I'm a steak sandwich type of guy myself but also like elakin and GWiv mention up above I don't like it when you have to wrestle with the sandwich. My all time great as far as steak sandwiches goes is from The Tornado Room in Madison, WI. I'm also a big fan of Mr. D's steak sandwich but always get the shish kebab sandwich instead of it. Also mentioned in here is the steak sandwich from el cubanito which is amazing and one of favorite sandwiches period. Well this past week I have tried a couple places where the steak sammy's came highly rec'd.
The first one comes from Bridgeport icon, Morrie O'Malley's, the seasonal hot dog stand located at 35th and Union and a favorite of the residents and White Sox fans from all over. It came highly rec'd by my buddy who's a narc in that area and knows good cheap food. They grill up (to your liking) a strip steak sandwich on toasted French garlic bread and its available with any of their toppings you want, but you gotta go with just the grilled onions. I had a tussle or two with the meat but it wasn't anything serious but the sandwich, now it was serious.

Morrie O'Malley's strip steak sandwich
The second sandwich I tried was from the legend that is The Brat Stop up in Kenosha. It came highly rec'd by GWiv as you can see above, so you kind of just know its good. Except it wasn't good, it was great. I am never able to order up anything else from Brat Stop except for my beloved Brats while sitting at the bar
(gotta get them at the bar) but now I have to have a brat and a ribeye steak sandwich each visit. It was everything described by Gary up above and perfect with a dash of A1 and a couple spoonfuls of fresh onions and the bun is key. When paired with a schooner of Spotted Cow it was one hell of a combo.

The Brats Stops Ribeye steak sandwich
Morrie O'Malley's Hot Dogs
3501 South Union Avenue
Chicago, IL 60609-1629
(773) 247-2700
The Brat Stop
12304 75th St
Kenosha, WI 53142
262-857-2011