Deal Alert: Boston and New York to Chicago From $88 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 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.

Major US carriers are currently offering fares from the Big Apple and Beantown to the Windy City — and vice versa — for under $90 round-trip non-stop. If you have a choice in carrier, you're top pick would probably be JetBlue because they don't offer stripped-down basic economy options. We're seeing that most discounted American Airlines fares are also booking into Main Cabin (opposed to basic economy), so that would be a solid second choice. All of the discounted Delta and United fares book into basic economy. If you get stuck with a basic economy ticket, you can defeat many of its negative aspects by having airline elite status or a co-branded airline credit card. In some cases, you'll score the best deal by flying different carriers for your departure and your return so we recommend using Google Flights when searching for flights.

Airline(s): American, Delta JetBlue, United
Route: BOS/JFK/LGA to/from ORD
Cost: $88+ round-trip in economy
Dates: August - 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, Premier Rewards Gold Card from American Express, Citi Prestige (3x on airfare) or Chase Sapphire Preferred (2x on travel)

Here are a few examples of what you can book:

Boston (BOS) to Chicago (ORD) for $88 round-trip in September on JetBlue:

Boston (BOS) to Chicago (ORD) for $89 round-trip in July on American and JetBlue via Expedia:

New York (LGA) to Chicago (ORD) for $123 round-trip in October on American:

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.