When the sun sets on December 21st (probably sometime right after lunch), it’ll officially be the start of the longest night of the year... and what we like to call the "Best Night of Your Life". Why? Because you’ll be spending it enjoying the fun-est nightlife the city has to offer, thanks to our recommendations on everything from the bestest happy hours, to the most epic dive bars, to today's contribution: nine of Chicago's raddest spots for late-ass eating and drinking. Check out the picks below, and make sure to map out the perfect evening with our itinerary builder.
Wicker Park and Wrigleyville
There's no better way to soak up booze 'til 2a than
late-night pizza late-night pizza topped with mac 'n cheese. Which they have at Dimo's.
If you love cold brewskis and country music, head to this Uptown gem for all the $3 cans of Hamm’s and George Strait songs you can shake a cattle prod to. The late-night crowd hits its peak around 230a, and doesn't really slow ‘til the cows come home (possibly with you).
The Hangge Uppe
This late-night fun house includes two all-request DJs, three dance floors, and five themed, full-service bars split between two floors. Our advice? Hit Lou Malnati’s Gold Coast for a late pizza dinner, then make the one block trek to dance off all those deliciously cheesy calories.
Pick Me Up Café
With almost around-the-clock hours of operation on the weekends, this is the perfect joint for post-bar noshing. Get the Special Pizzadilla (yup, a pizza/quesadilla hybrid), take a nap, and then come back for a hangover-curing Eggs Benedict breakfast.
After a long night of shooting Malort at Quencher’s Saloon, all your night needs to round things out is a juicy, Chicago-style dog and a heap of hand-cut fries. Get yours at this glorified wiener shack in Bucktown, which's open 'til 5a (!) on Fri/Sat. Just make sure you bring your booze jacket when the weather’s cold, 'cause it’s outdoor seating or bust.
Ditch those regrettable Taco Bell splurges in favor of quality, made-from-scratch Mexican grub at this tiny, open-'til-4a-on-the-weekends Logan Square eatery. Try one of their signature gringos with al pastor/Chihuahua cheese in a tortilla with a side of rice and beans, or $2 carne asada tacos.
Stout Barrel House
This Downtown beer hall is open hours beyond its neighborhood counterparts, and cooks up elevated comfort-fare like 'animal fries' with white and yellow cheddar, bacon & short rib, until 3a. If you’re still hungry after some on-site munching and closing time is drawing near, buy yourself a to-go pack of 30 Stout Sliders.
Where great barbecue and blues music meet, you’ll find this legendary, laid-back, late-night landmark. Grab a basket of juicy ribs to gnaw on, a pack of friends to converse with, and enjoy it all, plus music, ‘til the doors close at 4a.
Ideal for carnivores and masochistic eaters, roll up to this burger joint 'til midnight for one unforgettable post-drinking challenge: The Slinger. The Man v. Food-esque burger comes with two beef patties, two fried eggs, cheese, hash browns, onions, chili, a side of toast, and a commemorative certificate if you somehow manage to make that burger your bitch.
1. Dimo's Pizza Wicker Park1615 N Damen Ave, Chicago
2. Carol's Pub4659 N Clark St, Chicago
3. The Hangge-Uppe14 W Elm St, Chicago
4. Pick Me Up Café3408 N Clark St, Chicago
5. Red Hot Ranch2072 N Western Ave, Chicago
6. L'Patron Tacos3749 W Fullerton Ave, Chicago
7. Stout Barrel House & Galley642 N Clark St, Chicago
8. Kingston Mines2548 N Halsted St, Chicago
9. Diner Grill1635 W Irving Park Rd, Chicago
Dimo's Pizza's Wicker Park location is bigger than the original Lakeview one, has got $1 slices with certifiably crazy toppings, and a beer menu of local and season drafts and cans.
Carol's is an old-country, Southern-esque dive bar that has swingin' live bands, line dancing (impromptu, with special appearances by Carol herself), and cheap brews.
Getting lost in a bar may never have been so fun. As a Chicago staple for more than 30yrs, this massive dual-level dance haven offers five differently themed bars, three dance floors, and a variety of '50s through '80s rock and disco on one floor and modern hits on another. With drink specials galore and a pair of all-request DJs, we dare you not to break a sweat at the Hangge-Uppe.
Pick Me Up is Chicago's finest late night establishment (their cheese fries are something to write home about... trust us).
Chicagoans love their dogs hot and Red Hot Ranch's blinking red arrow sign directs them to this cash-only standby for "Depression Dogs:" Vienna beef dogs with mustard, onion, relish, sport peppers with a fist full of french fries in the bun. The natural-cased weiners pop when you bite them and the fries are crisp. Thin-pattied double cheeseburgers satisfy, but when in the dog house, get the dog.
If you thought you could only get decent Mexican street food south of the border, think again – for Chicagoans, it’s as easy as a trip to Logan Square. The market-driven menu at L’Patron includes highlights like carne asada and the signature la gringa, a tortilla with al pastor, Chihuahua cheese, pineapple, and a side of rice and beans. While seating is available, this counter-service taqueria is a lunch hotspot, so get there early to snag a seat and chow down.
Serving Southern hospitality in the heart of River North, Stout Barrel House & Galley serves up adventurous comfort food in an inviting, communal environment. A wealth of craft and draft beers assures that your stiff drink is as gustatorily satisfying as the exquisite food.
Kingston Mine's got two stages, top notch musicians, and awesome acoustics.