Chicago: Patios + Drinks = Why we live here in the winter

Common question: “Why in the world do you live in Chicago?  It’s so COLD!”

Common Chicagoan response: “Because the summers are the best.”

A huge reason for why Chicagoans choose to BE Chicagoans is because the summers are on point–beach weekends, twice-weekly fireworks shows, neighborhood festivals every weekend, outdoor concerts, you name it…we’re going to it!

One of my absolute favorite things to do in the summertime is hang out on a patio with a cold beer and great friends.  Check out some of my favorite patios and rooftops in the city for some sunny and boozy fun:


A West Loop newbie, Federales boasts a huge patio with some of the most fun and vibrant people watching I’ve seen.  The margaritas are flavorful and tangy, with an option to make it spicy, and the taco platters are enormous and easily split among a couple of people.  Bonus–when you order a shot in an ice glass (yes, the shot glass is made of ice) you get to throw it across the patio to try and ring a bell at the other end.  Who doesn’t love throwing thing?!

wp-1468337219878.jpgSaint Lou’s Assembly

So here’s the dealio: when you RSVP to Saint Lou’s Assembly’s Sunday summer events, you get to kick it on a gorgeous patio and drink from a keg for free until it’s empty!  No, I’m not kidding.  Each week, Saint Lou’s hosts a cool food event–pig roasts, fish frys, you name it–and a guest brewery stops by with a fresh keg for all to consume.

Free beer.  Go there.

wp-1469040460628.jpgWhiskey Business

Be still my 90s heart.  This Wicker Park newbie is on POINT.  The 90s themed Whiskey Business offers a TON of, well, you guessed it…whiskey, as well as creative cocktails (the Drew Berries-n-more anyone?), frozen daiquiri goodness, and an honest-to-goodness French Fry Bar!  This rooftop is absolutely gorgeous, with tons of seating, TVs, and a super cool vibe that lets you escape to a different time.

 Tiny Hatt

Yes I know, I’ve talked about Tiny Hatt before but there’s a reason–it’s a fantastic outdoor experience.  Check out this Riverwalk space for some delish sliders and deviled eggs, cool cocktails, and beautiful views of Chicago.

 Green Street Smoked Meats

One of my very favorite Chicago meat-lovers establishments, Green Street Smoked Meats offers a rustic-chic patio space with a cafeteria style restaurant experience.  Head on up to the counter, order your brisket and ‘tater salad (seriously, the brisket is TO DIE FOR) and take your tray out to the picnic benches for one of the best meals ever.


For an easy and chill sports bar experience, Hopsmith offers upscale bar food and dozens upon dozens of beers in a semi-enclosed rooftop space.  Head upstairs of Hopsmith for a bright and lively day of drinking while watching your favorite team (ahem, Cubs…) win.  I recommend the mac n cheese, the ginormous mozzarella sticks, and the pork belly lollipops (just look at Eric’s face, gazing longingly at the marinated goodness…)

Movies in the Park

OK so not a bar or patio per se…but drinking outside in the heart of the city ain’t too shabby amirite?  Grab your gals, bring some drinks and snacks, and watch some cinematic favorites in dozens of parks around Chicago.

wp-1468337620940.jpgBernie’s Lunch and Supper

One of my favorite newer places in Chicago, Bernie’s Lunch and Supper has the cutest rooftop area with fantastic happy hour specials that include sangria, draft beers, Moscow mules, and more.  A bit off the beaten path in the River North neighborhood, Bernie’s also offers a delicious menu that includes brunch classics such as frittatas and French toast, and dinner items such as roasted chicken, scallops, and falafel.


wp-1468337697212.jpgThis chic foodie haven has it all–gorgeous ambience, a lively atmosphere, creative cocktails, and fantabulous food!  Check out Fremont’s upstairs area for their retractable rooftop party spot.  You’ll love the bright, beautiful views, the comfy lounge areas, and the awesome service.  Make sure to try a variety of things from their food menu too; I’m in love with the Waffle Cheese, Brussels sprouts, and Giant Pepperoni and Whipped Ricotta Flatbread.

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