Flight deals across the country from $258 on American and United

Looking for a cheap flight to or from Boston? This fall, several airlines are offering deeply discounted flights between Boston and popular destinations, including Chicago and San Francisco.

American Airlines and United Airlines sell fares from Boston Logan International Airport (BOS) for as low as $138 round-trip to Chicago O’Hare International Airport (ORD) and from $258 round-trip to San Francisco International Airport (SFO).

These fares are hundreds of dollars cheaper than regular prices, so if you’re planning a flight to Boston in the next few months, now is the time to make a reservation.

Subscribe to our daily newsletter

These discounted fares begin in September and are currently in effect on select dates through March 2023. Certain terms, conditions and limitations may apply to tickets. Read on for more details on booking and ticket classes.

For more TPG news and offers delivered to your inbox every morning, sign up for our daily newsletter.

Basics of the offer


Airlines companies : American (co-marketed with JetBlue) and United.
Routes: Boston to Chicago and San Francisco.
How to book: Search on Google Flights then book directly through American, JetBlue or United.
Travel dates: September to March 2023.
Book before: Although discounted tickets are available.

Related: An Insider’s Guide to 16 Boston Attractions

Examples of flights

All itineraries included in these discounted fares are nonstop flights to and from Boston. Flight times and date availability, as well as the fares themselves, are subject to change.

Boston to Chicago with United

United’s discounted fares between Boston and Chicago are for its base economy class tickets. This fare class incurs additional charges for carry-on baggage, seat assignments and checked baggage. Basic economy tickets also do not allow flight changes or upgrades.

But if you are a If you are a MileagePlus Premier member, have Star Alliance Gold status, or have booked the fare with an applicable MileagePlus credit card, you may bring one piece of carry-on baggage on board for free and check one piece of baggage for free even in economy class from base. Otherwise, expect to pay an extra $60 for the trip, or you’ll have to travel with just one personal item.


The example flight listed here takes place between Boston and Chicago during the first week of November. Most discounted fares are for Tuesday-Tuesday itineraries like this, but other date choices are also currently available.

According to Google Flights, the $158 fare listed here is an incredible $258 cheaper than regular flights on the route. That’s a saving of over 60%. Peak fares and vacation trips on this route can exceed $850.

Currently, you can still find reasonable flight times with these fares without resorting to red-eye or early morning flights.

Tickets for this fare begin on select dates in September and end in March 2023.

This fare is for United’s basic economy class, so again, unless you have miles status or are booking the fare with a United credit card, you will only need to travel with a personal item or pay about $60 more for the ticket.

Even if you have to pay the extra fare, that price is still a bargain – and a great one if you can take advantage of your baggage allowance status.

Related: How to Survive the Basic Economy on United Airlines

Boston to San Francisco with American Airlines

American Airlines, with its codeshare partner JetBlue, also offers deeply discounted flights from Boston. One of its best fares is $258 for a nonstop flight between Boston and San Francisco.

Like the United fare above, these prices are for a basic seat class that does not include carry-on baggage.


As shown in the Google Flights search results above, you can currently find round-trip tickets between Boston and San Francisco for just $258. This fare represents over $200 in savings per ticket compared to regular fares.

The shared flight between JetBlue and American Airlines offers two booking and pricing options. The JetBlue fare is for its Basic Blue economy seat class, which does not allow carry-on baggage on board. You will have to make do with one personal item that can fit under the seat in front of you. If you wish to bring a bag, an additional charge of at least $60 round trip will apply to your ticket.

The American Airlines fare for this route is $318, which is still nearly $150 cheaper than average. The US fare is for regular economy class seats, allowing carry-on baggage. The price is equivalent to booking the ticket via JetBlue with its baggage supplement. If you have American or JetBlue status or are booking with one of their credit cards, you may be eligible for free baggage allowance.

If you can travel without baggage or get free baggage allowance, this is a great rate for traveling around the country.

Related: JetBlue Basic Economy Supplements

Maximize your purchase

Don’t forget to use a card that earns bonus points on airline ticket purchases. Airline cards can still be a good call to earn status and rewards specific to those airlines, like for those flights using the Chase United℠ Explorer Card or the Citi® AAdvantage® Executive World Elite Mastercard®.

For more flexibility with earned points, The Platinum Card® from American Express Earn 5 points per dollar spent on airfare booked directly with the airline or through American Express Travel, up to $500,000 of such purchases per calendar year.

The Citi Premier® Card and the Reserve Chase Sapphire earn 3 points per dollar spent on airfare, while the American Express® Gold Card Earn 3 points per dollar spent on airfare when booked directly with the airline or through Amex Travel. The Chase Sapphire Preferred Card earns 2 points per dollar spent on travel.

Related: Maximize your airfare: The best credit cards for booking flights.

At the end of the line

Several airlines, including United and American, are offering discounted flights from Boston this fall through early spring 2023.

Round-trip tickets between Boston and Chicago for $158 and between Boston and San Francisco for $258 represent big savings on regularly priced flights. But when booking these fares, be sure to note your baggage allowance, as most basic economy seats don’t allow carry-on bags without paying extra.

If you can make the baggage allowance work for you (perhaps leveraging airline status), these fares become bargains. If you find an itinerary that suits you, book tickets quickly, as prices can change at any time.