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Cheap flights from Oakland, California to Chicago from $99

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 5/13. 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
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.
Alaska Airlines Logo
7:00 am - 6:46 pm
OAK
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
9:00 am - 2:32 pm
ORD
-
OAK
7h 32m
1 stop
$197Alaska Airlines
Tue, May 19 - Wed, May 20
Alaska Airlines Logo
7:19 pm - 1:13 pm
OAK
-
ORD
15h 54m
1 stop
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$223Alaska Airlines
Wed, Apr 29 - Mon, May 4
Alaska Airlines Logo
6:40 pm - 6:40 am
OAK
-
ORD
10h 00m
1 stop
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$230Alaska Airlines
Tue, Apr 21 - Mon, Apr 27
Alaska Airlines Logo
10:29 am - 6:46 pm
OAK
-
ORD
6h 17m
1 stop
Alaska Airlines Logo
9:00 am - 11:37 pm
ORD
-
OAK
16h 37m
1 stop
$233Alaska Airlines
Wed, May 13 - Sat, May 16
Delta Logo
12:40 pm - 9:52 pm
OAK
-
ORD
7h 12m
1 stop
Delta Logo
6:45 pm - 11:51 pm
ORD
-
OAK
7h 06m
1 stop
$237Delta
Sat, Feb 28 - Mon, Mar 2
Delta Logo
12:40 pm - 9:52 pm
OAK
-
ORD
7h 12m
1 stop
Delta Logo
6:15 am - 4:00 pm
ORD
-
OAK
11h 45m
2 stops
$242Delta
Tue, Mar 3 - Tue, Mar 10
Alaska Airlines Logo
3:18 pm - 11:43 pm
OAK
-
ORD
6h 25m
1 stop
Alaska Airlines Logo
3:52 pm - 6:15 pm
ORD
-
OAK
28h 23m
1 stop
$243Alaska Airlines
Mon, Apr 27 - Fri, May 1
Delta Logo
5:55 am - 6:01 pm
OAK
-
ORD
10h 06m
2 stops
Delta Logo
1:57 pm - 11:46 pm
ORD
-
OAK
11h 49m
2 stops
$247Delta
Thu, Mar 5 - Tue, Mar 10
Alaska Airlines Logo
3:18 pm - 1:13 pm
OAK
-
ORD
19h 55m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$248Alaska Airlines
Mon, Apr 27 - Thu, Apr 30
Alaska Airlines Logo
1:00 pm - 11:59 pm
OAK
-
ORD
8h 59m
1 stop
Alaska Airlines Logo
7:59 pm - 9:49 am
ORD
-
OAK
15h 50m
1 stop
$253Alaska Airlines
Sat, May 16 - Mon, May 18

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 19
OAK7:00 amOakland
9h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
Jun 3
ORD9:00 amChicago O'Hare Intl
7h 32m
1 stop
OAK2:32 pmOakland
$157
Alaska Airlines
May 19
OAK7:00 amOakland
9h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
Jun 1
ORD7:59 pmChicago O'Hare Intl
15h 50m
1 stop
OAK9:49 amOakland
$169
Alaska Airlines
May 19
OAK7:00 amOakland
9h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
Jun 5
ORD7:59 pmChicago O'Hare Intl
29h 38m
1 stop
OAK11:37 pmOakland
$177

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
Apr 9
OAK12:35 pmOakland
6h 59m
1 stop
ORD9:34 pmChicago O'Hare Intl
Apr 22
ORD7:12 pmChicago O'Hare Intl
6h 42m
1 stop
OAK11:54 pmOakland
$237
Delta
Mar 3
OAK12:40 pmOakland
7h 12m
1 stop
ORD9:52 pmChicago O'Hare Intl
Mar 10
ORD6:15 amChicago O'Hare Intl
11h 45m
2 stops
OAK4:00 pmOakland
$242
Delta
Mar 5
OAK5:55 amOakland
10h 06m
2 stops
ORD6:01 pmChicago O'Hare Intl
Mar 10
ORD1:57 pmChicago O'Hare Intl
11h 49m
2 stops
OAK11:46 pmOakland
$247

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 February 6, 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

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/19

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Wed 5/20

9:00 am-2:32 pm

1 stop7h 32m

$197

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/29

7:19 pm-1:13 pm

1 stop15h 54m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-10:17 am

1 stop16h 18m

$223

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

6:40 pm-6:40 am

1 stop10h 00m

Chicago O'Hare Intl

Mon 4/27

7:59 pm-10:17 am

1 stop16h 18m

$230

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/13

10:29 am-6:46 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 5/16

9:00 am-11:37 pm

1 stop16h 37m

$233

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 2/28

12:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 3/2

6:45 pm-11:51 pm

1 stop7h 06m

$237

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

12:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Tue 3/10

6:15 am-4:00 pm

2 stops11h 45m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 4/27

3:18 pm-11:43 pm

1 stop6h 25m

Chicago O'Hare Intl

Fri 5/1

3:52 pm-6:15 pm

1 stop28h 23m

$243

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 3/5

5:55 am-6:01 pm

2 stops10h 06m

Chicago O'Hare Intl

Tue 3/10

1:57 pm-11:46 pm

2 stops11h 49m

$247

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 4/27

3:18 pm-1:13 pm

1 stop19h 55m

Chicago O'Hare Intl

Thu 4/30

3:52 pm-10:23 pm

1 stop8h 31m

$248

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/16

1:00 pm-11:59 pm

1 stop8h 59m

Chicago O'Hare Intl

Mon 5/18

7:59 pm-9:49 am

1 stop15h 50m

$253

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of July is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $259.

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 $407. 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 $494.

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 $410 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $456. 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 22% 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?

As of February 2026, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 147% more expensive when compared to flights at the same time last year.

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 05m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 05m
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

  • 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 05m 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
8,420 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,242 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $189Free CancellationRating
8.0
11,843 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,278 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
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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