Deal Alert: Boston and Chicago to West Coast From $98 Round-Trip

Jul 27, 2017

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

Update: Some offers mentioned below are no longer available. View the current offers here.      

Want to see the latest flight deals as soon as they’re published? Follow The Points Guy on Facebook and Twitter, and subscribe to text message alerts from our deals feed, @tpg_alerts.

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. 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.

West Coast, Best Coast, right? Find out for yourself this fall with cheap flights to Los Angeles (LAX) and Portland (PDX) from both Chicago or Boston (and vice versa). The cheap fares are available on American and United from late October through early November for as little as $98 round-trip. Do your research on Google Flights and then you can complete booking through an OTA like Expedia or Orbitz.

Airlines: American, United
Routes: ORD to LAX and reverse, BOS to PDX
Cost: $98+ round-trip in economy
Dates: August — November 2017
Booking Link: Orbitz or Expedia 
Pay With: Chase Sapphire Reserve, Citi Prestige (3x on airfare) or Chase Sapphire Preferred (2x on travel)

Here are a few examples of what you can book:

Chicago (ORD) to Los Angeles (LAX) for $98 round-trip on American:

Screen Shot 2017-07-27 at 1.40.49 PM

Los Angeles (LAX) to Chicago (ORD) for $98 round-trip on American:

lax-ord 98

Chicago (ORD) to Los Angeles (LAX) for $98 round-trip on United:

Screen Shot 2017-07-27 at 1.33.53 PM

Los Angeles (LAX) to Chicago (ORD) for $98 round-trip on United:

Screen Shot 2017-07-27 at 1.37.49 PM

Boston (BOS) to Portland (PDX) for $136 round-trip on American:

Screen Shot 2017-07-27 at 1.48.23 PM

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 (3x on airfare) or the Chase Sapphire Preferred (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.

If you’re able to score one of these tickets, please share the good news in the comments below!

H/T: Secret Flying

The All-New United Quest℠ Card

WELCOME OFFER: Up to 100,000 bonus miles


CARD HIGHLIGHTS: 3X miles on United® purchases

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

Apply Now
More Things to Know
  • Earn 80K bonus miles after you spend $5,000 on purchases in the first 3 months your account is open. Plus, an additional 20K bonus miles after you spend $10,000 in the first 6 months
  • $250 Annual Fee
  • Earn 3X miles on United® purchases, 2X miles at restaurants, on select streaming services & all other travel, 1X on all other purchases
  • Earn 3X miles on United Airlines purchases
  • Earn 2X miles at restaurants and on select streaming services
  • Earn 2X miles on all other travel
  • Earn 1X mile on all other purchases
  • Each year, receive a $125 credit on United® purchases and two 5k-mile anniversary award flight credits. Terms apply.
Regular APR
16.49% to 23.49% Variable
Annual Fee
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent, Good

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.