5 Summer Sips not to miss

Pendrinks2unnamedSummer wine, or beer or cocktail wind down – don’t miss these 7 Outdoor Summer Sips in Chicago.

Don’t let the summer slip by without spending some time at one of Chicago’s freshest outdoor bars and / or an aAl Fresco dining spots.

Here are 5 not to miss; they are all very different, so I promise there is one here that will wet your whistle. You will find a variety of lively, engaged and interesting bartenders, selection of cocktails, cool atmospheres, and friendly faces.

Some of these places are just off the street others you have to take an elevator up to the spot.

The Whistler located at 2421 N. Milwaukee Ave, this spot is ever changing. Parking is easy to find.  When you walk in you might wonder, is it a gallery, record label, live music or DJ venue?  Yes, all of the above and more. The menu is always changing  the cocktails cleaver, creative it’s a never miss with a constantly changing selection of food and drinks. Small, cool and intimate a great spot to spend a few hours getting to know a new friend, or reminiscing with old friends. To the patio and enjoy the night


Cindy’s – This is a take the elevator up spot.  Located inside the Chicago Athletic Association at 12 S. Michigan 13 floor. You will wait, you will pay, you will enjoy. This is a very popular spot because of its location, selection of drinks, boozy popsicles, and solid good food, and that will help you to forget the wait, the cost, and maybe sitting close to or on top of someone you don’t know.

Atmosphere that’s open, relaxed, comfy, and loud and go for the view, bring a big wallet, and don’t worry if there is a lull in the conversation because the panoramic views of the lake and the park will be more than enough. They have a nice selection or drinks and lots of specials to keep you happy and coming back for more. Step outside enjoy the view, the firepit, the people and drink.

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Shanghai Terrace– This is a take the elevator up and be taken away to a quite elegant outdoor terrace. It’s furnished classy, and the food is some of the best in town. The summer drinks are special, light, tasty, classic, and flavorful. It’s located on the fourth-floor right outside of Michigan Ave, so you look around and you will see buildings surrounding you but not on top of you. This is a must stop spot over the summer, but they also have activities year round that will keep you looking forward to the next visit and menu at Shanghai Terrace – sit outside and listen to the traffic below it’s a low hum that add’s to the vibe.

Queen Mary 2125 W. Division St This off the street on west Division might be missed until you look up and see the crown. The name is not the story you think, and once there you can learn more. You may feel like you have walked into a British maritime throwback, it’s cozy, dark, friendly, and inviting. Outside on the sidewalk is the patio with table and standing rails. It’s a great place to grab a beer, or go with a rum, scotch, gin, I had the bartender whip me up something that warmed my insides and tasted great.


The WALKIN – 2727 N. Milwaukee Ave. Chicago, IL This is very cool, it’s connected to the liquor store – Red Star liquor and it’s kind of like walking from the store into their “Walk In”  cooler. The staff is half the fun; they are knowledgeable, friendly, creative, and low key. Their creative flow when they create the drinks served on the menu. They will customize your drink, and offer off the beaten path recommendations. The atmosphere is classy, low-key, and inviting. They don’t cook the food there, but you can get food from two nearby taverns Cafe Con Leche and The Harding Tavern. and have it delivered over to you. It’s dog friendly. Has a great vibe the night we sat there it was as cool outside and inside – sit near the street for great people watching.

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