Title: Flights to Oakland from Chicago from $89 (CHI to OAK) - Expedia.com ![Downtown Oakland as seen from across Lake Merritt on a cloudy spring day, San Francisco bay area, California; Shutterstock ID 610521053; Purchase Order: -](https://images.trvl-media.com/place/553248635074843030/bfea7712-0762-48a8-aeea-516c7ac642f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074843030/bfea7712-0762-48a8-aeea-516c7ac642f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $89 Cheap Flights from Chicago (CHI) to Oakland (OAK) [View $89 flight on Tue, Apr 28, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MDW,to:OAK,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:88.40&airProductToken=AQoxCi8I15wBEgQxNzQzGOywASCOUCiOzYsDMKHPiwM4VkAAWAFqA1dHQXIHVlhOVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ## Popular airlines from Chicago to Oakland, CA (OAK-Oakland Intl.) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:OAK,departure:3/14/2026TANYT&leg2=from:OAK,to:CHI,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:OAK,departure:3/14/2026TANYT&leg2=from:OAK,to:CHI,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:OAK,departure:3/14/2026TANYT&leg2=from:OAK,to:CHI,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:OAK,departure:3/14/2026TANYT&leg2=from:OAK,to:CHI,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) ## Cheap Flights from Chicago to Oakland (CHI-OAK) Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Thu, Apr 23 - Sat, Apr 25 MDW Chicago OAK Oakland $177 Roundtrip found 22 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:4/23/2026TANYT&leg2=from:OAK,to:MDW,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:176.80&airProductToken=AQoxCi8I15wBEgQxNzQ4GOywASCOUCiqlYsDML2XiwM4VkAAWAFqA1dHQXIHVlhOVkgyTAoxCi8I15wBEgQzNTUyGI5QIOywASjfrYsDMNSviwM4VkAAWAFqA1dHQXIHVlhOVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 13 - Tue, May 19 MDW Chicago OAK Oakland $187 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:5/13/2026TANYT&leg2=from:OAK,to:MDW,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:186.60&airProductToken=AQphCi8I15wBEgQ0MjYwGOywASDLCSjq84wDMO71jAM4VkAAWAFqA1dHQXIHVlhBVkgyTAouCNecARIENDYyNhjLCSCOUCiR9owDMOH2jAM4VkABWAFqA1dHQXIHVlhBVkgyTAoxCi8I15wBEgQzNTUyGI5QIOywASjfu40DMNS9jQM4VkAAWAFqA1dHQXIHVlhOVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 14 - Wed, Apr 15 MDW Chicago OAK Oakland $192 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:4/14/2026TANYT&leg2=from:OAK,to:MDW,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:191.90&airProductToken=AQphCi8I15wBEgQzNDA0GOywASCDaSjfq4oDMPqsigM4VkAAWAFqA1dHQXIHVlhBVkgyTAouCNecARIEMTkxNBiDaSCOUCiirYoDMKuvigM4VkABWAFqA1dHQXIHVlhBVkgyTAoxCi8I15wBEgQzNTUyGI5QIOywASifvYoDMJS_igM4VkAAWAFqA1dHQXIHVlhOVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 13 - Tue, May 19 MDW Chicago OAK Oakland $197 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:5/13/2026TANYT&leg2=from:OAK,to:MDW,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.40&airProductToken=AQphCi8I15wBEgQ0MjYwGOywASDLCSjq84wDMO71jAM4VkAAWAFqA1dHQXIHVlhBVkgyTAouCNecARIENDYyNhjLCSCOUCiR9owDMOH2jAM4VkABWAFqA1dHQXIHVlhBVkgyTAphCi4I15wBEgQzNTc4GI5QIJJoKJK6jQMw7LqNAzhWQABYAWoDV0dBcgdWWEFWSDJMCi8I15wBEgQ0MDk0GJJoIOywASiUu40DMP-8jQM4VkABWAFqA1dHQXIHVlhBVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Fri, Apr 10 - Tue, Apr 14 MDW Chicago OAK Oakland $197 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:4/10/2026TANYT&leg2=from:OAK,to:MDW,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.80&airProductToken=AQoxCi8I15wBEgQxNzQ4GOywASCOUCiKg4oDMJ2FigM4VkAAWAFqA1dHQXIHVkxOVkgyRgoxCi8I15wBEgQzNTUyGI5QIOywASj_sYoDMPSzigM4VkAAWAFqA1dHQXIHVlhOVkgyTBIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 14 - Wed, Apr 15 MDW Chicago OAK Oakland $202 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:4/14/2026TANYT&leg2=from:OAK,to:MDW,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:201.70&airProductToken=AQpjCjAI15wBEgQzMzQwGOywASDvuQEo3qiKAzC_qooDOFZAAFgBagNXR0FyB1ZYQVZIMkwKLwjXnAESBDM1MjgY77kBII5QKOyqigMw9ayKAzhWQAFYAWoDV0dBcgdWWEFWSDJMCmMKLwjXnAESBDM3MTQYjlAgi5ABKIS8igMw47yKAzhWQABYAWoDV0dBcgdWWEFWSDJMCjAI15wBEgQxNDIyGIuQASDssAEo7r-KAzDAwYoDOFZAAVgBagNXR0FyB1ZYQVZIMkwSCggCEAEYAioCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Fri, Apr 24 - Tue, Apr 28 MDW Chicago OAK Oakland $207 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:OAK,departure:4/24/2026TANYT&leg2=from:OAK,to:MDW,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:206.60&airProductToken=AQoxCi8I15wBEgQxNzQ4GOywASCOUCjKoIsDMN2iiwM4VkAAWAFqA1dHQXIHVlhOVkgyTAphCi4I15wBEgQzOTU5GI5QIINpKNnIiwMw6smLAzhWQABYAWoDV0dBcgdWREFWSDJGCi8I15wBEgQxNTkwGINpIOywASibzIsDMLbNiwM4VkABWAFqA1dHQXIHVkRBVkgyRhIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Apr 21 - Sat, Apr 25 ORD Chicago OAK Oakland $220 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:4/21/2026TANYT&leg2=from:OAK,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:219.50&airProductToken=AQpECiAIwaYBEgQxNDQ3GK4cIJJoKJb8igMws_6KAzhYQABYAQogCMGmARIEMzA3NRiSaCCOUCjrhIsDMM2FiwM4WEABWAEKQgofCMGmARIDNzMzGI5QIJIBKJWpiwMwlqqLAzhYQABYAQofCMGmARIDNTM4GJIBIK4cKOqqiwMw66yLAzhYQAFYARIKCAEQARgBKgJBUxgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 14 - Wed, Apr 15 ORD Chicago OAK Oakland $247 Roundtrip found 23 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:4/14/2026TANYT&leg2=from:OAK,to:ORD,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:246.39&airProductToken=AQpECiAIxJgBEgQyMzc3GK4cIPISKOquigMwv7CKAzhFQABYAQogCMSYARIEMzc5NxjyEiCOUCiCsYoDMP6xigM4RUABWAEKRAogCMSYARIENDEzNBiOUCDyEij2t4oDMOm4igM4RUAAWAEKIAjEmAESBDI0MTMY8hIgrhwozrmKAzCKu4oDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Wed, Apr 1 - Wed, Apr 8 ORD Chicago OAK Oakland $307 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:4/1/2026TANYT&leg2=from:OAK,to:ORD,departure:4/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:306.50&airProductToken=AQpECiAIyIIBEgQ2Mjk1GK4cIJIBKKyXiQMwx5mJAzhVQABYAQogCMiCARIENjgyMBiSASCOUCjPnokDMNOfiQM4VUABWAEKRAogCMiCARIENjMyNxiOUCCSASjI5okDMMvniQM4VUAAWAEKIAjIggESBDY4MTkYkgEgrhwo0euJAzDL7YkDOFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Alternative airports near Oakland Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:RFD,to:SFO,departure:3/14/2026TANYT&leg2=from:SFO,to:RFD,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SFO San Francisco Intl. Cheapest 32 min [Flights from $302 ](https://www.expedia.com/Flights-Search?leg1=from:RFD,to:SFO,departure:3/14/2026TANYT&leg2=from:SFO,to:RFD,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SJC,departure:3/14/2026TANYT&leg2=from:SJC,to:ORD,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SJC Norman Y. Mineta San Jose Intl. 44 min [Flights from $399 ](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SJC,departure:3/14/2026TANYT&leg2=from:SJC,to:ORD,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Chicago (CHI) to Oakland (OAK) ### January is typically the cheapest month to fly From $123 - $408 per traveler. ## Travel information | Origin airport | Midway Intl. | | ------------------- | ------------------------------------------------------------- | | Destination airport | Oakland Intl. | | Airlines serving | Alaska Airlines, Delta, Hawaiian Airlines, Southwest Airlines | | Roundtrip price | $177 | | Distance | 1840 mi | ## Book with confidence # Chicago to Oakland Flights The cheapest times to fly from Chicago to Oakland On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Oakland are during the month of April. You can find some of the cheapest flights from Chicago to Oakland with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Oakland Sunday is one of the best days to book for cheap flights from Chicago to Oakland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Chicago to Oakland Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Oakland in 2026\. You can also book with separate airlines for your outbound and return journeys, from $89 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Oakland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to Oakland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. 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