Deal Alert: NYC and Chicago to Oakland From $138 Round-Trip
Update: Some offers mentioned below are no longer available. View the current offers here.
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Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. However, if you’re using the American Express Platinum Card, you’ll need to book directly with the airline or through Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family.
Alaska Airlines is offering cheap transcontinental fares from New York (EWR) to Oakland (OAK). With these fares, you can book a round-trip ticket for just $138. We're also seeing the same round-trip fares between OAK and Chicago (ORD). In addition, all of these are vice versa — meaning you can fly from the Bay Area to NYC or Chicago for just $138 round-trip. Service each way and from both cities will require a stop in Seattle (SEA).
Availability is fairly limited, showing up just between September and October 2018. To search, you'll want to use Google Flights' calendar function and then click through to book directly with Alaska.
Routes: EWR/ORD to/from OAK
Cost: $138+ round-trip in economy
Dates: September-October 2018
Booking Link: Orbitz, Expedia or directly with the airline
Pay With: The Platinum Card from American Express (5x on airfare), Chase Sapphire Reserve, Citi Prestige (5x on airfare plus excellent trip delay insurance) or Chase Sapphire Preferred Card (2x on travel)
Here are some examples of what you can book:
New York (EWR) to Oakland (OAK) for $138 round-trip in September:
New York (EWR) to Oakland (OAK) for $138 round-trip in October:
Oakland (OAK) to New York (EWR) for $138 round-trip in October:
Chicago (ORD) to Oakland (OAK) for $138 round-trip in October:
Maximize Your Purchase
Don’t forget to use a credit card that earns additional points on airfare purchases, such as the American Express Platinum Card (5x on flights booked directly with airlines or American Express Travel), Chase Sapphire Reserve, or Citi Prestige (5x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.
H/T: The Flight Deal