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TRAVEL - Chicago in Four Days (with little to no sleep)

Travel by Jason Krell and Alykhan Velji – The Style Guys (From February 2019 Online)
Image by: Adam Alexander Photography
Image by: Adam Alexander Photography
TRAVEL - Chicago in Four Days (with little to no sleep)
Image by: Choose Chicago

When we travel to a new city, we hit it hard. Forget about coming home relaxed and rejuvenated, we’re there to experience what the city has to offer, less so as tourists, but more like a local would. We do the deep dive, 20,000 steps a day, 2,000 photos and a handful of new Facebook friends by the time we return home.

Chicago has been a bucket list destination for us for a long time, but with no business travel to the city, and no personal contacts to push us to visit, it remained on the list – a big mistake! Home to 2.7 million people, Chicago is America’s 3rd largest city. It was recently named "City of the Year" by and the Boyztown community was named "best gay neighbourhood in the world" by Out Traveler Magazine.

If this wasn’t enough to draw us in, we also learned that the week we were available to go was Pride - one of America’s largest – so the stars felt aligned.

Leaving on a Thursday from Calgary, the flight is a super easy three hours, and with only a one-hour time difference, visiting The Windy City for a long weekend is a breeze. The bigger problem here was deciding what we could endeavor to see and do, where to eat, drink, take in Pride activities, and not come home in tandem body bags. Clearly, we needed the help of some Chicagoans to point us in the right direction, and fortunately they were all willing to help.

You’ll find that the people of Chicago are proud of their city! Friendly, funny, and open, it’s not difficult to make a real connection with a local. We were fortunate enough to meet a group of guys on day one at Navy Pier Pride ("Queer the Pier" they were calling it). We found the event online and were drawn to promise of the headliner that evening – CeCe Peniston. At first, we were a little bit underwhelmed by the small crowd of the event, discovering it more of a family event - and given the distance between it and Boyztown it made sense - but we soon discovered that we were in exactly the right place.

CeCe was a delight! She got the crowd bouncing, she was funny, and her voice could have filled a stadium. The mixed, unpretentious crowd danced in the square and towards the end of her set we enjoyed fireworks overhead. Our new friends, a crew of Mexican-American Chicago locals quickly took us under their wings and invited us to join them at of the weekend’s festivities.

Off to Boyztown. An almost 30-minute drive from the Pier, we understood why the crowd was thin at Navy Pier. The streets were packed with club-goers, rotating from bar-to-bar, lining up for a drag show, DJ, or simply chasing the party. Given the Chicago assignment, we couldn’t resist popping our heads into multiple bars to get a feel for the scene and offer solid reporting.

Your first stop might be Roscoe’s Tavern, a long-time favourite, well-known for regular events. We were in luck because that night we were about to see one of our favourite Drag Race performers – Shangela. Halleloo! The club was overpacked, but we kept an eye on the nearest emergency exit (and bar) and squeezed our way through to the front of the stage. Serving all the fish, the laughs, a few heartfelt pride moments too, we absolutely got our door cover’s worth.

Right across the street is Progress Bar (yes, there are a lot of options in this area). Small, clean, stylish, you get more than a vodka & soda in a plastic up, here proper cocktails and martinis are mixed under the giant cloud-shaped lighting installation made of hundreds of white bulbs.

If you’re looking for the Big Gay Disco, next door is Side Track. Multiple rooms, bars, large screens, and a huge outdoor patio, Side Track is not where you want to get split up from your group with a dead phone. Every day and night is a new adventure here, so visit their website and plan ahead.

And if go-go dancers are your jam, go see what’s shaking at Hydrate. On one side you’ll find them on the bar, head through the door and another night club reveals itself, this one darker and more like a circuit party, featuring DJ’s and the ‘Honeys on Halstead’ Drag Show.

Of course, the highlight of most Pride weekends is the parade, and Chicago’s is one of the country’s largest with over 150 floats, performers and bands. The streets are busy, so bring all you need or risk getting caught in a sidewalk stampede. We met up with our new friends near Halstead, W Grace and N Broadway, a spot complete with chairs, coolers, more new friends and family, and the highlight, a speaker and generator to keep the music going when there was a break in the floats! This, our friends, is how you PRIDE!

2019 will be the 50th annual pride parade in Chicago, so consider booking early! Of course, give yourself a few extra days before and after to enjoy all that Chicago has to offer beyond the festivities – you’re sure to have an incredible time whatever your interests and wherever your 20,000 steps take you.

Where to stay

The Viceroy
Located in The Gold Coast strict, the Viceroy is for those who want the high style that chain is known for. 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. 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!).  

The Blackstone, Autograph Collection

This landmark hotel is located on The Cultural Mile. Originally built in 1910, 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 and luxe. In 2017 the hotel was completely revitalized and now boasts a glorious collection of local art throughout the lobby, gallery and the common spaces. Blackstone suites have incredible views of Lake Michigan, Grant Park, Buckingham fountain, and Boeing gallery.

Hotel Robey

Tucked away from the main tourist areas of Chicago, The Robey is in Wicker Park and stands high above the intersections of Damen, Milwaukee, and North Avenues. With its unique triangular footprint, no corner has been un- touched in this gorgeous rejuvenation. Relaxed and casual, this Art Deco boutique hotel includes Cafe Robey, a rooftop pool, and another rooftop bar called the Cabana Club.

Where to Eat

Raised Rooftop
While it’s not the highest rooftop on the list, it actually has one of the best views. Instead of being above the action, you feel a part of it. Raised has a more industrial aesthetic and raw finishes, contrasting the sparkling view and top-end sharable plates. High points for the delightful, unpretentious staff.


Located inside the Viceroy, Somerset is part of one of Chicago’s most notable restaurant groups – Boka. The two-story 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 Mushroom Bolognese.


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. From the outside you might think you’re entering a night club (which it once was) but once inside you’ll see the grand staircase and sparkling chandeliers overlooking the vibrant lounge scene.

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.

Chicago Experiences

Unwind at Aire Ancient Baths
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.

Get Physical with a 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, get fit at the zoo, or even from the 94th floor observation deck at 360 Sky Yoga. We also discovered Chicago’s version of The Highline in New York, The 606, the city’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.  


The Magnificent Mile is a no-brainer, hit up the over 460 retailers including big name department stores and luxury brands. If vintage and eclectic is more your style, browse the shops in Wicker Park – most notably, visit the Adidas Originals Flagship Store and Vintage Underground for clothing, accessories and other treasure. You can also get custom by making your way to Laudi Vidni (individual spelled backwards) and build your own leather goods, including bags, wallets, handbags, passport holders and more. You choose the leather, lining and hardware or from their beautiful in-store collection.

The Sites

No trip to Chicago would be complete without taking a 90-minute Architecture River Cruise with Chicago’s First Lady. 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), guides 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!

Get your selfies in at Millennium Park. More than just the iconic ‘bean’ Millennium Park is like the new kind of town square, a place for concerts, fitness, and other activities. Walk through the entire area and stop at Cloud Gate (the bean), which is made of seamless stainless steel, reflecting the city from all angles. Don’t miss Crown Fountain where you’ll see kids anxiously anticipating the ‘spitting’ water to cool them on a hot day, The Art Institute of Chicago, and the Buckingham Fountain to the West in Grant Park.

See Chicago’s top 5 attractions with a Chicago Citypass. A great way to check all of the must-do’s off you list and save money while you to it, this includes VIP admission to:

Shedd Aquarium

Skydeck Chicago

The Field Museum

Adler Planetarium or Art Institute of Chicago

Museum of Science and Industry or 360 CHICAGO Observation Deck

*Other packages are available if that’s still not enough for you!

Related Articles

Contributor Jason Krell | Alykhan Velji |

Locale Chicago |

Topic Accommodation and Lodging | Food | Travel |

Photo Gallery Chicago | Travel |


The Viceroy
Image by: Christian Horan
The Viceroy
Image by: Christian Horan
The Blackstone
The Blackstone
Hotel Robey - Cabana Club
Hotel Robey - Cabana Club
Chicago's First Lady
Image by: Adam Alexander Photography
Image by: City of Chicago
Chicago Pride
Cafe Robey
Cafe Robey
Aire Ancient Baths
Aire Ancient Baths

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