Deal Alert: New York & Boston to Chicago From $70 Round-Trip

Oct 19, 2016

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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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