While the menus might justifiably play second fiddle to the ambience at these rooftop restos, we've handpicked our favorite nibbles & drinkables: from the bourbon, espresso, and pipe-tobacco cocktail at Homestead on the Roof to Frontier's big game gator broils.
With patio season well underway, restaurants are breaking out the string lighting and we’re breaking down Wicker Park’s top 5 rooftops, courtyards, and beer gardens for libation-fueled lounging. Read up, drink up, repeat as needed. You earned it this winter.
Ada Street | 1664 N Ada St
New American-Mediterranean meals & craft cocktails served in a chic candlelit space with patio.
A 45-seat dining room, an open kitchen flanked by a rugged concrete bar, a graffiti’d garage door opening to the back patio, and an astroturf-clad rooftop with exposed brick and string lighting just itchin’ for an upload. No filter.
With a drink list coming from a Drawing Room veteran, you’re in good hands. Personally, we’re suckers for the hand-bottled and carbonated mixers; namely, the picnic basket: Flor de Cana 7 yr rum, Lemonhart 151, ginger syrup, lime. For eats, we went with the korean-style short rib, baby bok choy, and napa cabbage. Stupid tasty. Then again, we shouldn’t expect anything less from a chef trained under Top Chef’s Tom Collichio. Our two cents? Throw in a ten-spot to thank the kitchen team with a six-pack and watch the short rib come out not-so-short after all.
Big Star | 1531 N Damen Ave
Gourmet tacos, margaritas and lots of bourbon fuel a lively hipster scene at this cash-only hangout.
To the left, a packed patio, string lighting overhead, sexy corrugated metal and a reclaimed wood bar. to the right, an old-timey order window & vintage yellow food truck slinging street tacos and horchatas. We’d advise you to arrive early, but frankly: there isn’t a time this place isn’t packed. Hence the monstrous expansion taking over the adjacent lot set for completion next year. Wait your turn, grab a seat, and don’t budge. Something tells us the stiff margarita pitchers will help with the last bit of advice.
Al pastor, braised goat, and braised pork belly street-style tacos, plus a weekly rotating special. The most ordered of all, however? The Taco De Pescado. A mondo hunk of batter-fried tilapia, cabbage, red onion, lime, and chipotle mayo. We threw a passing nod to the margaritas earlier but that simply doesn’t do them justice. A) You’re gonna want the pitcher. B) Nothing beats the namesake: ask for the Big Star, made with Lunazul Blanco, Vida Mezcal, lime, and Marie Brizard orange curacao. If you’ve got room for one more and are feeling a bit clandestine, cross the street to the block-long mural behind which the big star owner’s Violet Hour speakeasy beckons.
Homestead | 1924 W Chicago Ave
Rooftop restaurant, serving farm-to-table New American fare sourced from an on-site garden.
This rooftop resto above Roots Handmade Pizza takes the farm to fork monicker ever-so-literally, with a rooftop patio that overlooks their 1,000 square foot organic rooftop farm and two massive vertical hanging gardens. As for the interior, they got the rustic farmhouse aesthetic right with suspended factory windows hovering atop gorgeous distressed tabletops made from repurposed barn doors.
If we had a nickel for every time we heard you say you could use a teensy bit more rabbit meatballs and tobacco-bourbon cocktails in your life… Okay, so maybe not. But oh dear lord you’re about to find out what you’ve been missing. For a three-vice trifecta, order the the Weston, a bourbon cocktail with Dark Matter coffee essence coated in pipe-tobacco spray. For something a bit daintier, the Ink Sleeve (coupling mezcal with lime and bitters) has a block of raspberry ice for your spoon-shaving pleasure. For eats, we’re strong backers of the aforementioned rabbit meatballs for starters. The winner amongst the entrees? Smoked duck with wild rice polenta, pickled blueberries, and carrots.
Frontier | 1072 N Milwaukee Ave
Game, oysters & tap brews are served in a stylish lodge space with TVs, a fireplace & a beer garden.
Sure, it’s technically on Milwaukee but the vibe is distinctly more Montana. This Mountain West-inspired saloon is replete with mountaineer fixins: antler chandeliers swinging above pine/oak carvings & moldings, a majestic stone fireplace heating up the enormous timber-lined back deck, and a 40-foot reclaimed wood bar over which a 6-foot stuffed bear stoically keeps watch.
All-you-can-eat oyster boils (11 different types, no less), big game service (no, seriously, they’ll cook you an alligator), and whatever cajun switch-up Chef Jupiter feels like throwing your way (hint: the habanero/maple-reduction’d wild boar chop). Drinks-wise, now isn’t the time to get fancy. Frontier’s got 16 ice-taps of macros and micros, alike. There’s no going wrong. Except for IPA. Ick. One last insider’s tip: if you’re at a Chicago street fest, skip the nachos, and keep the eyes peeled for Frontier’s mint chimichurri-kicked lamb “Denver Ribs”. Though the Gator burger might be a better move if you’re concerned with keeping your fair-going outfit sauce-free.
Handlebar | 2311 W North Ave
Small, bustling neighborhood restaurant & bar serving seafood & vegetarian/vegan comfort food.
The quintessential biker bar. No, not the rolled up leather sleeve kind. We’re talking the rolled up denim pant leg variety. Aside from the divine vegan & vegetarian fare, the real draw here is the back patio. Grab a spot on a wooden bench, beneath an ivy-covered gazebo, amidst the peaceful backyard vibe in which the only reminder of north avenue traffic is… well, the sound of north avenue traffic. But even that lessens with each rustle of the tree cover overhead and each clanging of fork and knife. Which brings us to…
Made-from-scratch vegan comfort food. And no, wise guy, that’s not an oxymoron. For morning fare, they’ve got you covered with top-flight biscuits & gravy, breakfast burritos, and huevos diablos. For a palate-pleasing nightcap, we recommend the Country Fried Portobella with jalapeno cream gravy, mashed potatoes, collard greens, fried egg (or blackened tofu if we’re really doing the vegan thing). Only bit of bad news here? Only bike messengers get free fries. Looks like the coffee is about the only thing getting the fair-trade around here…