Maybe you’ve found yourself wandering amidst the skyscrapers of New York, feeling that uncanny blend of awe and slight disappointment—awe at its grandeur and disappointment because, perhaps, it didn’t quite meet your life-long expectations.

At least, that’s how I felt when visiting the Big Apple back in June this year. I’d waited a lifetime to walk the streets of this iconic city, only to find reality didn’t quite align with the dreamscape in my head.

Don’t get me wrong, I still fell for NYC the way we all do, but I couldn’t quite put my finger on the pulse of what was missing.

That was until I touched down in Chicago in July!

Chicago is the epitome of a dream come true! It’s a modern marvel bordering Lake Michigan, with its river coursing through the city’s heart.

An Electric Arrival

When you land at O’Hare Airport, you’re greeted by an intoxicating aura that teases you with the impending spectacle of Chicago’s skyline.

As your car wades through the highway, the skyscrapers in the distance beckon you closer like sirens to a sailor. You can’t help but feel exhilarated by the architectural majesty this city has championed since it built its first skyscraper.

Oh, and not just its first skyscraper, but the first skyscraper ever built! I knew New York got its influence from somewhere!

Checking In: The Emily Hotel

One of the newest chic spots is the Emily Hotel, an abode for rest and inspiration. It’s got an industrial charm tailored for the discerning working traveller. As you soak in the eclectic décor and international influences, you might spot Google’s office from your room’s window.

But what truly separates this hotel from the rest is its Rooftop Cinema—a movie experience set against the stunning backdrop of downtown Chicago. After screening iconic films like ‘Ferris Bueller’s Day Off’, you’ll feel as if you’ve claimed a piece of Chicago’s cinematic history.

Rooms at The Emily Hotel start from $309 per night.

Satisfying Your Palate

This city knows its food. The Emily Hotel’s resident restaurant, Fora, understands this too well with a menu that’s essentially a never-ending feast. From fries that can serve a battalion to a scrumptious grazing basket in your room featuring the city’s best, every meal becomes a culinary feast. Trust me, American portions are in another league – you’ll only need one portion of fries to serve an entire party of six!

And for those who can’t start the day without a little caffeine and a sweet treat, The Coffee Bar in The Emily’s lobby will set you up for the day ahead. Serving some of the best coffee I’ve tasted (and indulged far and wide!), their locally roasted Sparrow Coffee will boost your spirits to no end; combined with a freshly baked croissant from cult-favourite Dan the Baker, you’ll be a regular from day one!

Chicagoan Architectural Wonders

Venture out, and you can’t help but consider the Architecture River Cruise—your portal into Chicago’s iconic buildings narrated by passionate guides. You’ll traverse the city from the unique perspective of its waterways, with insights that enrich your appreciation for Chicago’s architectural diversity. It isn’t your run-of-the-mill tour; it’s an intricate insight into history, design, and culture. And yes, it’s a setting familiar to fans of Julia Roberts in “My Best Friend’s Wedding.”

Kayaking the Chicago River

Now, how many cities allow kayaking amidst their skyscrapers? You paddle through what feels like an urban canyon made of glass and steel, getting far more than your money’s worth in an hour and a half of aquatic adventure. But remember to prep your arms; this isn’t a leisurely stream—it’s the Chicago River.

Biking Through the Heart of the City

The Bikes, Bites & Brews Tour is a cinematic experience waiting to happen. It’s like you’ve jumped into a film montage, taking you through Streeterville, the Gold Coast, Lakeview, and beyond. We were even lucky enough to stop by the iconic Wrigley field on game day to soak in the atmosphere of Chicago’s team spirit.

The tour combines the scenic, the delicious, and the historic, pausing for deep-dish pizza, Chicago hot dogs, and local brews. Remember, don’t you dare put ketchup on that hotdog – unless you want a one-way ticket out of the city! And as you cycle past Lake Michigan, it feels like a picturesque frame pulled from a movie reel.

An Exclusive Skydeck Experience:

Breakfast at 1,353 Feet Above Chicago with Ferris Bueller’s Vantage Point

What would a trip to Chicago be without reaching for the skies—quite literally? But my Skydeck experience was not just any regular visit; it was an exclusive, private tour of the Skydeck Museum and The Ledge, all before the doors were thrown open to the general public.

The Private Museum Tour

Our journey started with a guided tour of the Skydeck Museum. Walking through the exhibits with no one else around was surreal—just our little group and the tour guide. The museum offers a fascinating 30-60-minute interactive experience that delves into the rich history of Willis Tower, the tallest building in Chicago, and outlines the city’s many highlights. If you’re seeking an educational yet fun activity, this is it. From the architectural marvels to the cultural impacts, the museum captures the essence of the Windy City in a nutshell.

Breakfast in the Sky

And let’s remember the excellent Skydeck team and their sumptuous breakfast spread, making it an extraordinary morning. Imagine digging an assortment of pastries while gazing at a sprawling metropolis beneath your feet. With coffee in hand, it felt like breakfast at Tiffany’s—except you’re 1,353 feet above Chicago.

Standing on The Ledge

But the crescendo of this entire experience was undoubtedly The Ledge. This glass balcony offers unparalleled views, extending four feet outside the 103rd floor of the Willis Tower. The glass boxes extend out 4.3 feet, giving you that adrenaline rush. I’ll admit, my fear of heights left my legs like jelly the first few attempts, but after minutes, I could have happily spent the entire day there. You’re standing in the air, overlooking up to four states!

Ferris Bueller’s Footsteps


Demi is an aspiring TV & Film writer who is currently studying for a PhD in screenwriting. She works as a freelance writer and loves exploring locations that have been made famous on our screens.

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