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Gentleman's Travel Guide: Chicago

In our first edition of the Gentleman’s Travel Guide, our readers were taken on a guided tour of the need-to-know when visiting San Francisco.

With our second edition, we focus on Chicago, Illinois.  The Midwestern city is best known by two popular monikers “Chi-Town” and “The Windy City." It is also famously known as the birthplace House music. 

So, repare to be guided through what you’ll want to see, touch, taste and hear in Chicago.


The Tremont Chicago:  While hotel location is essential to a visitor, and a good price is as well, look no further than the Tremont. The Tremont boasts 135 charming rooms with grand amenities like marble bathrooms grand furnishing that gives a classic modern spin. The hotel located on 100 East Chestnut, is right in the heart of Chicago’s downtown splendors. Close to the magnificent mile and Rush Street, the second you step outside the hotel fine shopping and dining possibilities are nearly endless at the most affordable price.

The Palmer House Hilton: The Palmer House Hilton Hotel located in Chicago’s South Loop area gives a grand and historic feel from the second you enter the lobby to the second you check out. The hotel has a contemporary design modeled after 140 years of Chicago history and is a registered member of Historic Hotels of America. The hotel isn’t only luxurious, but fairly priced, and close to Chicago’s millennium and grant parks.

The Trump Tower:  Being the second tallest building in Chicago’s vast skyline, and named after the Donald himself, you can expect a royal treatment without completely breaking the bank. Featuring 339 guestrooms/suites with detailed amenities and signature Trump service, the hotel also boasts a 23,000 square foot spa and a signature elegant American-cuisine restaurant, the Trump Tower serves as a premier place to stay that goes beyond a room to just drop your bags and rest your head for a moderate price. 

The Waldorf Astoria: The Waldorf Astoria was “Ranked the #1 Hotel in 2011 by Conde Nast Traveler” for a good reason. This luxury hotel is strictly for big spenders with each room modernly designed and equipped with many different room accommodations to fit your needs from luxury rooms, to lavish fireplaces and grand balconies. Located in the heart of Chicago’s Gold Coast, The Waldorf is steps away from Chicago’s finest 5-star shopping and dining selections.


Tavern on Rush: Venture over to the Gold Coast’s for some of Chicago’s finest American contemporary featuring prime aged steak and fresh seafood with premier outdoor and multilevel seating overlooking Rush street.  

Schwaa: How is one of Chicago’s most curious and praised 9 course cuisines enjoyed if you cant even find the front door without discovering it? Welcome to Schwaa, located in Wicker Park. Aside from the secrecy and reservation and BYOB only alcohol options, Schwaa makes up for with wild and unforgettable dishes from head chef Michael Carlson. Refer to their site and/or Yelp reviews to understand the complete experience. 

Moto: The world-renowned Moto restaurant is complete culinary voyage. Artistic and futuristic barely sum it up as the food is prepared more scientifically. Using liquid nitrogen and Class IV lasers to prepare ingredients from all around the world, at Moto you can ‘expect the unexpected’ but chances are your taste buds are going to tingle from the eclectic multi-course menu. Again, refer to their site or Yelp reviews for more detailed info.

Sikia: Enjoy one of Chicago’s finest ethnic foods without getting stuck in hefty downtown traffic. Sikia, located in the south side neighborhood of Englewood, this African-inspired restaurant expands to tastes from Brazil, Jamaica, and New Orleans with an unforgettable twist on Sunday brunch.

Coco Chicago: This fine Puerto Rican eatery located in Humboldt Park captivates the taste and look of the Caribbean. With custom artwork, exposed brick, and windows that open during the summer to turn into the restaurant into a sidewalk café, the authentic food isn’t the only thing that helps bring Puerto Rico to Chicago. Did I mention all the homemade rums?


Quimby’s: Quimby’s labels themselves as ‘specialists’ in selling unusual publications, aberrant periodicals, comic booklets, and independent zines. For the reader looking for a one of a kind experience, look no further than Quimby’s.  

Myopic Books: While many signs point to no (no bathroom, no cell phones, no photography, no exchanges) the book selection all points to yes. One of Chicago’s largest used bookstores; Myopic has three floors of books with over 80,000 editions in fiction, art, architecture, music, film and etc.


Michigan Avenue’s ‘Magnificent Mile

If you need some quality threads from quality names, Michigan Avenue’s ‘Magnificent Mile’ area is really the only place you need to be. Moderately priced retailers are also readily available with multilevel floors you wouldn’t find in most cities.

Mall: The Water Tower Plaza is really the only mall in the City of Chicago and the only one you’ll need to know. The 7 level building is right in the heart of the Mag Mile, and boasts over 100 stores including a massive Macy’s and their unforgettable food court with near endless options, food-life.

Department Stores: The Macy’s at the Water Tower Plaza is as many floors as the plaza itself. Right down the street sits Neiman Marcus, Barney’s New York, and Saks Fifth Avenue. For the man on a budget and looking for a steal, Nordstrom Rack nearby boasts designer names at bargain prices.

Specialty Retailers/Boutiques

Polo Ralph Lauren: Sure, Ralph Lauren can be found at nearly any department store you go, however Michigan Avenue’s location doesn’t only happen to boast 4 stocked floors of every Ralph label, but it’s also the world’s largest Polo store. Looking like a mansion from the outside, and featuring it’s own restaurant next door, if you like Ralph Lauren, welcome home.

Giorgio Armani Boutique: This sleek boutique features top notch modern design with personalized service that lives up to the Armani name.

Marc by Marc Jacobs: Located in Wicker Park, the Marc Jacobs store has the perfect mix between a designer look, without the full designer price.

Topshop: Only the second location in the US, (NY being first) the European phenomenon Topshop found its place in Chicago after the Michigan Avenue location Border’s superstore went under. While the store looks like a sleeker H&M, the jackets/blazers and accessories are red carpet worthy.

Accessories: For the top shoe, look no further than the top brand. You know the one with the swoosh. Niketown isn’t only a great place to get a good pair of sneakers for the moderate spender, but while the store is broken into sections like golf, basketball, running, and soccer- you may find reason to pick up more than just one pair. 

Now when it is time for a shoe that dresses up your day or night, visit Fluevog Shoes.  The retailer carries a wide variety of styles to suit your needs.   

Toiletries: To get to the skin of the matter, Kiehl’s a variety of men’s grooming products to assist gentlemen in looking their best and being there at all times.


Excalibur: being one of the largest nightclubs in the city with over 60,000 feet of partying featuring multiple levels of different dance music suited to your mood.

The Paris Club: While the entrance serves as an elite place to grab drinks and snack on French foods, the upstairs is a whole different story. Modeled after the high-energy clubs in Europe, its no surprise Paris Club attracts celebrities and high rollers from all over the globe. Featuring a 25-foot bar and a retractable roof for outdoor enjoyment, the Paris Club is worth the wait. That is if you can get in.

Vision Nightclub: Vision has been voted as the #1 Mega Club in America by the indie publication URB Magazine and also received accolades from DJ Mag as one of the top 100 clubs in the world.  The club features a diverse array of music choices for over 2000 clubbers a week.  It also sits as the crème de la crème of clubs in Chicago’s nightclub scene.


If there’s one thing visually appealing to the eye, it’s ‘The Bean’ located in Millennium Park. And while your there, the Millennium Park Orchestra is an architectural feast for the eyes – even if nobody is playing at the time. Steps away are the renowned Art Institute Museum featuring numerous famous painting acquisitions that you must see for yourself.

For two great views and different experiences, nearby all the fine dining and shopping, take a break and go up 1500 feet into the skyline at the Hancock building and grab one of Chicago’s greatest views of the water and city. Afterwards venture over to Chicago’s Navy Pier to get out on the water via water taxi, or grab a drink and relax on the Ferris wheel while feeling the cool Lake Michigan breeze.


Words by: Kyle Rich