Deal Alert: Boston and New York to Chicago From $88 Round-Trip
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 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.
Featured image by Sawyer Bengtson via Unsplash.
Sign-up Successful!
Welcome to The Points Guy!
Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.
With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.
- Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
- Earn 1X Miles on all other eligible purchases.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights.
- Fee Credit for Global Entry or TSA Pre✓®.
- Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees
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.
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.