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Cheap flights from Oakland, California to Chicago from $109

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 5/5. 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.
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$217Southwest
Wed, Mar 4 - Tue, Mar 10
Southwest Logo
6:55 pm - 4:55 am
OAK
-
MDW
8h 00m
1 stop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$227Southwest
Wed, Mar 4 - Tue, Mar 10
Alaska Airlines Logo
7:00 am - 6:46 pm
OAK
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
3:43 pm - 11:37 pm
ORD
-
OAK
9h 54m
1 stop
$237Alaska Airlines
Wed, May 13 - Tue, May 19
Southwest Logo
6:55 pm - 4:55 am
OAK
-
MDW
8h 00m
1 stop
Southwest Logo
4:00 pm - 9:35 pm
MDW
-
OAK
7h 35m
1 stop
$237Southwest
Wed, Mar 4 - Tue, Mar 10
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
3:43 pm - 11:37 pm
ORD
-
OAK
9h 54m
1 stop
$240Alaska Airlines
Tue, May 12 - Tue, May 19
Delta Logo
4:59 pm - 8:38 am
OAK
-
ORD
13h 39m
2 stops
Delta Logo
7:15 am - 11:55 am
ORD
-
OAK
6h 40m
1 stop
$242Delta
Wed, Feb 25 - Tue, Mar 3
Delta Logo
4:59 pm - 8:38 am
OAK
-
ORD
13h 39m
2 stops
Delta Logo
2:05 pm - 11:51 pm
ORD
-
OAK
11h 46m
2 stops
$248Delta
Wed, Feb 25 - Tue, Mar 3
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$250Southwest
Thu, Mar 12 - Tue, Mar 17
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
7:59 pm - 2:38 pm
ORD
-
OAK
20h 39m
1 stop
$250Alaska Airlines
Wed, Apr 29 - Mon, May 4
Southwest Logo
6:40 am - 12:45 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:55 pm - 11:50 pm
MDW
-
OAK
4h 55mnonstop
$253Southwest
Sat, Feb 21 - Sat, Feb 28

Alaska Airlines flights from Oakland, California to Chicago

Our best Alaska Airlines deals on Oakland, California to Chicago flight tickets
Alaska Airlines
May 13
OAK7:00 amOakland
9h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
May 19
ORD3:43 pmChicago O'Hare Intl
9h 54m
1 stop
OAK11:37 pmOakland
$237
Alaska Airlines
May 12
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 19
ORD3:43 pmChicago O'Hare Intl
9h 54m
1 stop
OAK11:37 pmOakland
$240
Alaska Airlines
Apr 29
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 4
ORD7:59 pmChicago O'Hare Intl
20h 39m
1 stop
OAK2:38 pmOakland
$250

Delta flights from Oakland, California to Chicago

Our best Delta deals on Oakland, California to Chicago flight tickets
Delta
Feb 25
OAK4:59 pmOakland
13h 39m
2 stops
ORD8:38 amChicago O'Hare Intl
Mar 3
ORD7:15 amChicago O'Hare Intl
6h 40m
1 stop
OAK11:55 amOakland
$242
Delta
Feb 25
OAK4:59 pmOakland
13h 39m
2 stops
ORD8:38 amChicago O'Hare Intl
Mar 3
ORD2:05 pmChicago O'Hare Intl
11h 46m
2 stops
OAK11:51 pmOakland
$248
Delta
Mar 10
OAK12:35 pmOakland
6h 59m
1 stop
ORD9:34 pmChicago O'Hare Intl
Mar 16
ORD7:10 pmChicago O'Hare Intl
6h 36m
1 stop
OAK11:46 pmOakland
$270

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California to Chicago 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 January 27, 2026.
Use the filters below to find and compare flights from Oakland, California to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 3/4

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Tue 3/10

9:00 pm-11:40 pm

Nonstop4h 40m

$217

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 3/4

6:55 pm-4:55 am

1 stop8h 00m

Chicago Midway

Tue 3/10

9:00 pm-11:40 pm

Nonstop4h 40m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/13

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 3/4

6:55 pm-4:55 am

1 stop8h 00m

Chicago Midway

Tue 3/10

4:00 pm-9:35 pm

1 stop7h 35m

$237

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/12

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$240

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/25

4:59 pm-8:38 am

2 stops13h 39m

Chicago O'Hare Intl

Tue 3/3

7:15 am-11:55 am

1 stop6h 40m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/25

4:59 pm-8:38 am

2 stops13h 39m

Chicago O'Hare Intl

Tue 3/3

2:05 pm-11:51 pm

2 stops11h 46m

$248

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 3/12

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Tue 3/17

9:00 pm-11:40 pm

Nonstop4h 40m

$250

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/29

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-2:38 pm

1 stop20h 39m

$250

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/21

6:40 am-12:45 pm

Nonstop4h 05m

Chicago Midway

Sat 2/28

8:55 pm-11:50 pm

Nonstop4h 55m

$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

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?

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Oakland, California, with most prices found around $302. If you’re not able to fly to Chicago in July, then February is your next best option. Flight prices from Oakland, California to Chicago during February average around $318.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oakland, California to Chicago for around $495.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Oakland, California to Chicago during this time can be as low as $410. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $458.

What is the cheapest Oakland to Chicago flight route?

Fly from Oakland to Chicago Midway for the best Oakland - Chicago flight prices

What cabin class options are available on Oakland to Chicago flights?

There is only 1 cabin class available to choose from on Oakland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Oakland, California to Chicago flights?

No. A direct flight is the cheapest option for a flight between Oakland, California to Chicago.

How have Oakland, California to Chicago flight prices changed over time?

As of January 2026, prices for Oakland, California to Chicago flights are approximately 80% more expensive when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago

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

Cheap Oakland, California to Chicago (OAK to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago

Best Price Found

$141

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Oakland, California in the past 72 hours is $141. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $358.
The fastest flight from Oakland, California to Chicago takes 4h 00m
Direct flights go from Oakland, California to Chicago every day.
There are 3 airports in Chicago. From Oakland, California there are direct flights to Chicago Midway (MDW).
Search flight deals

  • How far is Oakland to Chicago by plane?

    The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 00m by plane in normal conditions.

  • When did momondo last update prices for flights from Oakland Airport to Chicago?

    Prices for flights from Oakland Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Oakland Airport to Chicago?

  • How old do you have to be to fly from Oakland Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

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

  • What is the most popular plane model from Oakland, California to Chicago?

  • What is the most popular airline from Oakland, California to Chicago?

Best airlines flying from Oakland, California to Chicago

Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $108Free CancellationRating
6.3
8,384 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,207 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $189Free CancellationRating
8.0
11,799 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,268 reviews
Search Southwest flights

  • Southwest Flights From Oakland, California to Chicago

    Across 7 Southwest flights from Oakland, California to Chicago this week, the average price was $421, with the best Southwest deals starting from $246 round-trip. 4,268 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oakland.

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

momondo does allow users to show only those flights to Chicago from Oakland which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Oakland.

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

If you are not ready to book a flight from Oakland to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport