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City Guide: Traveling High in Chicago

Sailun Tires

For many North American travellers, America’s largest cities have a pecking order – New York, Los Angeles, Las Vegas, and San Francisco often get visited first. We’re attracted to the landmarks, the nostalgia of having a photo where our favourite movies and television shows were filmed, and promise that everything you love to do at home is happening there except WAY BETTER. But where do you go when you are more interested in a truly authentic experience? Chicago.

Home to 2.7 million people, Chicago is America’s 3rd largest city and was recently named #1 Best Big City in the U.S. by Condé Nast Traveler’s 2017 Reader’s Choice awards. Roughly located in the middle of the country, it’s easily accessible from most Canadian cities in one flight, making it easy to get to for a guys’ trip, family vacation, or for your next bucket-list sporting event or concert. If you’re looking for it, you’ll find it, and if you find yourself lost, a friendly Chicagoan will be happy to help. So proud of their town, they will also likely direct you to their favourite local hangout along the way.

Like Canadian cities, Chicago comes alive in the summer with festivals, events, and outdoor activities. Although landlocked, Lake Michigan provides all the feels of a coastal city with vibrant beaches, boating and one one of the city’s most important landmarks – Navy Pier. It’s also nearly entirely flat, so walking the parks, river path, or exploring one of the neighbourhoods is easy – and with wider sidewalks and fewer crowds than Big Brother New York, you’ve got more personal space too.


Where to Stay?

The Viceroy in Chicago - Chicago City Guide | SWAGGER Magazine
Photo: Courtesy of The Viceroy in Chicago

The Viceroy – 1118 N State Street

Located in The Gold Coast strict, the Viceroy is for those who want the high style that chain is known for. Designed by noted architects Goettsch Partners and hospitality design firm TAL Studio, the exterior of the building is a study in contrasts. The preserved 4-story brick and terracotta façade of the original cedar hotel is juxtaposed with a new 18-story glass tower that now houses all the of the hotel rooms. The aesthetic for the interiors is a mix of midcentury and art deco that are rooted in Chicago’s architectural history. With luxe details in marble, brass and rich wood tones the hotel feels updated, modern and very chic. Each room is fashioned with a gorgeous cubist wall mural inspired by the artist Meitte Brave that creates a distinct headboard feature wall. The Viceroy Chicago has 180 guest rooms and a rooftop pool on the 18th floor to take a dip, take in the views, and enjoy a cocktail or small plate from the adjacent Devereaux rooftop bar (which gets lit in the evening!).

Guest Room at The Vicroy hotel in Chicago (Photo: Courtesy of The Vicroy hotel) | SWAGGER Magazine
Guest Room at The Vicroy hotel in Chicago (Photo: Courtesy of The Vicroy hotel)


The Blackstone, Autograph Collection – 636 S Michigan Avenue

This landmark hotel is located on The Cultural Mile. It’s a throwback to the city’s legendary past, celebrating its history and culture but not overlooking the small details that make a hotel stay comfortable. Rooted in history, this hotel opened its doors in 1910 and has been visited by the likes of Eisenhower, Truman and Kennedy. The hotel was then revitalized in 2017 and converted to The Blackstone, Autograph Collection. The hotel now boasts a glorious collection of local art through out the lobby, gallery and the common spaces. The hotel’s connection to the art community in Chicago is quite strong and they strive to be a cultural destination in the city. The lobby is an eclectic mix of whimsical art and furniture mixed in with the traditional aspects of the old hotel. Paying very close attention to the buildings heritage and restoring it with all of the woodwork, plaster work, and mouldings you can still feel the rich history of the hotel even though it has been updated. Overlooking the shores of Lake Michigan, Blackstone suites have incredible views Grant Park, Buckingham fountain, and Boeing gallery.

Hallway at The Blackstone, Autograph Collection hotel in Chicago (Photo: Courtesy of the The Blackstone hotel) - Chicago City Guide | SWAGGER Magazine
Hallway at The Blackstone, Autograph Collection hotel in Chicago (Photo: Courtesy of the The Blackstone hotel)


Hotel Robey – 1616 N Milwaukee Ave.

If an Art Deco, boutique hotel is your style, stay at Hotel Robey in Wicker Park. The L train runs behind the hotel so getting around ‘The Windy City’ from The Robey is a breeze. One of the most recognizable landmarks in this neighborhood, the building was originally zoned an office. With its unique triangular footprint, no corner has been un- touched in this gorgeous rejuvenation. The lobby and common spaces have a relaxed and casual feel to them with a mix of modern and vintage appeal. The designers have taken the original art deco interiors and played them up with a gentleman’s lounge feel. Herringbone floors, terrazzo, rich leathers, and a moody colour palette of greens, deep reds and blues make this a hotel a stand out when it comes to design. Tucked away from the main tourist areas of Chicago, The Robey stands high above the intersections of Damen, Milwaukee, and North Avenues and is the only skyscraper for miles, so the rooftop pool and the Cabana Club Bar make for perfect vantage points. On the main floor is the delightful Café Robey, perfect as a first stop before heading out for the day or lunch on a hearty tuna melt or Cuban sandwich.

Panorama Suite at the Hotel Robey in Chicago (Photo: Courtesy of the Hotel Robey) - City Guide | SWAGGER Magazine
Panorama Suite at the Hotel Robey in Chicago (Photo: Courtesy of the Hotel Robey)


Where to Eat & Drink?

Chicago is for eaters! Leave your diet at O’Hare and accept that you may go home a little softer around the middle than when you arrived. When you think Chicago, everyone immediately thinks of Chi-town pizza. We’ve curated a more diverse selection of what they have to offer — that you may never have thought of.

Shrimp and Grits from Big Jones Chicago - City Guide | SWAGGER Magazine
Shrimp and Grits from Big Jones Chicago (Photo: Courtesy of Big Jones)


Big Jones

Start your day with a fill of grits and beignets in the heart of Andersonville. Big Jones uses Southern heirloom cooking techniques with a focus on sustainability. Cozy, flavourful and filling, you are guaranteed to leave with a full belly and fuel the day’s 10,000 steps. Try to snag a table at the front of the restaurant and enjoy the people watching.



Located inside the Viceroy, Somerset is part of one of Chicago’s most notable restaurant groups – Boka. The two-storey 1920s-inspired design is reminiscent of country club culture, serving seasonal American cuisine. Sophisticated and stylish, the menu includes everything you really want to eat after a busy day – oysters, Spanish octopus, steak and seafood, and the not to be missed tagliatelle in a mushroom bolognese. Start at one of the two bars and enjoy a craft cocktail from their expertly curated drink menu or simply let one of the passionate barkeeps know what you’re thirsty for.



In Chicago’s West Loop is the decadent, 1950s-inspired BLVD. Think old Hollywood meets Chicago steak house, and keep your eyes open for your favourite celebrity (does Oprah still hang out in Chicago?). From the outside you may think you’re at a night club (which it once was) but once inside you’ll see the grand staircase and sparkling chandeliers overlooking the vibrant lounge scene. The dining room is filled with large booths plenty big enough for you and your friends to enjoy a 32oz steak or seafood tower. Better yet, splurge and explore the caviar service and all of the decadent side dishes.


Mango Pickle

Chicago is known for it’s deep dish and steaks but when you’re ready for an ethnic flavour bomb, head over to Mango Pickle on N Broadway Street. Chef-owner Marisa Paolillo is a Chicago native who spent 10 years living in Mumbai and exploring the flavours of Western India. She brought back the culinary traditions of South Asia and put a modern, Mid-West spin on it, opening Mango Pickle in 2016. Start with the seasonal veg samosas and don’t miss paneer pops, butter chicken and locally-raised lamb daily special.


Velvet Taco

After a night out at the rooftop bars, get a step ahead of your hangover at Velvet Taco. Open late, post-party people line up for any of their over 20 different varieties of tacos, crisp ‘tots’ and ‘Elote’ corn. It’s busy, and worth the wait. Be sure make a friend or two while waiting, the crowd is there to have a good time. The menu is long so it will take a few minutes to choose what to order but there are no wrong decisions to be made here.


Devereaux – 18th Floor at the Viceroy (1112 N State Street)

Although you access Devereaux via the alley to the left of the hotel, this rooftop has all the art deco elegance and charm that the Viceroy hotel is known for. Enjoy the view poolside or from through the floor to ceiling windows, while you snack on small plates from the hotel’s award-winning restaurant Somerset.


Cindy’s Rooftop – 13th Floor at the Chicago Athletic Association (12 S Michigan Avenue)

This bustling open-air terrace has panoramic views of Millennium Park and Lake Michigan. Open for brunch, lunch, dinner, or a cocktail and a selfie. The cocktail menu is extensive and includes an ‘apothecary service’ with large format cocktails like old fashioneds, negronis, or the 3 litre Jolie Folle Rose (recommended to serve 10 – 20).

Stay tuned for our upcoming round up of Chicago’s hottest rooftop bars.


What to Do?

Sunset view in Chicago (Photo: Courtesy of - City Guide | SWAGGER Magazine
Sunset view in Chicago (Photo: Courtesy of


Architecture River Cruise with Chicago’s First Lady

A great way to orient yourself to the layout and magic of Chicago, the Architecture River Cruise is a must-do. More than a float through the city, the volunteers from the Chicago Architecture Foundation (be sure you choose this and not a knock-off tour) share their expert knowledge of the history and development of this great American city. More than a guide, their docents are an elite group of content experts, hand-selected and carefully trained to serve as the face of the organization. It’s clear that volunteering on the First Lady is a position of honour! The best 90-minutes you’ll spend in Chicago.


Explore Wicker Park / Bucktown

Located outside downtown Chicago, think of Wicker Park (also known as Bucktown) as what Brooklyn is to Manhattan. Shop the vintage and flagship stores, explore galleries, theatres and some of the city’s most innovative restaurants, clubs and bars. Be sure to walk The 606, Chicago’s newest green space. Formerly the Bloomingdale Line, the trains have been replaced with 4.3 km of elevated public park, track and art space.


Be Physical

Run along the shores of Lake Michigan, jump into a beach volleyball game, or take in one of the many yoga classes in the park, at the ‘get fit at the zoo’, or even from the 94th floor observation deck at 360 Sky Yoga.



AIRE Ancient Baths (800 W Superior Street) – Modeled in the spirit of traditional Roman, Greek and Ottoman ancient baths, an experience at AIRE provides you with the ultimate moment of self-care on your holiday. Located in a restored 1902 factory, explore each of the six thermal baths (hot bath, ice and cold plunges, warm pool and the flotarium – as salty as the Dead Sea). Massage packages are also available, along with the ultimate Wine Experience where you bathe in Spanish Tempranillo grapes while you enjoy a cranio-facial massage in a private area.


Where to Shop?

If you want it you’ll find it, so prepare your credit cards.

The Magnificent Mile in Chicago (Photo: Courtesy of - City Guide | SWAGGER Magazine
The Magnificent Mile in Chicago (Photo: Courtesy of

The Magnificent Mile boasts over 460 retailers ranging from big name department stores and luxury brands to luxe fashion outlets. Located on Michigan Avenue, this area stretches between Lake Shore Drive and the Chicago River. Be sure to check out the iconic Saks Fifth Avenue, Neiman Marcus and Macy’s.

Wicker Park – great window shopping, pub-hopping, vintage and beyond, explore W North, N Milwaukee, and N Damen Avenues. Notably, visit the Adidas Originals Flagship Store to shop limited edition styles and Vintage Underground for clothing, accessories and other treasure.

Build a customized bag in Lincoln Park at Laudi Vidni (1007 West Armitage Avenue). “Individual” spelled backwards, Laudi Vidni gives shoppers the opportunity to create customized leather goods including bags, wallets, belt bags, passport holders and more. You choose your leather from the swatch wall, lining and hardware, and have it shipped in 3-5 weeks. Can’t wait? Fear not, they have a huge selection ready to wrap up on the spot.


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