Why queue up on the sidewalk just to spend an evening corralled in an overcrowded former service-station parking lot? We could give you a few reasons, but let’s start with the reasonably priced tacos ($3)—namely the famous pork-belly version, best washed down with a small-batch whiskey. Beyond the food, superb people-watching from the packed metal tables means gazing at neighborhood scenesters and Paul Kahan–worshipping foodies, as well as the parade of passersby on the bustling street beyond. RECOMMENDED: Outdoor alternatives to Big Star.
1531 N Damen Ave, (between Wicker Park and Milwaukee Aves)
You’re supposed to eat fish and chips in a musty pub for authenticity, right? Not come summer, and not when this Irish mainstay has a patio that’s a dead ringer for your rich friend’s parents’ place in the ’burbs. Big, fat, blooming flowers ring the high privacy fence, wrought-iron tables and chairs get shade from stylish umbrellas, and landscaped patches of grass just beg for crawling babies, your own toes or, on Sundays, an acoustic trio serenading with traditional Irish folk tunes while the crowd gets lit on Scotch. RECOMMENDED: Classic Chicago beer gardens.
3471 N Elston Ave, (at Addison St)
The gorgeous 18th-floor bar of the Raffaello Hotel boasts three prime sections: a handsome, dim interior full of tufted leather banquettes; a chic exterior deck lounge with open fire pits; and a narrow indoor-outdoor corridor where the marble floor and arched windows play against contemporary green stools. The addition of Aviary vet Craig Schoettler has brought seriousness to the cocktail program; we recommend the full-bodied Pineapple, in which a sprig of mint is dipped in Chartreuse and set aflame. RECOMMENDED: "The return of Craig Schoettler."
201 E Delaware Pl, (at Mies van der Rohe Way)
Duke of Perth
You’ll never know how relaxing Celtic music can be until you spend an afternoon at this Scottish ale house. Listen closely as you hang out on the serene outdoor patio, eating fish and chips (they’re all you can eat on Wednesdays and Fridays) and drinking from one of the best Scotch whiskey lists in the city—soon you’ll be humming along.
2913 N Clark St, (between Surf St and Oakdale Ave)
The Garage Bar & Sandwiches
When a bar boasts a rooftop deck, 66 beers and a menu of 20-plus sandwiches, it’s safe to assume it’ll also boast an obnoxious River North crowd. There’s nothing of the sort at the Garage, a pretense-free neighborhood hangout on the Northwest Side. Darts and shuffleboard provide entertainment on the industrial-ish first floor, while the mellow second-floor roof deck has plenty of tables and (so far) no need to fight for one.
6154 N Milwaukee Ave, (between Huntington and Hyacinth Sts)
Halsted’s Bar & Grill
Though it’s tucked away from the hustle and bustle of one of the flashiest streets in Boystown, there’s still plenty of man candy to help satiate your appetite at one of Lakeview’s biggest outdoor gems. Neighboring buildings provide cool shade, as do the cabana-esque ceiling fans. The bar fare is pretty standard, though the rich mac and cheese is sure to guilt anyone into a trip to the gym. Drinks are cheap: $3 mimosas and screwdrivers during weekend brunch and a killer $7.50 Ditka’s Bloody Mary. But what Halsted’s boasts in appearance it sometimes lacks in service—servers run around like chickens with their heads cut off when the patio is at capacity.
3441 N Halsted St, (between Newport and Cornelia Aves)
Handlebar Bar & Grill
This laid-back Bucktown messenger magnet feeds famished cyclists with internationally inspired veg food. Warm weather demands grabbing a seat at one of the shaded, metal patio tables and ordering from the well-curated selection of microbrews—or, better yet, a pitcher of tangy, refreshing housemade margaritas. Pretension is rare in the fenced-in yard—unless you count the high-end fixed-gear bikes that roll through the back gate (an in-yard rack keeps them secure).
2311 W North Ave, (between Oakley and Claremont Aves)
A gurgling goldfish pond, picnic tables galore and a lush lawn all around is the scene at this West Town dive. But when it rains (or at 11pm, when the garden closes), pack up the ciggies and head back inside, where the smell of whiskey and cheap beer hangs in the air, drunks angle for a turn on the Ping-Pong tables, and the jukebox coughs out the Cars and Madonna.
1059 N Wolcott Ave, (at Thomas St)
The J. Parker
On the one hand, the BOKA Restaurant Group’s year-round rooftop bar is unlike any other in the city: It boasts destination-themed cocktails, seasonal small plates from chef Paul Virant and sweeping, mesmerizing, breathtaking views of Lincoln Park from the 13th-floor roof of the Hotel Lincoln. On the other hand, it’s still a rooftop bar, which means on a gorgeous day, you might need to sacrifice your first-born just to get a seat.
1816 N Clark St, 13th floor, (at Lincoln Ave)
First, its virtues: Towering trees shade most of the enormous two-level garden at this 50-plus-year-old Edgewater institution. The straightforward half-pound burgers (no farm-fresh cheese or elk patties here) are a notch above average and taste like something your dad grilled when you were a kid. The beer is cheap: $11.25 for an Anchor Steam pitcher. But holy God, the service is pull-your-hair-out slow, and the servers, mostly indifferent twentysomethings or matronly ladies, rarely crack a smile. Our solution: Order multiple pitchers at a time and make no plans for the rest of the evening. You probably wouldn’t want to be anywhere else anyway.
5910 N Broadway, (between Rosedale and Thorndale Aves)
At seven stories, the garden at NoMI isn’t as high as some of the newer hotel bars in town. And yet this is still the premier place to get a drink above ground. Chalk it up to the Park Hyatt’s unparalleled service, or the snacks (if you can call pristine dishes like caviar and scallops “snacks”). The fact that the view isn’t all that exciting just speaks to the garden’s appeal—even on ground level, this place would shine.
800 N Michigan Ave, (between Chicago Ave and Pearson St)
From the shingled roof to the oompah music, this North Side fave is the place to get your Teutonic eat on. Many trundle in for the extensive collection of German beer but the food is sehr gut, too. The butter-soft smoked Thuringer sausage has a great mellow taste, while the Sheboygan brat makes a delicious mess with mustard and a heaping pile of sauerkraut. Make your own Munich with a stein of weiss in the back beer garden, where wrought-iron tables and bright flowers are enclosed by wooden privacy fences. RECOMMENDED: German restaurants in Chicago.
2034 W Irving Park Rd, (between Seeley and Hoyne Aves)
RM Champagne Salon
You enter through an unmarked alleyway, glowing strings of lights leading you to a cobblestone courtyard and ornate parlor that resemble a Parisian hideaway. You forget where you are. You order glasses of Champagne you’ve never heard of, you gently unhinge oysters from their shells, and when dessert comes, your selection is plucked from a fanciful cart, replete with bite-size macaroons and caramels and marshmallows. Heaven? Who needs it when there’s RM? RECOMMENDED: Chicago's new wine culture.
116 N Green St, (at Randolph St)
Roof at the Wit Hotel
Prepared to throw some elbows? Get in line. ROOF is the sexiest outdoor bar in the city, and you’re far from the only one who wants a piece of the action. But as long as you know what you’re in for, the crazy scene (and the crazy waits, which sometimes extend down the block) actually can be part of the fun, as long as the service doesn’t slack off, as it sometimes does. Once you’re finally planted on a cushy white couch, sipping on a fruity, fresh drink and feeling like an extra on Entourage, those hurdles will be far from your memory. RECOMMENDED: Outdoor alternatives to ROOF.
201 N State St, 27th floor
If the name didn’t tip you off, there’s a terrace attached to this upscale Chinese restaurant and lounge (and a mighty nice rooftop one at that). Thanks to piped-in world music, loads of greenery and just the right amount of breeze, it might even fool you into believing you’ve made a tropical escape from the city. (Well, after a few lychee-sake martinis or ginger juleps it might.)
The Peninsula Chicago, 108 E Superior St, (between Michigan Ave and Rush St)
Back before Lakeview (or much of Chicago, for that matter) gave a rat’s ass about craft beer, Sheffield’s began providing locals with a solid brew education. Today the mission is the same, to turn basic beer drinkers into better beer drinkers and keep the aficionados happy. Under the canopy of massive cottonwood limbs, the side patio feels lush and secluded, all the better for sampling through just about every style of beer known to man.
3258 N Sheffield Ave, (between Belmont Ave and School St)
Boystown's megabar is famous for its showtunes night, booze-laced slushies and, of course, its gigantic patio. Six big rooms inside are all packed with cute, frisky boys distracting themselves with the same three things: the videos on the wall, the drink in their hand and the ass in your jeans.
3349 N Halsted St, (between Buckingham Pl and Roscoe St)
Three Aces has the look and feel of a punky college bar. But because chef Matt Troost is rolling fresh pasta and frying pig ears in the kitchen, it’s hard not to pay attention to the food. The only thing that can steal your attention? The 140-seat patio.
1321 W Taylor St, (at Ada St)
You wouldn’t expect a burger called a “double fatty” (that’d be a whole pound of beef) to be made from organic ingredients, but then again you probably wouldn’t expect a biker bar to carry more than 100 whiskeys, would ya? Give in to your gluttony while wasting the night away on the rooftop patio.
501 N Ogden Ave, (at Grand Ave)
Singles looking for a classy spot love getting spiffed up in their slinkiest summer gear for a night here, where there’s always going to be plenty of green: on the outdoor patio and in their wallets. Pink martinis are de rigueur for the ladies, while the guys go for cocktails and the occasional Jäger shot to work up the nerve to chat up the hotties.
1983 N Clybourn Ave, (at Racine Ave)
After months spent huddling around fireplaces and shivering from inevitable bar-room drafts, you deserve a drink. Outside. With the sun beaming down, margarita in hand. Get the most out of our summer with our guide to the best places to drink outside, from rooftops to hidden gardens to precious sidewalk seats.
RECOMMENDED: Best things to do in the summer in Chicago