Nonstop Flights: Chicago to/from Boston $79 r/t – American Basic Economy

[08/09/2018 @ 10:38 AM CT] Book this fare on: Priceline, Travelocity, Orbitz, CheapTickets, Expedia, Hotwire, BookingBuddy.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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American Airlines has “basic economy” round-trip flights from Chicago (ORD) to Boston (BOS) for $79, NONSTOP. $40 each-way. “Regular economy” is available for +$25 each-way. Midweek flights August to October on Mondays through Wednesdays.

Note: “Basic Economy” fares do not include a free carry-on bag. Only a small personal item, like a Jansport City Scout backpack is free. Checked bags cost +$25 each-way. Seats are randomly assigned prior to boarding. If you have an AAdvantage credit-card you can avoid bag fees.

Note: I’m currently using the Jansport Right Pack as my “personal item” when I fly in “basic economy”. Which is slightly more than expensive than the Jansport City Scout because its fabric is Cordura instead of Polyester. Both have the same dimensions which are: 18″ x 13″ x 8.5″. There is half-an-inch of extra depth than what is officially allowed by AA, but it has never been a problem for me. The bag has a large main compartment, which makes it ideal for stuffing as much as you can into the limited amount of space.

  • Example Dates: (Priceline / BookingBuddy) Aug 15 – Aug 22 / Sep 12 – Sep 19 / Sep 19 – Sep 26 / Oct 02 – Oct 10 / Oct 16 – Oct 23 / Oct 23 – Oct 30 / Oct 30 – Nov 06 / Other datesThere are more dates available than the ones we list here, experiment on your own.

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  • Tips: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.

I was able to pull this fare up on Priceline. Screenshot taken when this post was initially created. See timestamps at the top of this post.


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