - 11:18 am
ORD
-
OAK
6h 28m
1 stop
$244Frontier
Thu, Sep 10 - Sat, Sep 12
Frontier Logo
8:37 pm - 7:02 pm
OAK
-
ORD
20h 25m
1 stop
Frontier Logo
6:50 am - 7:44 pm
ORD
-
OAK
14h 54m
1 stop
$246Frontier
Thu, Sep 3 - Thu, Sep 10
Frontier Logo
12:13 pm - 5:42 am
OAK
-
ORD
15h 29m
1 stop
Frontier Logo
6:50 am - 11:18 am
ORD
-
OAK
30h 28m
1 stop
$247Frontier
Wed, Sep 9 - Tue, Sep 15
Frontier Logo
8:39 pm - 11:57 am
OAK
-
ORD
13h 18m
1 stop
Frontier Logo
1:02 pm - 7:44 pm
ORD
-
OAK
8h 42m
1 stop
$250Frontier
Thu, Sep 10 - Mon, Sep 14
Frontier Logo
12:13 pm - 10:01 am
OAK
-
ORD
19h 48m
2 stops
Frontier Logo
1:02 pm - 11:18 am
ORD
-
OAK
24h 16m
1 stop
$251Frontier
Tue, Sep 8 - Mon, Sep 14
Frontier Logo
8:39 pm - 5:42 am
OAK
-
ORD
7h 03m
1 stop
Frontier Logo
1:02 pm - 7:44 pm
ORD
-
OAK
8h 42m
1 stop
$252Frontier
Fri, Sep 11 - Mon, Sep 14
Frontier Logo
8:37 pm - 7:02 pm
OAK
-
ORD
20h 25m
1 stop
Frontier Logo
8:11 pm - 11:18 am
ORD
-
OAK
17h 07m
1 stop
$254Frontier
Thu, Sep 3 - Mon, Sep 7
Frontier Logo
12:13 pm - 5:42 am
OAK
-
ORD
15h 29m
1 stop
Frontier Logo
1:02 pm - 7:44 pm
ORD
-
OAK
8h 42m
1 stop
$255Frontier
Tue, Sep 22 - Fri, Sep 25

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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
Aug 5
OAK12:33 pmOakland
7h 00m
1 stop
ORD9:33 pmChicago O'Hare Intl
Aug 14
ORD1:59 pmChicago O'Hare Intl
11h 57m
2 stops
OAK11:56 pmOakland
$473
Delta
Aug 7
OAK12:33 pmOakland
7h 00m
1 stop
ORD9:33 pmChicago O'Hare Intl
Aug 22
ORD2:30 pmChicago O'Hare Intl
10h 08m
2 stops
OAK10:38 pmOakland
$491
Delta
Aug 7
OAK12:33 pmOakland
7h 00m
1 stop
ORD9:33 pmChicago O'Hare Intl
Aug 21
ORD1:59 pmChicago O'Hare Intl
11h 57m
2 stops
OAK11:56 pmOakland
$500

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 17
OAK2:50 pmOakland
6h 46m
1 stop
ORD11:36 pmChicago O'Hare Intl
Aug 25
ORD6:01 amChicago O'Hare Intl
7h 05m
1 stop
OAK11:06 amOakland
$257
Alaska Airlines
Sep 6
OAK3:13 pmOakland
6h 46m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 16
ORD7:20 amChicago O'Hare Intl
9h 13m
1 stop
OAK2:33 pmOakland
$262
Alaska Airlines
Sep 6
OAK6:48 amOakland
10h 33m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 12
ORD2:18 pmChicago O'Hare Intl
7h 34m
1 stop
OAK7:52 pmOakland
$273

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 July 24, 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

Wed 9/9

12:13 pm-5:42 am

1 stop15h 29m

Chicago O'Hare Intl

Tue 9/15

2:46 pm-11:18 am

2 stops22h 32m

$232

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/9

12:13 pm-5:42 am

1 stop15h 29m

Chicago O'Hare Intl

Mon 9/14

2:46 pm-11:18 am

2 stops22h 32m

$236

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/10

8:39 pm-11:57 am

1 stop13h 18m

Chicago O'Hare Intl

Sat 9/12

6:50 am-11:18 am

1 stop6h 28m

$244

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/3

8:37 pm-7:02 pm

1 stop20h 25m

Chicago O'Hare Intl

Thu 9/10

6:50 am-7:44 pm

1 stop14h 54m

$246

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/9

12:13 pm-5:42 am

1 stop15h 29m

Chicago O'Hare Intl

Tue 9/15

6:50 am-11:18 am

1 stop30h 28m

$247

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/10

8:39 pm-11:57 am

1 stop13h 18m

Chicago O'Hare Intl

Mon 9/14

1:02 pm-7:44 pm

1 stop8h 42m

$250

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/8

12:13 pm-10:01 am

2 stops19h 48m

Chicago O'Hare Intl

Mon 9/14

1:02 pm-11:18 am

1 stop24h 16m

$251
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/11

8:39 pm-5:42 am

1 stop7h 03m

Chicago O'Hare Intl

Mon 9/14

1:02 pm-7:44 pm

1 stop8h 42m

$252

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/3

8:37 pm-7:02 pm

1 stop20h 25m

Chicago O'Hare Intl

Mon 9/7

8:11 pm-11:18 am

1 stop17h 07m

$254

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/22

12:13 pm-5:42 am

1 stop15h 29m

Chicago O'Hare Intl

Fri 9/25

1:02 pm-7:44 pm

1 stop8h 42m

$255

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?

Prices are currently low for flights on this route.

Typical prices usually range from $364 to $490.
The lowest price recently found on this route was $232.

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

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $367.

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 $445. 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 $575.

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 $468 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $508. 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 29% 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 38m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 38m
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 38m 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
DeltaPriceFrom $148Free CancellationRating
7.8
8,483 reviews
Search Delta flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
10,026 reviews
Search United Airlines flights
SouthwestPriceFrom $269Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $272Free CancellationRating
7.9
12,706 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
Merrillville
Rockford
Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
Joliet
New Buffalo
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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