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 that 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.Start your day off right by booking a great round-trip deal to the Windy City this fall. Fly out of New York’s LaGuardia Airport (LGA) to Chicago O’Hare (ORD) from just $99 on American — note that you can originate in Chicago as well. The best flights seem to depart on Wednesdays and return the following Tuesday or Wednesday, so check with Google Flights for the dates that work best with you. Once you’ve found a flight, book directly through American or through an OTA such as Orbitz.Airlines: AmericanRoute: LGA to ORD/ORD to LGACost: $99+ round-trip in economyDates: Many Wednesdays from October through December 2017Booking Link: ExpediaPay With: The Platinum Card from American Express (5x on airfare), 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:Sign up for our daily newsletterEmail addressSign upI would like to subscribe to The Points Guy newsletters and special email promotions. The Points Guy will not share or sell your email. See privacy policy.New York (LGA) to Chicago (ORD) for $99 round-trip on American:Chicago (ORD) to New York (LGA) for $99 round-trip on American:Maximize Your PurchaseDon’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 Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.H/T: The Flight DealIf you’re able to score one of these tickets, please share the good news in the comments below!
