8258 W. Irving Park Rd.; 773-625-9840
$4.95 for sandwich + .50 for sweet peppers + .50 for hot peppers (pictured, above)
Don’t let the title fool you. Yes, Bob-O’s started as a literal hot dog cart/trailer (like Portillo’s) in the Northwest suburbs. But they also make their beef in-house, and they know how to slice it and soak it in jus just long enough without over cooking. My sandwich was jammed with beautifully tender beef covered with four fairly large strips of cooked green peppers and a knockout giardiniera of textural excellence: celery, cauliflower, carrots and sport peppers held together with plenty of oil. The pool of meat juice in my basket was a gentle reminder of what I could be doing with my hand-cut fries (which were among the best on the quest).
2932 W. Chicago Ave., Chicago; 773-486-9536
$6.00 for sandwich +.50 for sweet peppers +.50 for hot peppers
In business since 1949, this little joint occupying a triangular wedge near the Metra Line tracks does some serious beef. Mine arrived steaming hot, smooshed into a a soggy Gonnella loaf oozing with oregano and spices; the beef was as shredded and tender as Scatchell’s, but with more umami/savoriness like at Buona. Finally, someone besides Johnnie’s goes to the trouble of slicing their green peppers into thin, bite-sized shards, draping them just so, then piling on the homemade giardiniera of celery, sport peppers and carrots, dressed in a spicy oil that lingered for exactly five minutes on my tongue after I was done eating. Bravo, Mr. Boston.
3917 N. Harlem Avenue, Chicago; 773-283-7444
$5.50 for sandwich + .50 sweet peppers + .50 hot peppers
When I walked in, I saw the pics of Jay Leno and friends, so I figured this was connected to the Mr. Beef on Orleans, since they also have pics of the celeb. When I asked, the surly dude behind the counter said “Nope.” When I asked what was the difference, he replied, “we’re the one you go back to.” (The truth is, there is NO connection between the two). If you need some electrical work or construction, just come here at lunchtime to see all of the contractors stuffing their faces with beautifully cooked beef, almost disintegrated in a richly-flavored jus brimming with oregano and garlic. Sport peppers and celery are flecked with chili flakes for ample heat, while three big pieces of cooked green pepper add absolutely nothing to this sandwich. Sure, I would go back here (but I’d also go back to the other two Mr. Beefs as well).
215 W. Jackson Boulevard, Chicago; (312) 939-4204
$5.95 for sandwich + .45 sweet peppers + .45 hot peppers
This was, frankly, a surprise to me. My friend Andres, who came along on Day 2 of The Crawl, suggested it. Full of tourists on a Saturday afternoon, looking for deep dish and a beef, but taking all day to figure out how to order one, I asked for a “beef, sweet, hot, juicy” and unfurled one of the larger sandwiches on the quest. There was practically an entire green pepper (meh), steamed, intact, plus a giardiniera of feisty sport peppers and chopped celery seasoned with oregano. The sandwich was plenty big enough to share (I brought along an 8” serrated knife to make splitting easy), and the half I had was properly wet, messy, with the shredded, seasoned beef that lingered a few seconds on my palate after devouring each bite. I loved how the butcher paper was loaded with spices and drippings as I ate, and yet each bite wasn’t as hot as, say, Al’s, which could overwhelm you.
1079 W. Taylor St.; 312-226-4017
$5.99 for a regular sandwich; .60 for sweet; .60 for hot
This is one of the legends in Chicago. Started around The Depression, a result of those Italian “peanut weddings” where immigrants used the drippings and trimmings from expensive beef and made sandwiches out of them, dipping them to add heft (sounds like a debris po’ boy from NOLA), Al’s has one of the best spokespersons in the form of Chris Pacelli, a Chicaaago guy, dere indeed. I find the problem with Al’s – like Buona and Portillo’s – is consistency. Since they each have so many locations now, spread all over the place, the sandwiches you’ll find at one location rarely match another (see: Buona). I went to the original location on Taylor, in Little Italy, where my regular-sized beef came with 2 big hunks of bell pepper (yawn) and a giardiniera featuring just celery flecked with red chili flakes, giving the top of the sandwich an odd reddish hue. The beef (made in-house, unlike those little satellite franchises) was tender, pliable and shredded like Johnnie’s. There were hints of garlic and oregano and it was certainly dipped adequately. But the chew seemed a little off, and I couldn’t get past the giardiniera, or lack thereof, which was missing peppers, carrots, and more importantly, a good balance of sweet, hot and crunch. I realize this is probably closer to the form the original took some 80 years ago, but the sandwich as a whole doesn’t work as well as others in town, at least for me. (Side note: Mario’s ice across the street is as overrated as the parking meter deal the Daley administration negotiated. More like frozen chunks of hard ice, similar to the equally mystifying Ferro’s on 31st St., rather than the soft, smooth and slightly creamy versions at Scatchell’s and Johnnie’s).
666 N. Orleans St., Chicago; 312-337-8500
$7.00 for sandwich, includes peppers
This is another one of the legendary Founding Fathers in Chicago, having made the rounds on national TV and being BFFs with the likes of Joe Mantegna and Jay Leno. I do think one of the reasons for this is that when national TV shows/hosts come to town, they stay nearby and they don’t have time to schlep anywhere. Case in point: when I was a guest on “Food Wars” on the Travel Channel, I told the producers they had to go to Johnnie’s. They said there were tight on time, so Al’s on Taylor and Mr. Beef on Orleans were going to have to do. I digress. They still use top sirloin here, roasting in house, cooling, then slicing extremely thin each day and letting it bathe in the richly-flavored jus – which was among my favorites in town (I had written down “yum” in my notebook). My sandwich arrived with a strip of bell pepper and a hot giardiniera featuring celery flecked with chili flakes and sport peppers. They realize that you can’t let the beef sit too long in the jus, on the steam table, otherwise it will cook too much and get tough – a sign of experience. But my problem here was the size of the sandwich. Just too skimpy, and easily below the 4 oz. standard they shoot for. When I asked the owner about it later, he told me the guy who works on Saturdays tends to be more inconsistent than the weekday guy. “Come back during the week when he’s working here, and I promise it’ll be a little bigger; we’re still working with our weekend guy,” he told me. I think consistency is a huge issue in the beef community, as I had the same problem with a less-than-juicy beef at Buona, in Hillside: Mr. Buonavolanto himself (via his publicist) invited me back to the Berwyn location anytime to personally make me a “properly dipped beef” after he saw my Instagram post. (I didn’t take him up on it). But therein lies the conundrum: a great beef joint has to have a consistently great beef sandwich.