If you've shied away from dining at a steakhouse because of the price, head over to Fleming's Steakhouse for their "late night happy hour", which isn't all that late. Called "8 for $9 til 10", you can get 8 items for $9 each from 8-10pm. They also have a "5 for $6 til 7" which may be an even better deal, but the offerings are better for the later night menu.
The same deal is available at all Fleming's locations nationwide. Even better, at most Fleming's locations you also get happy hour prices on some drinks (8 wines and cocktails) including a flight of single malt scotches for $9! Alas, Boston doesn't allow alcohol happy hour (poor me) so I can only show you the food offerings.
First of all, even though you're only there for the cheaper food at happy hour, they still serve you the housemade bread - served with tomato basil butter and Chardonnay-infused gorgonzola sauce.
The $9 items that are offered are the same full size that you'd get from the regular menu and includes things like the Filet Mignon Flatbread (danish blue and monterey jack cheese, red onion confit).
The filet mignon was unusually tender for toppings you'd find on a flatbread. This is a steakhouse and it's filet mignon after all! This was probably my favorite of the things I tried.
For the $6 flatbread during the earlier happy hour, you get mushroom and artichoke instead of filet mignon.
I didn't have the stomach room to try everything and had to skip the prime burger, which I am sure would make a great affordable dinner if you get off work late one day!
Instead, that evening I tried the lobster lettuce wraps (North Atlantic lobster, crumbled bacon, crisped onion strings, orange-fennel slaw, tarragon dressing)
Ahi Tuna tacos on mini corn tortillas, ahi poke, wakame, radish-jicama slaw, creamy soy-lime aioli
Housemade burrata, charred grape tomatoes, wild arugula, toasted garlic crostinis
Short rib empanadas were also generously filled.
There are two desserts on the happy hour menu including a deconstructed Balvenie S'mores and Warm cinnamon-dusted donuts with fresh blueberry and lemon dipping sauces
I've found that Boston is not really a cheap city to eat in, with typically cheap foods like ramen or pho still running about $10 (versus $5-7 in LA), so this made Fleming's deal an even better value. You can eat pretty well for $9 (or $6 for the early happy hour) in a classy environment in Back Bay!
PS. The same prime burger is also on the early happy hour menu for only $6.
217 Stuart St
Boston, MA 02116