The Cute & Quirky: Kitsch’n on Roscoe 2005 W. Roscoe St
Far and away one of our favorites, Kitsch’n offers sweet nostalgia and delicious comfort food in a bite-size space bursting with retro goodies. Take a seat at one of the diner’s old-timey formica tables and, as you wait, entertain yourself and your tablemates with a magic eight ball and other blasts from the past. The coffee is delicious and the dishes straight-up classic American comfort food. You can’t miss with the grilled cheese or BLT, and trust us, you won’t want to pass on these crispy, curly fries.
The Old Fashioned: The Diner Grill 1635 W. Irving Park
In polite terms, this Lakeview eatery is a true blue, old fashioned diner. In other words, it’s a total dive, but it’s certainly not without its charms. Open twenty-four hours, the Diner Grill swells with late-night revelers on the weekends and caters to a far older set throughout the week. The food itself is standard diner fare: Vegetables are scarce, encouraging meat, eggs, and strong coffee to steal the show. While not a spot to frequent, The Diner Grill warrants at least a one-time visit, if only to soak in the simple qualities of a bygone era.
The Trendy: Little Goat Diner 820 W. Randolph Street
Take a seat at the counter of this bustling West Loop diner for a gourmet spin on American comfort food. From The Girl & the Goat’s Stephanie Izard, this spinoff serves up creative takes on your favorite dishes in an atmosphere that’s spirited, trendy, and busy round-the-clock. You can’t go wrong with any item on the menu, but we’d be remiss if we didn’t warn you that the smoked fries are not to be missed.
The Hidden Gem: Pittsfield Café 55 E. Washington
Tucked inside the lobby of the Pittsfield Building in the Loop, this little café is as classic as they come. Similar to the Diner Grill, the Pittsfield offers traditional American breakfast food—think piles of crispy hash browns, eggs any way you please, and stacks of perfect silver dollar pancakes. The staff is friendly, the food is cheap, and the atmosphere is a whole-hearted notch above its Lakeview counterpart. Sit ‘outside’ for a nice view of the Pittsfield’s attractive lobby. The hours are limited, but as no one seems to know this one exists, you’ll never find a wait to be seated.
The Over-Achiever: Glenn’s Diner 1820 W. Montrose
Glenn’s Diner would be an ordinary breakfast-all-day eatery, if not for the self-proclaimed ‘Best Seafood in the World’ moniker. With 16 kinds of fresh fish each day, Glenn’s has its roots in two unique worlds—fishery and classic diner. When it comes to the fish, the flavor combinations are creative. But where the fish dishes are at-times curious, Glenn’s breakfast and lunch are decidedly straightforward. For lunch, choose from diner favorites like an overstuffed meatloaf sandwich, or a grilled cheese and cup of soup. The breakfast menu boasts every kind of cereal ever made, in addition to eggs, pancakes, and waffles.
The Veggie Friendly: Chicago Diner 3411 N. Halsted
For any vegetable lover, the Chicago Diner on Halsted is your answer to the city’s comfort food. This Lakeview diner boasts mock creations of diner favorites, such as a reuben, a cheesesteak sandwich, and crispy fries piled high. The desserts are decadent and the shakes noteworthy. The diner even offers a selection of dairy products for those averse to faking everything. For a true diner experience, stick to the original location on Halsted. Logan Square’s version is delicious, but the atmosphere is cleaned up and modern, lacking the nostalgic feel of the original.
Have you sidled up to the counter at one of our diner picks around the city? Do you think we’re missing out on something? Tweet or Facebook to let us know! We’d love to hear from you.