Architecture is the platform where earth and sky meet, and Chicago is one of the best places in the world to experience it. While river boat and walking tours remain popular ways to experience Chicago’s iconic skyline, we joined Chicago Helicopter Experience Tours to gain a unique aerial perspective of the city. In this article, we explain why Chicago’s architecture is best appreciated from above.


CHICAGO, Illinois – One of the most unusual things about the city is its river. It flows backward!

In 1900, to address a decades-old problem of protecting the city’s drinking water from pollution and waterborne diseases, local officials came up with a plan to reverse the flow of the river from Lake Michigan, its original outlet, towards the Mississippi in the opposite direction.

Chicago Riverwalk | Chicago's architecture

This feat of engineering is just one of the many examples of Chicago’s ingenuity. However, it is with its architecture that Chicago’s innovation really comes into its own.


Choose Chicago!

Chicago is one of America’s most diverse cities; a characteristic that is inextricably linked to the westward growth of industry, transportation, and trade in the mid-1800s. The resulting effect is a city with a rich history and whose cultural tapestry includes diverse neighbourhoods, music, food, and art.

Navy Pier | Why Chicago’s Architecture is Best Appreciated from Above

With many direct daily flights from London to Chicago’s O’Hare International Airport, it is always easy for us to choose Chicago as a layover destination when visiting the American Midwest.

Besides, Chicago has enough to keep visitors coming back again and again!

On our first visit, like many first-time visitors, we restricted our itinerary to the area in and around ‘The Loop’, Chicago’s downtown area and central business district.

Chicago's architecture | Hancock Tower

We looked forward to visiting more working class neighbourhoods like Pilsen (where early Irish, German and Czech first settled but which is now definitively Hispanic), Bronzeville (a prominent African American neighbourhood) and Wrigleyville (home to the World-Series winning Chicago Cubs).

Chicago skyline | Hancock Tower

However, we were content to save those adventures for another, potentially longer visit. We ditched our car at our rental apartment, boarded the subway into The Loop and got off at Randolph/Wabash to begin exploring.

Pausing at the corner of Michigan Avenue and Wacker Drive, we were greeted by the imposing sky-blue Trump Tower and thus began our education on the city known as the ‘birthplace of the skyscraper’.

There are several ways to enjoy Chicago’s architecture including: on foot, from the river and from the sky.


The Chicago skyline – The view from the ground

Many cities begin life around major waterways (in this case, the Chicago River) before spreading outwards. Those rivers often become the focal point for exploration.

Navy Pier | Why Chicago’s Architecture is Best Appreciated from Above

With several walking routes to choose from, we chose a Riverwalk route starting from North LaSalle on the south bank, heading towards Navy Pier on the lake shore.

While taking in the architecture along the river, you can watch weekend kayakers and water taxis navigate the river on a sunny afternoon; enjoy ‘Brunch and Blues’ at River Roast Restaurant where waiters expertly carve up your roast with the backdrop of a live band paying tribute to Chicago’s blues legends; and get lost in the crowds at Navy Pier.

The do-it-yourself approach also gives you a chance to explore some of the classic Chicago-style bascule bridges that criss-cross the river. These bridges are as much a part of the architectural landscape as the glass, steel and brick towers built in a variety of styles on both sides of the river.

Chicago Riverwalk | Why Chicago's architecture is best viewed from above

HDYTI Tip: River boat tours are a popular way to see the architecture along the trisected branches of the Chicago River and to learn the stories behind famous buildings.

While the view from the ground is noteworthy, an aerial view provides a wholly unique experience.


Taking to the skies above Chicago

360 Chicago | Why Chicago’s Architecture is Best Appreciated from Above

On our next visit to Chicago, the city was still buzzing from the Cub’s historic World Series triumph. Despite the recent negative press about violent crime rates, there was an air of optimism in the city.

Speaking to a conference of tour operators in 2014, Mayor Rahm Emanuel presented an ambitious target of 50 million visitors a year by 2020. We met a number of entrepreneurs whose investments in new and unique visitor experiences seemed to validate the Mayor’s bold predictions.

360 Chicago | Why Chicago’s Architecture is Best Appreciated from Above

One of such entrepreneurs is Chicago Helicopter Experience Tours (CHE), a team of experienced pilots and hospitality professionals who aim to give visitors an unobstructed view of the scale of the city’s architectural ingenuity; one that is impossible to fully appreciate from the ground or river.

CHE’s business development director, Chris Meegan explained to us that Chicagoans take great pride in their city. He believes that CHE offers a great way to showcase the city’s uniqueness and leave a lasting impression on visitors.

[clickToTweet tweet=”‘She is a novelty; for she is never the Chicago you saw when you passed through the last time.’ – Mark Twain” quote=”‘She is a novelty; for she is never the Chicago you saw when you passed through the last time.’ – Mark Twain”]


Chicago’s Architecture – Where earth and sky meet

Our scheduled flight time for their ‘Twilight Tour’ was 7 pm. To pass the time, we decided to spend the early part of the afternoon tasting our way across downtown.

A ‘Best-in-Chow’ food experience proved that there was indeed substance to the hype about Chicago’s cuisine as we sampled deep-dish pizza, hot dogs and Italian beef among other dishes.

360 Chicago | Why Chicago’s Architecture is Best Appreciated from Above

With twilight approaching, we headed south from The Loop towards the CHE-owned heliport on S. Halstead Street, arriving thirty minutes before our scheduled flight time to complete registration, security and safety checks.

A warm welcome by the CHE Tours team went a long way towards calming our nerves. The customer experience was further enhanced by a comfortable lounge area which included a 3D helicopter flight simulator and a games area for children.

Chicago Helicopter Experience | Downtown Architecture and Skyline

Feeling more relaxed after a short wait, we completed the final safety briefing before being ushered to the landing zone. Carefully following instructions, we were soon strapped in, adorned with headsets and microphones and ready to fly.

The single-engine Eurocopter AS350 B2 sat one pilot and six people comfortably, with each seat providing decent 180-degree views. The exhilarating 15-minute flight took us north along the shores of Lake Michigan towards Navy Pier before returning to base.

We flew over revellers at the Lakeshake Festival on Northerly Island and spotted Wrigley Field in the distance. Neat patterns were interrupted by the individuality, design, and detail of Chicago’s skyscrapers.

The spires of the iconic Willis and John Hancock Towers reached for the sky, dwarfing other iconic landmarks. Only at that elevation is it possible to appreciate the interplay between green space, water, and urban development.

Our friendly pilot dropped us back at the heliport where the experience ended with a non-obligatory photo beside the helicopter.

It was Sir Winston Churchill who said, “We shape our buildings; thereafter they shape us.” The Great Chicago Fire of 1871 destroyed most of the city. However, the reinvention of the city that followed became an embodiment of the character of Chicago.

Cities start life from the ground but it is their upward growth, that bold reach towards the sky that firmly establishes their ambition. An aerial view of Chicago’s architecture proves a marriage between earth and sky is possible.


Planning your Chicago trip

We’ve curated the resources below to help you plan your trip to Chicago.

CIty Pass | Chicago Tourism

CHOOSE CHICAGO offers a CityPass that gives you VIP access to five top attractions, including 360 Chicago & Skydeck Chicago (both offer impressive views over the city).

BOOK your Chicago hotel stay through our site

VISIT Chicago Helicopter Experience Tours to book your flight.

WATCH our TravelCast video below to plan your itinerary


Many thanks to our collaborative partners Chicago Helicopter Experience, Chicago Food Planet, Choose Chicago, and River Roast for the tours and amenities featured in our article. All thoughts, opinions, and photographs remain our own.



Co-Founders & Curators at HDYTI

Eulanda & Omo Osagiede are London-based freelance writers and award-winning social influencers who run the popular travel, food, and lifestyle blog HDYTI (Hey! Dip your toes in).