OyChicago blog

After several months of tumultuous and unpredictable weather, from the unforgettable snowstorm in late January to the periodic flood watches and warnings that carried us through most of spring, we have finally reached summer’s doorsteps. You know what that means: beer gardens, retractable roofs and outdoor BBQs galore!

Indeed, Chicago is ripe for some outdoor activity, and you can tell by the excitement and good feeling that permeated most of Chicago yesterday. As every Chicagoan awoke to a cloudless, beautiful, 80 degree morning, I bore witness to the Memorial Day beach and lakefront mobs that descended on Lake Michigan’s downtown beaches and outdoor cafes. I joined in the excitement as I passed Oak Street Beach and saw all the umbrellas, beach towels and volleyball courts packed with Chicagoans bursting with summertime energy. After much thought, I decided to create a list of restaurants, cafes, and places to be seen this summer in Chicago. Some are old favorites that will never see the fading sun, while the newcomers are sure to turn heads and create a buzz. So whether you’re in the mood for a fancy cocktail to sip outside or kibbitz with your friends at a chic rooftop lounge, I am sure you will find good times and sensational sips at any of these places!

Ari’s Favorite Summer Sips for 2011 (in no particular order)

• Piccolo Signo - Not enough can be said about this River West Italian gem. It’s one of my parents’ favorite places to take clients and family friends alike because of its amazing food, thanks to former Coco Pazzo executive chef Tony Priolo, who has truly created a Chicago gem year round. But it makes this list because of its virtually unbeatable outdoor patio setup.

• Big Star - If you haven’t heard of this Wicker Park playground, you better make your play-date arrangements now before the sea of hungry and thirsty Chicagoans pounce on the popular tacos and throw back some seriously tasty craft brewskis. Prices are reasonable and the food is outstanding, but what makes this place truly unique is its heavily sought-after outdoor seating. On busy nights with reasonably good weather, you can expect to put your name down and be prepared to peruse the Wicker Park neighborhood as you wait for that hostess to call you to your table. On the brighter side, at least you picked a trendy and chic neighborhood to eat.

• Terzo Piano - Just when you thought you would only venture to the Art Institute to check out some new and exciting exhibits, think again! Many Chicagoans have sung Terzo’s praises for quite some time, and there is no better time to echo those praises than now. I love the arts and will always promote and encourage skeptics to go see for themselves, but now I have another reason to send them there. So get up, go to the Art Institute, marvel at the amazing exhibits, then go treat yourself to a great meal, a gorgeous view and of course, some great weather.

• The Dock at Montrose Beach - This brand new eatery has caught the attention of many avid outdoor dining lovers simply by its word of mouth (which is how I came across it). It’s so brand new, it opened this past weekend and has yet to even update its website or upload a finalized menu. Even though I have yet to experience everything that is “The Dock,” I have my eye on this particular lakeside property and hope it lives up to the hype. As the sunny summer days approach, I would put this one on your list of places to satisfy your appetite.

• ROOF at the Wit - Two years ago I signed on to bartend at the newly-opened family style State and Lake Restaurant at the Wit Hotel, and while I don’t work there anymore, I still sing the praises of its chic, ultra hip counterpart ROOF. Two years later, ROOF is still one of the most frequented rooftop bars in the city, with its gorgeous views that span nearly 360 degrees, or its outdoor fireplace and floor-to-ceiling windows. The Mediterranean-style small plates will keep your tummy satisfied while you sip some deliciously original cocktail creations and marvel at how magnificent this city truly looks at night. There are alternative rooftop lounges that perch themselves on top of hotels and other downtown landmarks, but few offer the amenities that ROOF provides. It’s not everyone’s scene, but it sure hasn’t stopped Chicagoans from talking it up in the past and certainly won’t stop them now.

• The Wiener Circle - Yeah, I put it here. What, would you really object to having this notorious Chicago landmark on this list? Wiener Circle’s classic red wooden picnic tables accompany classic Chicago food—hot dogs, burgers and fries—for a perfect al fresco dining experience. Not to mention all the fun you’ll have watching the throngs of nighttime partygoers stumble and mumble up and down Clark Street. If you have one place to take a first time Chicago visitor this summer, day or night, take them here. They won’t regret it, admittedly enough, neither will you.

Some honorable mentions that nearly made my list of al fresco dining are: Citizen Bar, Duchamp, Nightwood, NOMI, C-View, Epic Sky, Volo, and Terrace at the Conrad. If you’ve got some great spots that I didn’t mention, feel free to add to this list.

So as you take a sip of that deliciously cold beverage, feeling the drops of condensation traverse your fingers on the glass, remember to savor every moment and enjoy every sip, because you never know when that doggone weather will take another turn for the worst.

L’Chaim!