West Coast flavors brighten the food at this taco-centric west-side taqueria and bar founded by the owners of Avec and Blackbird. Try the taco al pastor comes with spit-roasted pork shoulder and grilled pineapple, available until 3 a.m. on Saturdays and 2 a.m. the rest of the week. To drink, guests choose from 21 tequilas, nine mezcals, and dozens of bourbons.
Cheesie’s Pub & Grub’s cheddar-colored walls portend its grilled cheese-dominated menu. Named as one of CBS Chicago’s spots for “best grilled cheese,” Cheesie’s boasts 11 greasy, melty sandwiches, including one with homemade mac ‘n’ cheese cushioned between slices of Texas toast. The carb-heavy creations are best as a post-bar nightcap (Cheesie’s is open until 5 a.m. Thursday-Saturday).
Handlebar’s kitchen is only open until 12:30 a.m., but given its location amid Bucktown and Wicker Park’s bars and clubs, it’s the perfect spot for a snack during a neighborhood bar crawl. Vegan and vegetarian goodies such as black-bean tostadas and tempeh po’ boys are paired with craft brews on tap.
Quartino’s regional Italian tapas are surprisingly diverse—patrons can order anything from a veal meatball slider to chilled zucchini to gorgonzola dolce with apricot puree. The small plates, many of which are $6 or less, are served until 1 a.m. Monday-Saturday; on Saturdays, an additional selection of Neapolitan pizzas are available until 2 a.m.
It’s not hard to find a hot dog or pepperoni pizza after midnight, but how about a vegan tofu scramble? Not a problem at Pick Me Up Cafe. Open 24 hours Friday and Saturday and listed on Time’s piece on 10 Things to Do in Chicago, Pick Me Up serves several vegetarian dishes, including cinnamon-and-nutmeg spiced vegan french toast.
Open until 5 a.m. on Friday and Saturday, Chi Cafe looks like a mash-up between a 1960s diner and a colorful Asian cafeteria. Its seemingly endless menu can be intimidating to sort through, but diners are safe sticking to the flaming mini wok dishes, which sizzle with hearty piles of western-style oxtail or beef in satay sauce.
Use the change from your bar tab for a meal at the 24-hour Diner Grill—bacon cheeseburgers and grilled cheese sandwiches are each less than $3. The diner’s famous Slinger buries hash browns, grilled onions, cheeseburger patties, and over-easy eggs under a blanket of chili. Bonus: if you finish a Slinger in one sitting, you get a certificate of completion.
On Wednesday-Saturday evenings from 11 p.m. to 1 a.m., La Madia’s chefs prepare special prix-fixe meals from its Italian-centric menu. Six-dollar glasses of wine complement a multi-course exploration for two that might include gourmet Neapolitan pizza or handmade pasta.
For nearly 70 years, Jim’s diners have devoured the Maxwell Street polish sausage sandwich, a crunchy, sweet link smeared with yellow mustard, Spanish onions, and sport peppers. A UIC favorite, Jim’s serves its Polish and other timeless creations, such as a bone-in-pork-chop sandwich, 24 hours a day. Several sandwiches come with a free bag of fries.
Deal or no deal, our editors strongly recommend these businesses based on their reputation, popularity, and quality of service.