Insiders Guide to Dining & Drinking: Summertime in Chicago

City Winery Chicago RiverwalkIt’s common knowledge that summer is the best time to live in, and visit, the city of Chicago; but, how do you narrow down the dining and drinking options with so many differing opinions? We decided to skip the noise and go right to the source, six wine professionals who eat, sleep and breathe the Chicago dining scene. Below are their recommendations for where to drink wine, have a beer (or cocktail) and where to eat when the weather gets nice in Chicago. Let us know our favorite spots in the comments below!

Favorite Chicago Spot for a Glass of Wine in the Summer

Diana Hawkins

Other than my backyard?  Hopleaf. Yes, the beer bar. My friends will be mad at me for sharing this, but their wine list is full of insane deals. They straight-line all their pricing so it’s $35 for white and $45 for red – yes even for that 2003 Lopez de Heredia Tondonia Rioja or Guigal CDP. With a killer patio, great food, and beer to cleanse your palate, it’s the perfect spot.


Ryan Arnold

I hate making decisions when I go out so I appreciate a small, well-curated list and knowledgeable staff. Rose on the patio at Mon Ami Gabi in Lincoln Park is the place to be for summer wine time!”


Liz Mendez

I like Table, Donkey & Stick because I’m not a huge fan of sitting on street side patios, they have a fantastic garden behind the restaurant and I love the entire wine list, so you really can’t make a bad choice with any wine by the glass.


John Lenart

For a great glass of wine, you can’t beat Terroir Tuesday’s at Table Donkey and Stick (2728 W. Armitage.) Each Tuesday proprietor/sommelier Matthew Sussman opens rare, hard to find, or older vintage wines and sells them by the glass at his cost! Amazing wines, amazing deals and a fun outdoor patio.


Rachel Driver Speckan

Leña Brava New and refreshing! Leslie brings a pop of vibrancy to the wine list and the by the glass options are fun, lovely with food, and crushable.



Charles Ford

Wine is a tough one because my favorite spot to enjoy a nice bottle is my back porch, truly there is nothing more pleasurable.  But when it’s time to go out and pick a bottle or glass off the list my first choice is Le Bouchon, on a Monday for lunch.  Le Bouchon is the best Bistro in Chicago. Popping a Chateauneuf-du-Pape Blanc and smearing escargot in herb butter on baguette is one of life’s most precious treasures to me.  It’s like medicine to my soul.

Favorite Chicago Spot for a Cocktail or Beer in Summer

Charles Ford

For a beer, my absolute favorite place is the Map Room.  Nothing but fantastic rotation after fantastic rotation of fresh, crisp, and delicious beers.  Just FYI, they now take credit cards and also do cheese and beer flights!  My favorite combo is still a few pretzels and Tripel Karmeliet or two…or three, and a Malort.


Rachel Driver Speckan

Libertad Due to my slightly suburban living location, I hit up Libertard fairly frequently. The cocktail list is smart and balanced with an innovative twist.” 



John Lenart

When it comes to beer I’m a traditionalist. Resi’s Bierstube (2034 W. Irving Park) features 13 traditional German beers on tap and more bottles, from Alt to Weiss than I can count. Top off the great beer list with Chicago’s oldest post-prohibition beer garden. Add in great German food from the postage stamp sized kitchen and what you’ve got is truly gemütlichkeit.


Liz Mendez

I’m not the biggest fan of hot weather (I know, I know) so I like to hit spots where the beer and cocktails are cold and the room is colder. I love to grab drinks and a snack at the Izakaya at Momotaro. It’s got a great speakeasy feel and the food, beer, drinks and sake are great for a hot summer night.


Ryan Arnold

Umm does Cider count? I’m frequently wined out since I’m surrounded by it all the time and beer has been making me lethargic. I can’t get enough of cider. Energy, tart acid, slightly fizzy, what’s not to like? Check out the Northman in North Center.


Diana Hawkins

The bars I like aren’t really that summery. So, once the weather breaks, I honestly just like being able to bike down California and get in trouble at The Continental or head down Western to grab a beer and catch a show at The Empty Bottle.


Favorite Chicago Spot for a Summer Meal

Liz Mendez

Since many summer nights are spent either working or cooking and barbecuing with friends, my favorite summer meals are lunch or brunch. Naha is hands down my favorite spot to have lunch in the city. The room is gorgeous and a perfect complement to Chef Carrie Nahabedian’s cooking and a glass of Champagne or Riesling.


John Lenart

I know this opinion isn’t a popular one but I’m not a fan of sidewalk “patios.” Why do I want to sit on the street with buses driving by, belching their exhaust as I try to enjoy a meal?  For me, summertime dining is all about the chef’s ability to take advantage of the bounty of the harvest. Perhaps nobody in the city does that better than Mark Mendez at Vera (1023 W. Lake). Mendez sources some of the finest produce and applies his no-nonsense approach to Spanish cuisine and what he turns out is simply fantastic. Add to that a great wine list and what’s quietly becoming one of the city’s best somm teams headed up by Christy Fuhrman and you’ve got a great meal. Go! Eat there now!


Rachel Driver Speckan

Monteverde Simple, real food with thoughtful preparation and love of cooking that you can taste. Brings the concept of wine on the table as the norm to life.”



Ryan Arnold

“Love Lula Cafe for Monday brunch/late lunch. Logan square is my favorite hood and the patio there is epic. Jason’s cooking tends to be fresh and light so I feel great after eating there too.


Diana Hawkins

90 miles Cuban Cafe. It’s down the street from me and BYO. They have a giant patio, good eats, and there’s rarely a wait; plus, there’s live jazz on Wednesdays.  Pro-tip: Grab Mosse’s Magic of Juju Chenin Blanc from Red & White for a perfect plantain paring. 


Charles Ford

Table, Donkey, and Stick is the truth.  The done truth for summer meals and most of my dining out experiences in the city.  This place has arguably the best charcuterie in Chicago. I always take a duck rillettes home with a loaf of their sunflower seed bread (when it’s available).  The restaurant is quaint, homey, and always welcoming.  I’m weak to resist their Monday night burger specials too.  I frequent this restaurant more than any other in Chicago for a reason.


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The Experts

Ryan Arnold Ryan Arnold | Lettuce Entertain You1466457488_snapchat_social_media_logo 1466457484_instagram_online_social_media1466457477_online_social_media_twitter

Ryan began his restaurant career as a member of the opening team for Lettuce Entertain You’s restaurant Osteria Via Stato in Chicago in 2004. In 2006 he began his foray into the importing world when he accepted a position with local Italian wine importer Vin Divino and quickly became their Regional Manager. He next joined Winebow, a large New York-based import company, and in 2010 was charged with opening their Chicago branch. Ryan returned to the hospitality industry two years later when he rejoined the Lettuce Entertain You team as Divisional Wine Director. In his current role, Ryan develops various wine programs for restaurants including RPM Italian, Paris Club Bistro & Bar and HUB 51. He also works with Corporate Purchasing to streamline, improve and individualize the wine lists company-wide.

Rachel Driver Speckan Rachel Driver Speckan | City Winery1466457477_online_social_media_twitter 1466457484_instagram_online_social_media

Rachel Speckan is the National Wine Director at City Winery. After many years immersed in the industry of all things boozy, Rachel is thoroughly dedicated to being the ultimate wine geek, with a good dose of sales savvy and super polished service and etiquette. She has traveled extensively, collecting vineyard rocks, eating local specialties, and drinking wine around the world in all the places.

With a special place in her heart for edgy California winemakers, dusty Italian reds, lush and stony Savennieres, and funky American microbrews, Rachel brings a dynamic, delicious, and well-balanced professional approach. Rachel is incessantly drinking wine, talking about drinking, encouraging others to drink, teaching about drinking, writing about drinking and eating adventures, drinking, tasting, researching, and talking about drinking. She is deeply entrenched in research and training in the Court of Master Sommeliers, as well as holding an Advanced Certificate from the WSET, and is also involved with the Cicerone Certification Program.

Charles FordCharles Ford | The Bristol 1466457477_online_social_media_twitter 1466457484_instagram_online_social_media

He began his career as a line cook at Jackie Shen’s Red Light Restaurant and, after three years in the kitchen, he transitioned to service and began bussing tables at Everest under the supervision of Dave Johnston, Chef Thierry Tritsch and Chef Jean Joho. In October 2011, after over a year at Everest, Charles followed Dave to The Bristol, where he joined the team as Assistant Manager. His commitment to excellent service was a natural fit at The Bristol, where hospitality to both guests and employees are of utmost importance. 

While continuing to find his niche in the hospitality industry, Charles became a Certified Sommelier with Court of Master Sommeliers. He is currently the General Manager and Wine Director, fulfilling his passion for creating memorable experiences for guests through both great service and exceptional wine. 

Diana HawkinsDiana Hawkins | Silenus & Me1466457477_online_social_media_twitter 1466457484_instagram_online_social_media

Diana Hawkins is a Certified Sommelier through the Court of Master Sommeliers. She grew up in Columbus, OH and went to college for engineering in Southern California. She quickly realized that studying math and science was best tempered with a teacup full of Sherry or a glass of Cabernet. After this discovery, she was off visiting nearby wine regions, such as Paso Robles & Santa Barbara, when time allowed (and even when it didn’t).

Once college was over, she moved back to Chicago to work in the corporate world, but never stopped learning about wine. After a poignant trip to the Columbia Valley, she quickly realized that corporate America was not her calling. She promptly quit and went to work in a wine shop in Wicker Park. Her mother thought she was crazy and would be back in a cubicle by the end of the month. But, she loved it and hasn’t looked back since. Diana has worked as a sommelier at City Winery, The Promontory and now runs the beverage program at Lula Cafe.

John LenartJohn Lenart | The Honest Pour | 1466457477_online_social_media_twitter1466457484_instagram_online_social_media

John Lenart is a freelance wine writer. His work can most frequently be read at and in Wine and Spirits Magazine. He’s also the host of the wine podcast “The Honest Pour.” In each podcast, Lenart interviews winemakers from around the world to help listeners make a connection to the people and places behind some of the world’s most exciting wines. Available on iTunes, Google Play and Stitcher you can find out more about the podcast at

Liz MendezLiz Mendez | Vera Restaurant1466457477_online_social_media_twitter1466457484_instagram_online_social_media1466457488_snapchat_social_media_logo

While financing her education at DePaul University, Elizabeth Mendez began to wait tables at some of Chicago’s most well-known restaurants, the passion of the food and wine bug hit, and Elizabeth never looked back. Gaining a reputation for her unwavering commitment to hospitality throughout the restaurant business, Elizabeth worked her way up through the ranks of the Chicago restaurant world from a server to Wine Director and now owner of her own restaurant, in Chicago’s red-hot West Loop neighborhood, Vera. On most days, you can find Elizabeth working the floor at Vera chatting with guests about her many passions between food, wine, photography and music.

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