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Chicago Explored

I'm back from an incredible press trip to Chicago with Choose Chicago--one of the best big cities on earth. In fact, Chicago was just voted the Best Big City in the United States for the seventh years in a row, and I have to say... I agree.
When visiting Chicago, there is so much to see and do--and the city caters to every type of tourist, whether you're into sports, (from the Chicago Bulls tot he Bears to the Cubs--they've got it all!) sightseeing, shopping, dining, or just taking in the stunning and historic architecture. From the award winning food scene, beautiful parks and green spaces, luxury hotels, attractions, and vibrant neighbourhoods, it's a city everyone should add to their travel bucket list. 

Here's a rundown of where I stayed, where I dined, and what I visited, to help you plan your itinerary for your upcoming Chicago trip! 

How to get there

We flew out of Ottawa with Porter, and landed in Toronto's downtown Billy Bishop airport. Flying Porter is always an excellent experience--from the service they provide to every customer, to the complimentary food, snacks, and beverages (including wine and beer...hello!) on board. The lounge is spacious, with comfortable seats, tables, and chairs, with places to eat and shop--and the security check-in is a breeze. From Billy Bishop airport we got on a plane to Chicago, and the flight was under two hours. Another great reason to fly to Chicago--it's such a short flight! (And Porter makes the entire experience extremely comfortable and stress-free).

Where to stay

This Chicago trip with Choose Chicago had me staying in the beautiful and luxurious Gold Coast neighbourhood--at the legendary Viceroy Hotel. The Viceroy is set on the site of a 120-year old landmark building, and is one of the finest hotels in Chicago near Magnificent Mile, surrounded by high end boutiques and Michelin star restaurants in the Gold Coast.  

Bonus: The hotel's Somerset restaurant serves up delicious breakfast and dinner, (indoors in their 1920's themed seating area) or outside on their beautiful patio. The hotel is also home to the Devereaux, the 18th floor rooftop lounge (and where you'll find the hotel's outdoor pool). The views of the city's skyscrapers and Lake Michigan are simply breathtaking from the 18th floor! The hotel is perfect for a girls trip or a couples trip, and they also cater to families--they have great activities and events in store for fall and the upcoming holiday season. 

Our room was beautiful--spacious, modern, comfortable, with floor to ceiling windows and Lake Michigan views. The service was excellent; everyone knew our names, and everyone we met was friendly and helpful. I would absolutely recommend Viceroy Hotel to anyone asking me where to stay when they travel to Chicago. 

Where to dine

Where to dine in Chicago? Considering it's one the most awarded and recognized culinary cities in the United States and worldwide, this is not an easy task and one that could take days to figure out, because there are countless excellent restaurants. Lucky for me, all the restaurants I dined at were selected by Choose Chicago and all of them were outstanding. Let's break it down. 


We had dinner at Adalina on our first night, just a couple of blocks from our hotel. The restaurant was an entire vibe! It was busy, the decor was stunning, and we were seated right in the middle of all the action. We enjoyed the four cheese garlic bread table service, the Mafaldine pasta dish (a delicious cacio e pepe!), short ribs with gnocchi alla Romana, and for dessert, we tried the Cookie Plate and Adalina Tiramisu. Everything was delicious, and I highly recommend this restaurant for your visit to Chicago. 

Girl and the Goat

Dinner at Girl and the Goat was a culinary experience! Top Chef Stephanie Izard's restaurant, located on Restaurant Row in the West Loop, is always busy and buzzing--and there's no wonder why! The food is incredible, with a focus on global cuisine featuring local ingredients. Most plates are meant to be shared, and we enjoyed the olive garlic focaccia, their famous green beans dish, (truly delicious!) chickpea fritters, grilled chicken skewers, and lamb perogies. We ended the night with the blueberry shortcake and brown butter cashew tart. So good! 


LUXBAR is located in the Gold Coast neighbourhood, practically across the street from Viceroy Hotel, right in the centre of all the designer shops. It's considered the quintessential American bar and eatery, and the menu serves all your favourites--sliders and fries, chips and guacamole, and pizza. I've enjoyed deep-dish classic Chicago style pizza before, but the pizza at LUXBAR is actually Detroit style--and it was so, so good! The food and drinks are excellent, but even more fun is the people watching--it's packed full of stylish people stopping by for a quick bite to watch the game, or take a break from shopping. 

The Evie

The Evie is located right in the heart of it all on Michigan Avenue on the Magnificent Mile, led by a team of lifelong Chicago restaurant figures. This locally owned upscale dining destination serves a great mix of classic favourites like steak, sushi, burgers and fries, freshly baked breads, and Chicago-style hot dogs. The service was excellent, and everything we ordered from the menu was delicious. I loved the awesome views of Michigan Avenue from the large windows of the second floor restaurant. (The dessert menu is also amazing!). 

Avli on the Park 

I consider myself a food expert when it comes to Greek food and if you're looking for a highly rated authentic Greek restaurant, you have to try Avli on the Park in downtown Chicago's Lakeshore East. The restaurant is stunning and extremely spacious, with white walls, floor to ceiling windows, fishing ropes hung from the ceiling, and a sleek and modern design that makes you feel like you're dining on a Greek island. The food is as authentic as it gets (the Chef is Greek) and the spreads, salads, and main dishes (think classic Greek food, from chicken souvlaki, Greek salad, tzatziki, and potatoes) were perfection. 

Okay, believe it or not, there is more to do in Chicago than just eat, though that's a big part of every visit! What else should you do in Chicago? 

Here are some ideas:

Skydeck Experience

If you've never been to Chicago before, you have to visit Willis Tower--the tallest building in Chicago and the third-tallest building in the Western Hemisphere. The view from the top of the 103rd floor (yeah, it's really high up!) offers incredible views of the city, and you can also see up to four states. If you're brave enough, step out on to The Ledge, a glass balcony extending four feet outside Willis Tower. The best way to start your experience is by going through the interactive museum on the main floor, before you head on up. This will give you excellent insight into what makes Chicago so great, and you'll learn about the city's awesome history and what makes it so great today. 

Museum of Ice Cream

This one is fun--and sort of involves food--the ice cream kind! This interactive ice cream museum is Chicago's largest playground filled with unlimited ice cream and fun activations, like a large sprinkle pool you can jump in, games, (the kinds you play at a fair) mini golf, and more. And yes... there is lots of free ice cream. 

Art Institute of Chicago 

I always love visiting the Art Institute of Chicago--it's a stunning building in Grant Park, founded in 1879--one of the oldest and largest art museums in the United States. The museum features nearly 300,000 works of art and over 30 special exhibitions yearly. 

AIRE Ancient Baths

We were lucky enough to start one of our mornings early so we could have the entire AIRE Chicago space to ourselves to shoot some content before the doors opened to everyone else--and it was blissful! AIRE Chicago is located in a restored factory from 1902. The entire experience is a journey of relaxation in a candle-lit space, full of thermal baths at different temperatures from hot to cold, a bath of a thousand jets, a salt water bath, and indoor/outdoor pool with waterfalls, and aromatherapy rooms. We finished our ancient baths experience with an incredible 30 minute full body massage. The perfect way to star a very busy day! This activity is fun for couples or girlfriends travelling together. 

Starbucks Reserve Roastery 

Did you know the largest Starbucks in the world is in Chicago? The Starbucks Reserve Roastery on the Magnificent Mile on Michigan Avenue is just amazing--35,000 square feet, five stories, even a curved escalator (so cool!). You can shop the store (mugs, accessories, tumblers, and so much more!) and enjoy their FIVE floors of coffee, cocktails, and food. The fifth floor is a cocktail bar, (serving up all your classic faves) and you can even indulge in some Italian food, at the Italian style sandwich shop. Coffee? Of course! Every kind you can image, and specialty coffees you won't find at any other Starbucks. 

Maria Pinto Boutique

As part of my press trip I had the chance to experience a personal shopping day in Chicago's Gold Coast neighbourhood in designer Mario Pinto's boutique. Maria Pinto is one of the city's most recognized fashion designers, having styled celebrities like Michelle Obama!  Her store is beautifully designed and the service is amazing--everyone was so helpful, and it felt great to try on her many designs and clothes. I left with a stunning leopard print dress that I've already worn several times back home--it's practical, stylish, comfortable, and will last for years. It truly is effortless style and the quality of designs speak for themselves. Her clothes and the materials she uses are made so you can go from the office to after work drinks, and still feel and look amazing. Personalized shopping is the best, and I loved this experience. 

Second City 

Second City is an institution of humour, and where many famous comedians got their start, like Canada's own Catherine O'Hara, Eugene Levy, Mike Myers, Dan Akroyd, and John Belushi, Tina Fey, Amy Poehler, Steve Carell, Bill Murray and Chris Farley... to name a few! We caught the show The Best of The Second City: Chicago Style, where the comedians performed some hilarious sketch comedy and improv, of course. We laughed for hours and it was such a highlight of our trip. My sister said she wanted to spend every single night at Second City, it was such a blast. 

Three Dots and a Dash
After our laugh out loud experience at Second City, we headed to Chicago's famed tiki cocktail bar, Three Dots and a Dash. It's a little tricky to find but no worries--it's next to a big firehouse so we chatted with some fire fighters to ask how to get to .... "Three Dots and a Dash? Everyone asks us--just turn left here." They were so kind and helpful and the drinks at the bar were delicious and the perfect way to end our evening. 

Chicago--I miss you so much already and I can't wait to visit again! Choose Chicago--thank you for the most incredible few days in the Windy City. It was literally perfection and I am proud to say I'm Chicago's number one fan girl.