It’s been quite a few years since I was in Chicago and yet it felt like just yesterday I was taking my photo in front of the Big Bean (actually called Cloud Gate by Sir Anish Kapoor and meant to reflect clouds). So much had changed in eight years and yet, somehow, it felt like I was home. If you haven’t taken the family to this incredible city, here’s why you should plan a trip for this coming holiday season.

Stay In Style

Named after John Kinzie, the renowned Chicago settler and silversmith, the Kinzie hotel offers style with a homey feel. This boutique hotel is centrally located near Michigan Avenue and the loop, and features spacious rooms and suites, with lots of windows, incredible views, modern décor, Netflix, pet-friendly stays, and giant comfy beds.

Two added touches that make the Kinzie Hotel an unforgettable place to stay is their continental breakfast is served fresh every morning on a beautiful credenza by the elevators on each floor. The idea is to throw on your robe and grab a healthy and delicious start to your day.

The other unusual feature is the tokens you receive upon check-in that you can use towards cocktails during Happy Hour at the Double Cross Lounge. Here you’ll enjoy a relaxing atmosphere with fresh tapas style food items to accompany your experience. It’s a chance to throw on some Netflix for the kids and let the adults escape for a while.

Chicago - Kinzie - Photo Sabrina Pirillo

Get cosy in style at Kinzie – Photo Sabrina Pirillo

C is for Culinary-Masterpiece

Ranging from deli sandwiches to dim sum to flavours from around the world, Chicago is one of the leading culinary cities offering bursting flavours for every appetite.

BEATNIK is your non-traditional restaurant and cocktail bar featuring foods from all over the world and sure to satisfy any palate. The décor and ambience give off a bohemian and exotic vibe surrounded by lush interiors and elegance surrounded by a cosy feel. Menu items are shareable, and the entrees make it feel like you’re dining in any part of the world.  On this eclectic menu, you’ll find Curry Meatballs, Roasted Lebanese Style Lamb, and charred broccolini.

Latinicity’s newest addition, Pueblo, a Latin American Cooking Class, is a fabulous way to spend time with family and friends, especially on a rainy day. The cooking class showcases home-style cooking with a Latin inspiration. You’ll make all kinds of yummy foods such as fresh guacamole, Caldo de Hongos (mushroom soup), and my personal favourite, the Cucumber Margarita, where serrano peppers are sliced open and sit in a bottle of tequila for two days. Then, mixed with a cucumber puree and rimmed with Tajin (chilli peppers, lime and salt mix), the only thing that would make it better is if you were sipping it on a beach! Ole!

Chicago - Latinicity Guacamole - Photo Sabrina Pirillo

The author shows off Guac making skills from Latinicity – Photo Sabrina Pirillo

Located a few minutes away from the Kinzie Hotel (again, this is where Netflix comes in handy), Tortoise Supper Club is an upscale restaurant featuring a grand piano and live jazz Friday-Sunday. Tortoise creates a warm feeling with sharable apps including the Seafood Lazy Susan, delicious skirt steak and liquid desserts, like the Brandy Alexander with homemade ice-cream.

Expanded into a bi-level café and bakery from its original 10 x 10 marketplace location, Executive Pastry Chef Sandra Holl took her rustic French pastries to a whole new level and created Floriole. The baked goods are fresh and delicious like their Ham & Cheese Croissant, lavender pound cake, quiche, ricotta toast and the list goes on. Savoury & sweet heaven on earth!

Imperial Lamian needs to be a stop on your food tour. I’m salivating about going back as I type this. Offering authentic and refined Chinese cuisine in a beautiful and inviting setting, you’ll never want to leave from the moment you walk in the elegant foyer featuring unique birdcage pendant lights to the minute dessert is served. Known for their Lamian noodles and dim sum, you’ll have a view of the open kitchen watching noodles made from scratch. The one menu item you must have (I promise you won’t be disappointed) is the Xiao Long Bao; broth filled scrumptiousness filled with either Shanghai (pork), Szechuan (spicy) or duck. Imperial Lamian makes it easy to spend hours just enjoying life the way it was meant to be, with delicious food in a fabulous setting surrounded by good company.

Too busy exploring the Windy City? Stop in for a quick bite at Potbelly Sandwich Shop. And you don’t even have to wait in line, place your order online for in-store pick up. You’ll find everything from tasty sandwiches to salads, soups, homemade cookies and of course, shakes, malts and smoothies (oh my!). You’ll also love the entertainment from the staff so even if you do decide to stand in line, you’re in for quite the show.

If you’re more of the ‘I want to try a bit of everything’ traveller, then give Second City Chicago Food Planet a go as they’ll take you around famous Chicago neighbourhoods while sampling different cuisine’s including Middle Eastern, olive oils, teas, fudge, French pastries and of course, deep-dish pizza.

Play Time in The Windy City

The American Writers Museum is not just for aspiring writers. It encourages its visitors to celebrate American writers and their influence on America’s history incorporated into daily life. You’ll find all kinds of fascinating works including innovative and interactive exhibits for kids and adults alike, a word waterfall consisting of American writer quotes merged into one giant exhibition highlighting each writer throughout the installation.

I challenge you not to be inspired when you leave.

The Art Institute of Chicago is the 2nd largest art institute in America, built in 1892 for the World’s Fair. The Museum houses 20 different collections of art including the Modern Wing featuring Andy Warhol’s collection, Medieval and Renaissance, Contemporary, Chicago Architecture and the list goes on. It’s also home to a magnificent collection of Impressionist paintings outside of Paris, which include the works by Monet, Renoir, and Van Gogh.

The original home of The Second City will leave you in stitches. With the mainstage show always changing, you’ll never see the same show twice. Be sure to grab a bite beforehand or a post-nightcap at 1959 Kitchen & Bar.

Holiday Traditions:

It’s never too early to start thinking about your holiday plans. And, if the holidays bring up memories of stressful shopping, wish lists that seem a mile long and that one uncle who you can never find the right gift for, then visiting Chicago will bring you back to the real meaning of the traditional holiday.

Chicago holiday traditions have a rich and long history and wouldn’t be complete without grabbing a glass of wine at the Walnut Room and admiring the giant Macy’s Christmas tree. Once you’re all warmed up, head outside and see the eight window holiday displays, which change themes each year.

Macys Christmas Tree - Photo Sabrina Pirillo

Macys Christmas Tree – Photo Sabrina Pirillo

Magnificent Mile Lights Festival Tree Lighting Parade stretches along Michigan Ave turning it into a Winter Wonderland! On the Saturday before each Thanksgiving weekend, you can catch the parade and firework show over the Chicago River.

Christkindlmarket Chicago brings a taste of Germany, Europe and local traditions in the beautiful outdoor setting of Daley Plaza. Grab a cup of warm spiced wine (or hot chocolate for those underaged) as you shop for unique and traditional holiday gifts.

Chicago - Christmas Market - Photo Sabrina Pirillo

Christmas Market – Photo Sabrina Pirillo

Of course, one cannot go without seeing the stunning and magnificent tree lighting at the epicentre of Chicago, Millennium Park.

For someone who hadn’t been skating in seventeen years, ice-skating at Maggie Daley Park was a treat. With a beautiful skating ribbon design, you’ll feel like you’re gliding and winding creating a feeling of freedom, with the stunning city skyline as a backdrop.

Chicago - Skating - Photo Sabrina Pirillo

Photo Sabrina Pirillo