Top Five Favorite Chicago Rooftops

Chicago is well known for beautiful summer days. With epic views the city rooftops create for some of summer’s most happening moments. With only so many summer days and so many awesome rooftops, I am sharing in today’s blog some rooftop recommendations that I think you must hit up this summer. 


On the rooftop of the Chicago Athletic Association is where you will find Cindy’s. The high energy, hip rooftop has views of Millennial Park, the water of lake Michigan and City landscape. The rooftop offers its patron’s a variety of eating options. From little bites to go with your favorite cocktail to a full-on dinner menu and yes even brunch (cause in the city brunch is absolutely the best meal of the day) anytime of the day is a great time to be at Cindy’s. Known for being one of the more favorite Chicago rooftops, you will find this place is filled with a lively active nightlife. The Causal sit-down dining during the peak season will require a reservation. I have enjoyed quite a number of summer night’s here at Cindy’s and if you too are the social extrovert, I’m certain you will as well.


A Tourist dream rooftop is located at Navy Pier. This opened in 2019 and is the world’s largest rooftop. The views of Lake Michigan and the city skyline are priceless! The rooftop offers both a full-service bar and dining menu. Offshore as described on their site is 36K square feet with an additional 20k of terrace and 7 firepits

Being a Chicago resident, I personally avoid the tourist trap of Navy Pier, but I had to check this one out when I had CA friends visiting me. Offshore is located at the very end of the pier – yes making for quite a walk. While I personally don’t find this ideal for an average weeknight of rooftop drinking, I would absolutely recommend checking this rooftop out when you have a guest visiting in-town or when looking for something fun to do during a summer weekend.


Like Trump or not this glam rooftop in Trump tower is exquisite in every way. Whether it be the views of the river running through the city or the legendary Wrigley Clock Tower, this rooftop makes for a perfect photo-op. Trump terrace offers both a full bar and dinner menu. With a very generous square footage this rooftop provides a space of intimacy for both large and small gatherings. The service is excellent, the space is luxurious, and that high standard is carried all the way down to the luxardo cherry that tops off your cocktail. 

One of the more personal reasons I enjoy coming here often is because Terrace 16 is in the heart of downtown walking and it makes for a very quick and comfortably safe walk home.  While I have so many fond memories here, a favorite recent was on a beautiful Friday afternoon this past May with a group of my girlfriends. Chicago is exceptionally easy to show-off to my suburban friends when I bring them to Terrace 16 


Chicago club is the oldest private club in Chicago. In order to catch these rooftop terrace views you must be a member or know a member. If you are fortunate to visit this terrace, I am telling you this will turn out to be a summer memory of a lifetime! The views of Buckingham Fountain, Soldier Field, the water of Lake Michigan and the city scape when paired with their incredibly delicious food and service is truly something that is unmatched! The Club rooftop offers both a full bar menu and full-service dinner. There are several firepits and outdoor couches for intimate gatherings as well as a fireplace. The Chicago Club brings a respect to the city dining experience with its high-class service and required dress-code.  This rooftop makes also for an exceptional place to host a private party as I experienced first-hand when we celebrated my husband Sean’s 50th in June of this year.


Being one of Chicago’s most popular summer hangouts, I probably don’t have to share too much detail about what makes this tri-level rooftop such a happening summer hot spot. London House is located on Waker Drive in the heart of downtown. To say the views are incredible would be an understatement. Pretty much every direction you turn their amazing! I would highly recommend if you are visiting Chicago (or are in town on business) to stay at London House. It is a well-respected hotel and many of their guests will enjoy a business dinner in their restaurant followed by an after drink on the rooftop. 

Being a favorite to Chicago, this rooftop will get very busy during the summer months – especially on weekends. The vibe of the crowd definitely makes this high energy setting one that will require a reservation if you want to be seated. The rooftop itself offers a full bar and the bar menu is geared more as bite-size appetizers as their full menu is found in their indoor dining restaurant. I personally enjoy ending a summer day with a nightcap on this rooftop. Last time I was up here was right as summer was coming to an end. The city was looking so beautiful that I had to snap a photo to preserve my thought on how Chicago during the summer months is truly is a dream playground.

There is nothing like a summer memory in Chicago to hold onto during those cold bitter winter months. I hope in sharing my favorite rooftops, you will not only make a summer memory, but it will provide for you a guidance to a great rooftop to visit when in the Windy City. I would strongly encourage you during the high peak summer season to call ahead of time to make a reservation as is required for most outdoor dining/rooftopsj in Chicago.


In celebration of father's day weekend I bring to you Dad-hood recipes, featuring some of One Life Kitchen (OLK) guests and staff who happen to also be really awesome dads. Creating a connection to the kitchen, I thought it be cool to not only share some of their dad moments/advice through a recipe format but also find out from the OLK "dad team" what their favorite food and drink recipe recommendation would be this Father's Day.



IN THE KITCHEN: Your perfect dinner would include what ingredient(s)? My wife and kids with a simple recipe

IN THE OFFICE: What is a key ingredient you believe is necessary to building a successful career? Be willing to work hard for what you want 

IN THE HOME: What is the one ingredient (aka) character trait you hope your kids see in you, that you would want them to also live out in their own life? Be firm, but fair


IN THE KITCHEN: The heart of the home is the kitchen – what makes you enjoy spending time in yours? The people in the family

IN THE OFFICE:  The time of the day you tend to be most productive? No question the early morning hours 

IN THE HOME: Share with us one of the ways in which you enjoy spending time with your child(ren).  Coaching their sports teams, traveling, nerf battles


Mixing Kitchen, Office and Home together, share one belief or truth that has enabled you to really live out your best One LifeWork hard, be nice, laugh a lot

MEET DR. DAVID CROSSON: Dr. David Crosson, or Dr. Dave as patients call him, is one of the expert chiropractors at ChiroFit who provides care to people of all ages in Barrington, Illinois. He strives to improve the well-being of everyone he has a chance to meet. 

Dr. Crosson contributes his time and chiropractic knowledge to humanitarian efforts in places as far away as Vietnam. He’s also involved with local charitable foundations, including the Northern Illinois Food Bank. He volunteers his time by providing risk assessment and functional movement screening for local fire, police, and city workers, and speaks to local high school students about health care and preventive wellness.

An avid golfer, Dr. Dave is married with two children and lives in Barrington, IL.



IN THE KITCHEN: Your perfect dinner would include what ingredient(s)? Conversation, laughing and sharing. After a long day apart at work or school, this is the time to come back together as a family and be in each other's lives.

IN THE OFFICE: What is a key ingredient you believe is necessary to building a successful career? Perseverance; nothing worthwhile is given to you so you have to work hard and when you hit a wall, it is critical that you NEVER give up. 

IN THE HOME: What is the one ingredient (aka) character trait you hope your daughter sees in you, that you would want her to also live out in her own life? Honor: be honest and always do what is right, even if it is hard.  Results matter more when they are achieved with the right means. 


IN THE KITCHEN: The heart of the home is the kitchen – what makes you enjoy spending time in yours? Being there with loved ones, whether it is preparing a meal or sharing in a conversation over milk and cookies. 

IN THE OFFICE:  The time of the day you tend to be most productive? Before standard business hours begin or after they end, as I can focus on tasks rather than replying to emails/calls and other inquiries from my customers.  

IN THE HOME: Share with us one of the ways in which you enjoy spending time with your daughter.  Playing games whether it is board games or card games.  It provides both a venue for conversation as well as a challenge for the mind.  Our new favorite game is "Sequence", strongly recommend it.  


Mixing Kitchen, Office and Home together- share one belief or truth that has enabled you to really live out your best One Life.  Live in the moment; don't worry about what happened in the past nor concern yourself with what may happen in the future.  Be present today for today's sake. 

MEET STEVE:  Steve lives in Barrington and is a single parent to his seven-year-old daughter, Savannah.  Professionally, Steve is a director of finance for the 10th largest not-for-profit health care system in the United States.  In his free time, Steve is on the Barrington 220 Board of Education, Co-Leader for Girl Scout Troop 310, a Room Parent at Countryside Elementary School, on the Notre Dame Club of Lake County Board of Directors and volunteers for a variety of causes.  


"PERFECT" Manhattan


It’s truly perfect!

Ken Kuhn enjoys spending some of his free time serving up drinks here at One Life Kitchen. Ken is married to Carol and they have two adult children - Steve and Rachel.

Chef Sean's Favorite Summer Meal

Rosticciana - Tuscan Grilled Ribs



Chef Sean McGuire learned this recipe three years ago while traveling in Italy. It's one of his favorite summer meals to make. Pair it with a ceasar salad and a slightly chilled glass of wine. 

ABOUT CHEF SEAN MCGUIRE: Sean spent many years cooking in San Francisco and California wine country. Sean is a chef and teaching instructor at One Life Kitchen and serves as a private chef in the Barrington area. Sean is married to Shauna and they have two little boys.

Your Next New Wine Obsession

First it was big and bold, then unoaked Chardonnay and natural wines, now rosé prosecco. Some winemakers in Italy have been producing this wine for some time now, releasing it as generic IGT – Indicazione Geografica Tipica – wines, but 2021 will be the year of prosecco rosé as Italy has now created a legal designation for this beautiful pink bubbly and it will officially hit the market New Year’s Day 2021! Rosé aperol spritz, anyone?

This prosecco rosé will be a blend of Pinot Nero (Pinot Noir) and Glera – the native grape responsible for the wonderful Italian bubbly wine we all know and love. These wines will be dry or off-dry and vintage-dated, with all of the floral aromas that define prosecco.

While we wait for these exciting new wines to be released, let’s celebrate with some of our other favorite sparkling rosés! As we dive into Champagne we see rolling hills of Chardonnay, Pinot Noir, Meunier, and a few other varieties growing with old châteaux storing hundreds of years of history and preparing many wines for release. From here I recommend picking up a bottle of Billecart Salmon Brut Rosé for a night you want a real treat.

Franciacorta may be very familiar to those Italian wine-lovers, yet still unknown to many. Here we see winemakers producing high quality sparkling wines in the way of Champagne, what we call the méthode champenoise, creating those tiny, uniform bubbles that hit the palate just right. With extended lees aging these wines are complex, with toasted nut and brioche flavors on the palate! You can never go wrong with a Franciacorta and I recommend Ricci Curbastro Franciacorta Brut Rosé.

There’s so many amazing sparkling wines out there, but I cannot end this without mentioning Australia! Australian winemakers have worked so hard to make a name for themselves. The country has been known for mass-produced, cheap wines, but there are many incredible producers all around the country today and the one I’d like to highlight is Lambert Estate in Barossa. I came across this producer as I was browsing the grocery store looking for an affordable wine to enjoy that night after I heard the wonderful words from my husband, “I’m making dinner tonight, go out and get a bottle of wine you’d enjoy”, music to my ears! I saw this bottle sitting there and thought, “huh, I’ve never had a sparkling wine from Barossa, I may as well try it” and boy was I happy that night – as soon as that cork was out the room was filled with strawberry, brioche, almond, and cherry aroma-galore!

Keep enjoying and trying new wines and as we anticipate the release of prosecco rosé be sure to check out the One Life Wine Club – December will feature sparkling wines from around the world!


- Miranda