Title: CA $198 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 $198 Cheap Flights from Chicago (CHI) to Oakland (OAK) [View CA $198 flight on Thu, Jan 22, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.30&airProductToken=AQpfCi0IwaYBEgM1ODcYrhwgkgEoyI-DAzDmkYMDOFhAAFgBagJTVnIIR0gyT0FWQk4KLgjBpgESBDEzMjgYkgEgjlAotpODAzC3lIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Chicago to Oakland, CA (OAK-Oakland Intl.) - ![Alaska Airlines](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:13/11/2025TANYT&leg2=from:oak,to:chi,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Southwest Airlines](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:13/11/2025TANYT&leg2=from:oak,to:chi,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Delta](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:13/11/2025TANYT&leg2=from:oak,to:chi,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:oak,departure:13/11/2025TANYT&leg2=from:oak,to:chi,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](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 $198 for one-way flights and CA $395 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $395 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:394.70&airProductToken=AQpfCi0IwaYBEgM1ODcYrhwgkgEoyI-DAzDmkYMDOFhAAFgBagJTVnIIR0gyT0FWQk4KLgjBpgESBDEzMjgYkgEgjlAotpODAzC3lIMDOFhAAVgBagJTVnIIR0gyT0FWQk4KXgotCMGmARIDNzA1GI5QIJIBKKqygwMwrrODAzhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgM1MzgYkgEgrhwo7raDAzDjuIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $416 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:415.90&airProductToken=AQpfCi0IwaYBEgM1ODcYrhwgkgEoyI-DAzDmkYMDOFhAAFgBagJTVnIIR0gyT0FWQk4KLgjBpgESBDEzMjgYkgEgjlAotpODAzC3lIMDOFhAAVgBagJTVnIIR0gyT0FWQk4KkAEKLwjBpgESBDIwOTQYjlAg77gBKLazgwMwn7SDAzhYQABYAWoCU1ZyCEdIMk9BSkJOCi4IwaYBEgMzNzEY77gBIJIBKPK0gwMws7WDAzhYQAFYAWoCU1ZyCEdIMk9BSkJOCi0IwaYBEgM1MzgYkgEgrhwo7raDAzDjuIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $419 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:418.30&airProductToken=AQphCi4IwaYBEgMzMjUYrhwg77gBKLaSgwMw0JSDAzhYQABYAWoCU1ZyCE9IMk9RSkJOCi8IwaYBEgQyMjgzGO-4ASCOUCj8lIMDMOuVgwM4WEABWAFqAlNWcghPSDJPUUpCTgpeCi0IwaYBEgM3MDUYjlAgkgEoqrKDAzCus4MDOFhAAFgBagJTVnIIR0gyT0FWQk4KLQjBpgESAzUzOBiSASCuHCjutoMDMOO4gwM4WEABWAFqAlNWcghHSDJPQVZCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $423 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:422.60&airProductToken=AQpeCi0IwaYBEgM1ODcYrhwgkgEoyI-DAzDmkYMDOFhAAFgBagJTVnIIR0gyT0FWQk4KLQjBpgESAzcwNhiSASCOUCi4lYMDMLiWgwM4WEABWAFqAlNWcghHSDJPQVZCTgpfCi4IwaYBEgQzMDI2GI5QIJIBKNyzgwMw47SDAzhYQABYAWoCU1ZyCE9IMk9BVUJOCi0IwaYBEgM1MzgYkgEgrhwo7raDAzDjuIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $440 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:439.60&airProductToken=AQphCi4IwaYBEgMzMjUYrhwg77gBKLaSgwMw0JSDAzhYQABYAWoCU1ZyCE9IMk9RSkJOCi8IwaYBEgQyMjgzGO-4ASCOUCj8lIMDMOuVgwM4WEABWAFqAlNWcghPSDJPUUpCTgqQAQovCMGmARIEMjA5NBiOUCDvuAEotrODAzCftIMDOFhAAFgBagJTVnIIR0gyT0FKQk4KLgjBpgESAzM3MRjvuAEgkgEo8rSDAzCztYMDOFhAAVgBagJTVnIIR0gyT0FKQk4KLQjBpgESAzUzOBiSASCuHCjutoMDMOO4gwM4WEABWAFqAlNWcghHSDJPQVZCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $447 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:446.30&airProductToken=AQphCi4IwaYBEgMzMjUYrhwg77gBKLaSgwMw0JSDAzhYQABYAWoCU1ZyCE9IMk9RSkJOCi8IwaYBEgQyMjgzGO-4ASCOUCj8lIMDMOuVgwM4WEABWAFqAlNWcghPSDJPUUpCTgpfCi4IwaYBEgQzMDI2GI5QIJIBKNyzgwMw47SDAzhYQABYAWoCU1ZyCE9IMk9BVUJOCi0IwaYBEgM1MzgYkgEgrhwo7raDAzDjuIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $494 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:493.33&airProductToken=AQpuCjUIxJgBEgQyMjMxGK4cIPISKKCPgwMwi5GDAzhFQABYAWoJTUFJTkJBU0lDcghVQVZOQTBCQwo1CMSYARIENDEzNBjyEiCOUCiukYMDMK2SgwM4RUABWAFqCU1BSU5CQVNJQ3IIVUFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $507 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:506.96&airProductToken=AQpuCjUIxJgBEgQyMjMxGK4cIPISKKCPgwMwi5GDAzhFQABYAWoJTUFJTkJBU0lDcghVQVZOQTBCQwo1CMSYARIENDEzNBjyEiCOUCiukYMDMK2SgwM4RUABWAFqCU1BSU5CQVNJQ3IIVUFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $522 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:521.59&airProductToken=AQpuCjUIxJgBEgQyMjMxGK4cIPISKKCPgwMwi5GDAzhFQABYAWoJTUFJTkJBU0lDcghVQVZOQTBCQwo1CMSYARIENDEzNBjyEiCOUCiukYMDMK2SgwM4RUABWAFqCU1BSU5CQVNJQ3IIVUFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Jan 22 - Sun, Jan 25 ORD Chicago OAK Oakland CA $582 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:OAK,departure:22/01/2026TANYT&leg2=from:OAK,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:581.10&airProductToken=AQpfCi0IwaYBEgM1ODcYrhwgkgEoyI-DAzDmkYMDOFhAAFgBagJTVnIIR0gyT0FWQk4KLgjBpgESBDEzMjgYkgEgjlAotpODAzC3lIMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Chicago (CHI) to Oakland (OAK) ### January is typically the cheapest month to fly From CA $158 - CA $541 per traveller. ## 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:13/11/2025TANYT&leg2=from:SFO,to:ORD,departure:17/11/2025TANYT&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 CA $494](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:SFO,departure:13/11/2025TANYT&leg2=from:SFO,to:ORD,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Chicago to Oakland (ORD - OAK) route information | Origin airport | O'Hare Intl. | | --- | --- | | Destination airport | Oakland Intl. | | Roundtrip price | CA $395 | | Distance | 2929 km | ## 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 $395 rising to CA $582.   Here are more money-saving tips:  - Fly in January 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. ## Explore a world of travel with Expedia \*Available to Expedia members.