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Cheap flights from Oakland, California to Chicago from $89

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 9/21. 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
6:51 pm - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
8h 47m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 5:56 pmORD  Chicago O'Hare Intl-OAK Oakland
23h 01m1 stop Las Vegas Harry Reid Intl
$178Frontier
Thu, Sep 17 - Thu, Sep 24
Frontier Logo
8:39 pm - 11:57 amOAK  Oakland-ORD Chicago O'Hare Intl
13h 18m1 stop Las Vegas Harry Reid Intl
Frontier Logo
6:50 am - 11:18 amORD  Chicago O'Hare Intl-OAK Oakland
6h 28m1 stop Las Vegas Harry Reid Intl
$178Frontier
Thu, Oct 15 - Tue, Oct 20
Frontier Logo
6:51 pm - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
8h 47m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
$178Frontier
Thu, Sep 17 - Mon, Sep 21
Frontier Logo
6:51 pm - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
8h 47m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 9:22 amORD  Chicago O'Hare Intl-OAK Oakland
14h 27m1 stop Las Vegas Harry Reid Intl
$178Frontier
Mon, Sep 21 - Thu, Sep 24
Delta Logo
5:00 pm - 9:40 amOAK  Oakland-ORD Chicago O'Hare Intl
14h 40m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
5:10 pm - 11:59 pmORD  Chicago O'Hare Intl-OAK Oakland
8h 49m2 stops Detroit Metropolitan Wayne County Salt Lake City
$267Delta
Sat, Sep 5 - Fri, Sep 11
Alaska Airlines Logo
3:13 pm - 1:22 pmOAK  Oakland-ORD Chicago O'Hare Intl
20h 09m1 stop San Diego
Alaska Airlines Logo
8:17 pm - 11:06 amORD  Chicago O'Hare Intl-OAK Oakland
16h 49m1 stop San Diego
$277Alaska Airlines
Wed, Aug 26 - Mon, Aug 31
Alaska Airlines Logo
3:13 pm - 11:59 pmOAK  Oakland-ORD Chicago O'Hare Intl
6h 46m1 stop San Diego
Alaska Airlines Logo
7:20 am - 2:33 pmORD  Chicago O'Hare Intl-OAK Oakland
9h 13m1 stop San Diego
$277Alaska Airlines
Thu, Sep 10 - Thu, Sep 17
Alaska Airlines Logo
3:13 pm - 11:59 pmOAK  Oakland-ORD Chicago O'Hare Intl
6h 46m1 stop San Diego
Alaska Airlines Logo
2:18 pm - 7:52 pmORD  Chicago O'Hare Intl-OAK Oakland
7h 34m1 stop San Diego
$277Alaska Airlines
Thu, Sep 17 - Sat, Sep 19
Delta Logo
6:00 am - 4:17 pmOAK  Oakland-ORD Chicago O'Hare Intl
8h 17m2 stops Salt Lake City Detroit Metropolitan Wayne County
Delta Logo
4:45 pm - 10:38 pmORD  Chicago O'Hare Intl-OAK Oakland
7h 53m1 stop Salt Lake City
$316Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
6:00 am - 4:17 pmOAK  Oakland-ORD Chicago O'Hare Intl
8h 17m2 stops Salt Lake City Detroit Metropolitan Wayne County
Delta Logo
8:28 am - 4:14 pmORD  Chicago O'Hare Intl-OAK Oakland
9h 46m2 stops Minneapolis St Paul Salt Lake City
$321Delta
Wed, Sep 2 - Sat, Sep 5

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

Our best Frontier deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Frontier
Sep 17
OAK6:51 pmOakland
8h 47m
1 stop
ORD5:38 amChicago O'Hare Intl
Sep 21
ORD8:55 pmChicago O'Hare Intl
16h 56m
1 stop
OAK11:51 amOakland
$178
Frontier
Sep 14
OAK10:17 amOakland
17h 21m
1 stop
ORD5:38 amChicago O'Hare Intl
Sep 15
ORD1:21 pmChicago O'Hare Intl
24h 30m
1 stop
OAK11:51 amOakland
$188
Frontier
Sep 9
OAK12:47 pmOakland
14h 51m
1 stop
ORD5:38 amChicago O'Hare Intl
Sep 11
ORD8:55 pmChicago O'Hare Intl
16h 56m
1 stop
OAK11:51 amOakland
$208

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
Sep 10
OAK6:48 amOakland
10h 33m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 14
ORD8:17 pmChicago O'Hare Intl
16h 49m
1 stop
OAK11:06 amOakland
$277
Alaska Airlines
Sep 5
OAK5:10 pmOakland
18h 12m
1 stop
ORD1:22 pmChicago O'Hare Intl
Sep 11
ORD2:18 pmChicago O'Hare Intl
10h 52m
1 stop
OAK11:10 pmOakland
$283
Alaska Airlines
Sep 11
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
$284

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 August 10, 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 Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/17

6:51 pm-5:38 am

1 stop8h 47m

Chicago O'Hare Intl

Thu 9/24

8:55 pm-5:56 pm

1 stop23h 01m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 10/15

8:39 pm-11:57 am

1 stop13h 18m

Chicago O'Hare Intl

Tue 10/20

6:50 am-11:18 am

1 stop6h 28m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/17

6:51 pm-5:38 am

1 stop8h 47m

Chicago O'Hare Intl

Mon 9/21

8:55 pm-11:51 am

1 stop16h 56m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Mon 9/21

6:51 pm-5:38 am

1 stop8h 47m

Chicago O'Hare Intl

Thu 9/24

8:55 pm-9:22 am

1 stop14h 27m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Sat 9/5

5:00 pm-9:40 am

2 stops14h 40m

Chicago O'Hare Intl

Fri 9/11

5:10 pm-11:59 pm

2 stops8h 49m

$267

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 8/26

3:13 pm-1:22 pm

1 stop20h 09m

Chicago O'Hare Intl

Mon 8/31

8:17 pm-11:06 am

1 stop16h 49m

$277

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/10

3:13 pm-11:59 pm

1 stop6h 46m

Chicago O'Hare Intl

Thu 9/17

7:20 am-2:33 pm

1 stop9h 13m

$277
Quickest round-trip

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/17

3:13 pm-11:59 pm

1 stop6h 46m

Chicago O'Hare Intl

Sat 9/19

2:18 pm-7:52 pm

1 stop7h 34m

$277

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 9/2

6:00 am-4:17 pm

2 stops8h 17m

Chicago O'Hare Intl

Sat 9/5

4:45 pm-10:38 pm

1 stop7h 53m

$316

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 9/2

6:00 am-4:17 pm

2 stops8h 17m

Chicago O'Hare Intl

Sat 9/5

8:28 am-4:14 pm

2 stops9h 46m

$321

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 $384 to $542.
The lowest price recently found on this route was $178.

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 $444. 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 $578.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $470 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $509. 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 37% 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
8,497 reviews
Search Delta flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
10,099 reviews
Search United Airlines flights
SouthwestPriceFrom $269Free CancellationRating
8.0
4,218 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $272Free CancellationRating
7.9
12,794 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
Merrillville
Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
South Holland
Evanston

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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