Title: CA $217 Cheap Flights from Chicago (CHI) to Oakland (OAK) - Expedia.ca ![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) # CA $217 Cheap Flights from Chicago (CHI) to Oakland (OAK) [View CA $217 flight on Thu, Jun 4, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:OAK,departure:04/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.70&airProductToken=AQqmAQo2CMSYARIEMTcxNhiuHCDjtAEolOqOAzDq6o4DOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBNUJDCjUIxJgBEgM3NjUY47QBIPISKLfrjgMwoO2OAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTVCQwo1CMSYARIEMzc5NxjyEiCOUCjr7o4DMOHvjgM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## 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.ca/Flights-Search?leg1=from:CHI,to:OAK,departure:28/03/2026TANYT&leg2=from:OAK,to:CHI,departure:04/04/2026TANYT&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.ca/Flights-Search?leg1=from:CHI,to:OAK,departure:28/03/2026TANYT&leg2=from:OAK,to:CHI,departure:04/04/2026TANYT&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.ca/Flights-Search?leg1=from:CHI,to:OAK,departure:28/03/2026TANYT&leg2=from:OAK,to:CHI,departure:04/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Chicago (CHI) to Oakland (OAK) Prices were available within the past 7 days and start at CA $217 for one-way flights and CA $388 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Mar 31 - Wed, Apr 1 ORD Chicago OAK Oakland CA $388 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:31/03/2026TANYT&leg2=from:OAK,to:ORD,departure:01/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:387.90&airProductToken=AQpECiAIxJgBEgQyMjMxGK4cIPISKOSLiQMwyI2JAzhFQABYAQogCMSYARIENDEzNBjyEiCOUCjyjYkDMOuOiQM4RUABWAEKRAogCMSYARIENDEzNBiOUCDyEii3mokDMKmbiQM4RUAAWAEKIAjEmAESBDI0MTMY8hIgrhwoopyJAzDanYkDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Mar 30 - Wed, Apr 1 ORD Chicago OAK Oakland CA $473 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:30/03/2026TANYT&leg2=from:OAK,to:ORD,departure:01/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:472.80&airProductToken=AQpECiAIxJgBEgQyMzc3GK4cIPISKIqGiQMw44eJAzhFQABYAQogCMSYARIEMzc5NxjyEiCOUCiiiIkDMJaJiQM4RUABWAEKRAogCMSYARIENDEzNBiOUCDyEii3mokDMKmbiQM4RUAAWAEKIAjEmAESBDI0MTMY8hIgrhwoopyJAzDanYkDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Tue, Mar 31 - Tue, Apr 7 ORD Chicago OAK Oakland CA $509 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:31/03/2026TANYT&leg2=from:OAK,to:ORD,departure:07/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:508.30&airProductToken=AQpECiAIyIIBEgQ2Mjk5GK4cIJIBKJSLiQMwqY2JAzhVQABYAQogCMiCARIENjgyMBiSASCOUCivk4kDMLOUiQM4VUABWAEKRAogCMiCARIENDk5NBiOUCCSASjk4IkDMOThiQM4VUAAWAEKIAjIggESBDY4MTkYkgEgrhwo0euJAzDL7YkDOFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Mar 28 - Wed, Apr 1 ORD Chicago OAK Oakland CA $533 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:28/03/2026TANYT&leg2=from:OAK,to:ORD,departure:01/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:533.00&airProductToken=AQpECiAIxJgBEgQyMjQ3GK4cIPISKMjuiAMwqPCIAzhFQABYAQogCMSYARIEMzc5NxjyEiCOUCjq8IgDMNvxiAM4RUABWAEKRAogCMSYARIENDEzNBiOUCDyEii3mokDMKmbiQM4RUAAWAEKIAjEmAESBDI0MTMY8hIgrhwoopyJAzDanYkDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Wed, Apr 1 - Tue, Apr 7 ORD Chicago OAK Oakland CA $537 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:01/04/2026TANYT&leg2=from:OAK,to:ORD,departure:07/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:536.20&airProductToken=AQpECiAIyIIBEgQ2Mjk1GK4cIJIBKKyXiQMwx5mJAzhVQABYAQogCMiCARIENjgyMBiSASCOUCjPnokDMNOfiQM4VUABWAEKRAogCMiCARIENDk5NBiOUCCSASjk4IkDMOThiQM4VUAAWAEKIAjIggESBDY4MTkYkgEgrhwo0euJAzDL7YkDOFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Apr 2 - Tue, Apr 7 ORD Chicago OAK Oakland CA $555 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:02/04/2026TANYT&leg2=from:OAK,to:ORD,departure:07/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:554.50&airProductToken=AQpECiAIxJgBEgQyMzc3GK4cIPISKOqniQMww6mJAzhFQABYAQogCMSYARIEMzc5NxjyEiCOUCiCqokDMPaqiQM4RUABWAEKRAogCMSYARIENDEzNBiOUCDyEij33YkDMOneiQM4RUAAWAEKIAjEmAESBDI0MTMY8hIgrhwo4t-JAzCa4YkDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jun 4 - Wed, Jul 1 ORD Chicago OAK Oakland CA $579 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:04/06/2026TANYT&leg2=from:OAK,to:ORD,departure:01/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:578.20&airProductToken=AQpgCi4IwaYBEgQxNDcwGK4cIJJoKOjnjgMw_emOAzhYQABYAWoCU1ZyCFFIMk9aVkJOCi4IwaYBEgQzMDc3GJJoII5QKLHsjgMwke2OAzhYQAFYAWoCU1ZyCFFIMk9aVkJOCl4KLQjBpgESAzQ5MRiOUCCSASigl5EDMJ6YkQM4WEAAWAFqAlNWcghRSDJPR0pCTgotCMGmARIDNDI5GJIBIK4cKJWZkQMwl5uRAzhYQAFYAWoCU1ZyCFFIMk9HSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Mar 31 - Mon, Apr 6 ORD Chicago OAK Oakland CA $583 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:31/03/2026TANYT&leg2=from:OAK,to:ORD,departure:06/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:582.50&airProductToken=AQpCCh8IwaYBEgMzNDkYrhwgkgEolIuJAzCpjYkDOFhAAFgBCh8IwaYBEgM3MDYYkgEgjlAor5OJAzCzlIkDOFhAAVgBCkUKIQjBpgESBDIwNjYYjlAg77gBKJ7WiQMwhdeJAzhYQABYAQogCMGmARIDMzI0GO-4ASCuHCir24kDMKXdiQM4WEABWAESCggBEAEYASoCQVMYASIECAEQASgEMAE) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Wed, Apr 1 - Mon, Apr 6 ORD Chicago OAK Oakland CA $610 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:01/04/2026TANYT&leg2=from:OAK,to:ORD,departure:06/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:609.30&airProductToken=AQpECiAIyIIBEgQ2Mjk1GK4cIJIBKKyXiQMwx5mJAzhVQABYAQogCMiCARIENjgyMBiSASCOUCjPnokDMNOfiQM4VUABWAEKRgohCMiCARIENDk5MRiOUCDvuAEontaJAzCF14kDOFVAAFgBCiEIyIIBEgQ2MzczGO-4ASCuHCir24kDMKXdiQM4VUABWAESCggBEAEYASoCSEEYASIECAEQASgEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jun 4 - Wed, Jul 1 ORD Chicago OAK Oakland CA $618 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:04/06/2026TANYT&leg2=from:OAK,to:ORD,departure:01/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:617.90&airProductToken=AQpgCi4IwaYBEgQxNDcwGK4cIJJoKOjnjgMw_emOAzhYQABYAWoCU1ZyCE5IMk9BU0JOCi4IwaYBEgQzMDc2GJJoII5QKLfqjgMwmuuOAzhYQAFYAWoCU1ZyCE5IMk9BU0JOCl4KLQjBpgESAzQ5MRiOUCCSASigl5EDMJ6YkQM4WEAAWAFqAlNWcghRSDJPR0pCTgotCMGmARIDNDI5GJIBIK4cKJWZkQMwl5uRAzhYQAFYAWoCU1ZyCFFIMk9HSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![](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.ca/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.ca/Flights-Search?leg1=from:ORD,to:SFO,departure:28/03/2026TANYT&leg2=from:SFO,to:ORD,departure:30/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SFO San Francisco Intl. 32 min [Flights from CA $648 ](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:SFO,departure:28/03/2026TANYT&leg2=from:SFO,to:ORD,departure:30/03/2026TANYT&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 CA $173 - CA $576 per traveller. ## Travel information | Origin airport | O'Hare Intl. | | ------------------- | ------------- | | Destination airport | Oakland Intl. | | Roundtrip price | CA $388 | | Distance | 2929 km | ## Book with confidence # Illinois to Oakland Flights **The easy way to book your flights from Chicago to Oakland** With Expedia, it’s simple to find and book flights to Oakland from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Oakland Intl., too. Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Oakland today, tomorrow, or this week. **Save dollars with cheap flights from CHI-All Airports, CHI to Oakland Intl., OAK** Sort your search results by price to find great deals on your flight from Chicago to Oakland—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Oakland from Chicago currently is just CA $388 rising to CA $618\. Here are more money-saving tips: - Fly in March when flight prices are normally at their lowest - Book about a month to 6 weeks before you travel for the best prices to Oakland - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! **Reasons to choose Expedia for your flight to Oakland from Chicago** Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Oakland with Expedia today. \*Available to Expedia members.