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Flights from Chicago to Oakland
Cheap flight deals from Chicago to Oakland
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstopMDW 4:55 PM4h 35mNonstopOAK 7:30 PMChicago - Oakland | Sat, May 3 | Southwest AirlinesOAK 5:55 AM4h 10mNonstopMDW 12:05 PMOakland - Chicago | Sun, May 11 | Southwest AirlinesPHP 11,595 PHP 12,90210% OFF10% OFFPHP 12,902 PHP 11,595
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MDW 8:50 PM14h 12m1 stopsOAK 9:02 AMChicago - Oakland | Wed, Apr 9 | Frontier AirlinesOAK 7:46 AM19h 37m1 stopsMDW 5:23 AMOakland - Chicago | Mon, Apr 14 | Spirit AirlinesPHP 9,134 PHP 12,90228% OFF28% OFFPHP 12,902 PHP 9,134
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ORD 3:44 PM10h1 stopsOAK 11:44 PMChicago - Oakland | Wed, Apr 23 | Hawaiian AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Wed, Apr 30 | Hawaiian AirlinesPHP 10,647 PHP 12,90217% OFF17% OFFPHP 12,902 PHP 10,647
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ORD 3:44 PM7h 32m1 stopsOAK 9:16 PMChicago - Oakland | Tue, Apr 22 | Hawaiian AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Tue, Apr 29 | Hawaiian AirlinesPHP 10,65517% OFFPHP 12,902 PHP 10,655
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ORD 3:44 PM10h1 stopsOAK 11:44 PMChicago - Oakland | Wed, Apr 23 | Alaska AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Wed, Apr 30 | Alaska AirlinesPHP 10,90615% OFFPHP 12,902 PHP 10,906
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ORD 5:53 PM7h 50m1 stopsOAK 11:43 PMChicago - Oakland | Tue, Apr 8 | Hawaiian AirlinesOAK 6:43 AM8h 10m1 stopsORD 4:53 PMOakland - Chicago | Tue, Apr 15 | Hawaiian AirlinesPHP 11,07814% OFFPHP 12,902 PHP 11,078
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MDW 4:55 PM4h 35mNonstopOAK 7:30 PMChicago - Oakland | Wed, Apr 23 | Southwest AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Wed, Apr 30 | Alaska AirlinesPHP 11,40712% OFFPHP 12,902 PHP 11,407
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ORD 5:56 PM7h 48m1 stopsOAK 11:44 PMChicago - Oakland | Tue, Apr 22 | Alaska AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Tue, Apr 29 | Alaska AirlinesPHP 11,7219% OFFPHP 12,902 PHP 11,721
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ORD 5:53 PM7h 50m1 stopsOAK 11:43 PMChicago - Oakland | Tue, Apr 8 | Alaska AirlinesOAK 6:43 AM9h 12m1 stopsORD 5:55 PMOakland - Chicago | Tue, Apr 15 | Alaska AirlinesPHP 11,7379% OFFPHP 12,902 PHP 11,737
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ORD 5:56 PM7h 48m1 stopsOAK 11:44 PMChicago - Oakland | Thu, Apr 24 | Alaska AirlinesOAK 7:00 AM9h 1m1 stopsORD 6:01 PMOakland - Chicago | Tue, Apr 29 | Alaska AirlinesPHP 11,8708% OFFPHP 12,902 PHP 11,870
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CHI 1:00 PM17h 25m1 stopsOAK Invalid DateChicago - Oakland | Sun, Apr 6 | Normal AirlineOAK 3:00 PM6hNonstopCHI 4:00 PMOakland - Chicago | Tue, Apr 8 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopMDW 9:10 PM4h 35mNonstopOAK 11:45 PMChicago - Oakland | Thu, May 1 | Southwest AirlinesPHP 6,005 PHP 6,85212% OFF12% OFFPHP 6,852 PHP 6,005
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MDW 9:10 PM4h 35mNonstopOAK 11:45 PMChicago - Oakland | Fri, May 16 | Southwest AirlinesPHP 6,303 PHP 6,8528% OFF8% OFFPHP 6,852 PHP 6,303
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MDW 6:15 AM28h 47m1 stopsOAK 9:02 AMChicago - Oakland | Mon, Apr 28 | Frontier AirlinesPHP 4,916 PHP 6,85228% OFF28% OFFPHP 6,852 PHP 4,916
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ORD 8:01 PM15h 1m1 stopsOAK 9:02 AMChicago - Oakland | Mon, Apr 21 | Frontier AirlinesPHP 5,15125% OFFPHP 6,852 PHP 5,151
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MDW 6:15 AM15h 17m1 stopsOAK 7:32 PMChicago - Oakland | Fri, May 2 | Frontier AirlinesPHP 5,27623% OFFPHP 6,852 PHP 5,276
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MDW 6:15 AM26h 34m1 stopsOAK 6:49 AMChicago - Oakland | Sun, Apr 27 | Frontier AirlinesPHP 5,30023% OFFPHP 6,852 PHP 5,300
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ORD 3:08 PM19h 54m1 stopsOAK 9:02 AMChicago - Oakland | Mon, Apr 28 | Spirit AirlinesPHP 5,38621% OFFPHP 6,852 PHP 5,386
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ORD 7:12 PM13h 37m1 stopsOAK 6:49 AMChicago - Oakland | Sun, Apr 27 | Spirit AirlinesPHP 5,45720% OFFPHP 6,852 PHP 5,457
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ORD 9:00 AM8h 48m1 stopsOAK 3:48 PMChicago - Oakland | Wed, Apr 30 | Hawaiian AirlinesPHP 5,56619% OFFPHP 6,852 PHP 5,566
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ORD 2:58 PM17h 51m1 stopsOAK 6:49 AMChicago - Oakland | Fri, Apr 18 | Spirit AirlinesPHP 5,59818% OFFPHP 6,852 PHP 5,598
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ORD 9:00 AM8h 48m1 stopsOAK 3:48 PMChicago - Oakland | Tue, Apr 29 | Alaska AirlinesPHP 5,65317% OFFPHP 6,852 PHP 5,653
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ORD 3:44 PM7h 32m1 stopsOAK 9:16 PMChicago - Oakland | Wed, May 7 | Alaska AirlinesPHP 5,65317% OFFPHP 6,852 PHP 5,653
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CHI 1:00 PM17h 25m1 stopsOAK Invalid DateChicago - Oakland | Sun, Apr 6 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Chicago (CHI) to Oakland (OAK) the cheapest?
Airlines adjust prices for flights from Chicago to Oakland based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Chicago (CHI) to Oakland (OAK) cost?
According to Trip.com's data, the lowest price is around PHP 25,174. -
How long does it take to fly from Chicago (CHI) to Oakland (OAK) and what is the distance?
It takes around 5 hours 59 minutes to fly from Chicago (CHI) to Oakland (OAK). -
What is the transportation method from the main airport to downtown in Oakland?
- The distance from Oakland International Airport to downtown is about 11 km. It takes about 30 minutes by taxi.
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What are the most popular airlines that fly from Chicago (CHI) to Oakland (OAK)?
Airlines with flights from Chicago (CHI) to Oakland (OAK): Southwest Airlines.
How to find a cheap flight from Chicago to Oakland
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Oakland. Book your flights at the right time and save more.
Book Early
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Look Out for Deals
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Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
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Flight Info | Chicago to Oakland
Cheapest one-way flight price | PHP 4,915 |
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Cheapest round-trip ticket price | PHP 11,407 |
Off-season for travel | April |
Peak season for travel | June |
Flight distance | 2,969.56 km |
Average flight time | 5 hours 59 minutes |
Popular airline | Alaska Airlines |
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