If you want a chance to travel to Chicago or Oakland, here’s a great opportunity for you! If so, you can get a Round-Trip flight with Alaska Airlines from Chicago, IL to Oakland, CA (vice versa) starting at $141. Chicago, known as the “Windy City,” is among the largest cities in the United States, famed for the beautiful architecture and mighty skyscrapers such as the iconic Willis Tower! If you’re heading to Oakland, CA, then be sure to take an adventurous hike at Angel Island, Tilden Regional Park, or shop at the Jack London Square. There’s so many things to do in both cities, so if you’re planning to head to either cities, be sure to take advantage of this flight deal!
We recommend you look up your preferred dates on Google Flights in case there is a cheaper price than the ones we listed. Depending when you book, the prices can change! (YMMV) The airline fares rule associated with your flight and be reviewed over pre-purchase, on your contract, and post purchase with the itinerary displayed on their website, be sure you read their full terms before making your purchase.
Flights from Chicago to Oakland
- Buy It Now
- Promotion: Round-trip starting at $141
- Routes: From Chicago, IL to Oakland, CA
- Distance: 2,125.6 miles
| Departure | Destination |
|---|---|
| Chicago (ORD) | Oakland (OAK) |
We used the dates of September 9th through September 29th, 2018, to trigger this offer but you can always try your own dates and cities in case you can catch the same or better deal!
- Valid: Valid for travel from late September – October 2018. Availability is limited. Must purchase at least 21 days in advance of departure.
- Terms: Prices shown based on searches made in the last 24 hours. Due to constant changing availability, these fares may no longer be available. For FAQ you can contact your airlines at their Help page. Baggage fees are not included in your trip cost unless otherwise stated and will be charged directly by the airline at check-in. Please visit your chosen carrier to review all fare cost including taxes and baggage fees. Purchases must be made at least 2 weeks in advance of departure.
How To Get SFO/ORD Flight Deal:
- Use Priceline to check the flights and times that fit best for you. We recommend selecting United Airlines since their prices seem to be the cheapest. (YMMV)
- To earn cash back we highly recommend using AMEX Premier Rewards Gold Card to save the most money.
- Once you found the times that you would like to make sure you book it early so that it doesn’t change.
Bottom Line:
This is a great trip to take a vacation! Plan early in order to receive this benefit. I highly recommend going so you can experience a new part of the world! Make sure you use your Citi Hilton HHonors Visa Signature Card to save the maximum amount of money! This card is great for traveling anywhere. US citizens should visit the US Passports & International Travel website for the latest information, including exercising safety abroad and entry requirements. This is the cheapest fare I found but please let us know if you got anything different!
 The Southwest Rapid Rewards® Premier Credit Card offers Companion Pass through 2/28/26 and 30,000 bonus points after spending $4,000 on purchases in the first 3 months from account opening. In addition, you'll earn 6,000 bonus points after your Cardmember anniversary each year. You'll earn: • Earn 3X points on Southwest purchases. • Earn 2X points on local transit and commuting, including rideshare. • Earn 2X points on internet, cable, phone services, and select streaming. You're able to redeem your points for flights, hotel stays, gift cards, access to events and more. This card does carry a $99 annual fee, but there are no foreign transaction fee. |