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.
Top offers from our partners
How we chose these cards
TPG featured card
Rewards
10X | Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel |
5X | 5X miles on flights booked through Capital One Travel. |
2X | 2 Miles per dollar on every purchase, every day |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.Pros
- Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
- Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
- 10,000 bonus miles (worth $100 toward travel) each account anniversary.
Cons
- The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
- If you don’t travel frequently, this might not be the best card for you.
- Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
- Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
- Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
- Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
- Earn unlimited 2X miles on all other purchases
- Unlimited complimentary access for you and two guests to 1,300+ lounges, including Capital One Lounges and the Partner Lounge Network
- Receive up to a $100 credit for Global Entry or TSA PreCheck®
- Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
- Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
- Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023
Rewards Rate
10X | Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel |
5X | 5X miles on flights booked through Capital One Travel. |
2X | 2 Miles per dollar on every purchase, every day |
Intro Offer
Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel75,000 bonus milesAnnual Fee
$395Recommended Credit
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.740-850Excellent
Why We Chose It
The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.Pros
- Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
- Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
- 10,000 bonus miles (worth $100 toward travel) each account anniversary.
Cons
- The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
- If you don’t travel frequently, this might not be the best card for you.
- Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
- Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
- Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
- Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
- Earn unlimited 2X miles on all other purchases
- Unlimited complimentary access for you and two guests to 1,300+ lounges, including Capital One Lounges and the Partner Lounge Network
- Receive up to a $100 credit for Global Entry or TSA PreCheck®
- Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
- Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
- Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023