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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 the 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.

You don’t need to travel thousands of miles to have fun, and if you’re looking for a great time, Chicago is a city that should definitely be at the top of your list. United is currently offering a fantastic deal, with flights as low as $70 round-trip from New York (LGA) and Boston (BOS) to the Windy City (ORD). It works both ways, too, so if you’re in Chicago, you can take a trip New York City or Boston from $76 round-trip, all taxes included. Availability is pretty open, as we’re seeing these kinds of prices through early December. Though the weather will be getting colder, all three cities are well worth the extra layers you’ll need to throw on.

Airline: United Airlines
Route: BOS and LGA to ORD
Cost: $70 round-trip in economy
Dates: October — early December 2016
Booking Link: Orbitz or Expedia
Pay With: American Express Platinum Card (5x on airfare), Chase Sapphire Reserve, American Express Premier Rewards Gold, Citi Prestige (3x on airfare) or Chase Sapphire Preferred (2x on travel)

Here are a few examples of what you can book:

New York (LGA) to Chicago (ORD) for $76 round-trip:

New York (LGA) to Chicago (ORD) for $76 round-trip.
New York (LGA) to Chicago (ORD) for $76 round-trip.

Boston (BOS) to Chicago (ORD) for $70 round-trip:

Boston (BOS) to Chicago (ORD) for $70 round-trip.
Boston (BOS) to Chicago (ORD) for $70 round-trip.

Chicago (ORD) to New York (LGA) for $76 round-trip:

Chicago (ORD) to New York (LGA) for $76 round-trip.
Chicago (ORD) to New York (LGA) for $76 round-trip.

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, American Express Premier Rewards Gold 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 Deal

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

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Chase Sapphire Preferred® Card

With great travel benefits, 2x points on travel & dining and a 50,000 point sign up bonus, the Chase Sapphire Preferred is a great card for those looking to get into the points and miles game. Here are the top 5 reasons it should be in your wallet, or read our definitive review for more details.

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More Things to Know
  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
  • Chase Sapphire Preferred® named a 'Best Travel Credit Card' by MONEY® Magazine, 2016-2017
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • No foreign transaction fees
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel
  • No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards
Intro APR on Purchases
N/A
Regular APR
17.74% - 24.74% Variable
Annual Fee
$0 Intro for the First Year, then $95
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent Credit

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