Cheapest Diners

(credit: Justin Sullivan/Getty Images)

What constitutes a dive these days? So many venues reach to be authentic, and will import old furniture, bring in a pre-1987-only jukebox, or even stock Jeppeson’s Malort just to get some divey charm. But is it just the age? The clientele? Cheap prices? Whatever the formula is, these dives and diners have a selective charm that many have found and loved. And a true dive bar never would never want to be a buzzed-about destination – so visit with respect!

California Clipper

1002 N. California Ave.

A fine old-timey bar refurbished for the modern era (but only slightly). The huge space is suitable for movie screenings, the back room is great for board game nights, and the grape soda on tap will let you and the bartender come up with some truly (in)famous cocktails.

Hollywood Grill

(credit: Hollywood Grill)

Hollywood Grill

1601 W North Ave.

The clientele at this longstanding 24-hour diner are what help it survive as a dive (the owners also run former Maxwell Street staple White Palace Grill and the new Plymouth downtown). Off-duty cops, hungry refugees from The Hideout and Exit, and the occasional drag queen make for wild nights – and the skillets aren’t bad either.

Hungry Brain

2319 West Belmont Ave.

An exception to the rule, Hungry Brain is something of a brainy dive bar. Playing host to poetry readings, jazz performances and improv comedy, The Brain has more in common with a coffee house than a pool-table-and-darts joint. Of course, the most important thing is that they serve beer, and if you’re in the mood to enjoy one out on the town – but still on a couch – The Hungry Brain might be the place for you.


491 N Milwaukee Ave.

Positioned on the wedge of Grand and Milwaukee, Richard’s has a uniquely shaped space filled with beyond unique characters. Salty snacks and octogenarians are behind the bar; an old-school jukebox and a beyond-random cast of regulars are in front of it. There’s usually a friendly crowd, so be prepared to talk to all of them – including the girl in the gold spandex, the Vietnam Vet who wants to dance to Tina Turner, and a friend you weren’t expecting who’s just as bowled over as you are.

Diner Grill

1635 West Irving Park Rd.

Diner Grill is a timeless, Nighthawks-style 24-hour single-counter diner. On the other hand, Nighthawks looked a bit classier, and definitely didn’t have the Slinger. For $7.50, you can order possibly the greatest calorie-to-dollar deal available in Chicago: hash browns topped with grilled onions, two cheeseburgers, and a blanket of chili (with giardinera available for the truly bold). Eating one of these monsters will net you one rumbling stomach later, but you’ll also get a certificate to remember (or lament) your feat.

Dan Morgridge is a writer in Chicago’s Ukrainian Village. He enjoys eating and drinking above his means, finding new music, and socially conscious hedonism.
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