Beyond the famous Skydeck and luxury boutiques lie dozens of overlooked
treasures in Chicago’s most iconic locations. Like a city within a city, Willis Tower
(formerly Sears Tower) and the Magnificent Mile harbor secrets that even longtime
Chicagoans are still discovering.
Here’s your insider’s guide to these architectural marvels’ hidden spaces and unexpected delights.
Willis Tower’s Underground City
Few visitors realize that beneath the tower lies a vast concourse network connecting
to the Chicago Pedway system. This climate-controlled underground city features
artisan coffee shops, local boutiques, and rotating art installations.
The morning rush brings classical musicians performing in acoustically perfect corners, while lunchtime reveals pop-up food vendors serving authentic Chicago specialties.
The Secret Observation Deck
While tourists queue for the Skydeck, savvy visitors head to the 66th-floor sky lobby.
Though not officially promoted, this area offers stunning eastern views without the
crowds or cost.
Building tenants casually share this space with visitors who discover it, creating an authentic Chicago office tower experience.
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The Magnificent Mile’s Hidden Garden
Tucked between Michigan Avenue skyscrapers sits a peaceful rooftop garden
accessible via a discrete elevator in the 900 North Michigan building. Local office
workers gather here for lunch, enjoying skyline views surrounded by native Illinois
prairie plants.
Willis Tower’s Art Collection
The tower houses one of Chicago’s largest private art collections, displayed
throughout its public spaces. Most pieces rotate quarterly, featuring local artists’
work.
The lesser-known 40th-floor gallery specializes in architectural photography of
Chicago’s evolution.
The Historic Water Tower’s Secret Staircase
While tourists photograph the exterior, few discover the narrow spiral staircase
leading to a hidden observation platform. Originally used by pump station operators,
it now offers unique views down Michigan Avenue.
Access requires perfect timing – the staircase opens only during architectural tours.
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Willis Tower’s Engineering Floor
The 83rd floor houses fascinating mechanical systems that keep the building
functioning. Monthly engineering tours (reserved primarily for architecture students
but open to curious visitors) reveal the building’s inner workings, including its
innovative wind-dampening system.
The Magnificent Mile’s Underground Speakeasy
Beneath a popular department store lies a restored 1920s speakeasy with original
tile work. Now serving as an exclusive event space, it opens to the public during
architectural open houses and special occasions.
The Tower’s Original Blueprints
The Willis Tower’s mezzanine level displays rarely noticed original construction
blueprints and architectural models. These detailed plans reveal fascinating
alternatives considered during the design phase, including a different location and
height.
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The Hidden Catholic Chapel
Nestled within a Magnificent Mile office building sits a stunning Byzantine-style
chapel. Originally built for working professionals, it now offers daily services and
peaceful respite from shopping crowds.
The Building’s Weather Station
The Willis Tower’s 90th floor houses sophisticated meteorological equipment that
helps forecast Chicago weather. Though not officially part of tours, polite requests to
building management sometimes yield access for weather enthusiasts.
The Secret Retail Passages
A network of lesser-known passages connects Magnificent Mile buildings, offering
climate-controlled shopping during harsh weather. Local retailers tucked into these corridors often provide unique Chicago-made products absent from main-street
storefronts.
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The Tower’s Green Roof
While invisible from street level, Willis Tower’s lower-level roofs feature extensive
gardens that help manage stormwater. During the growing season, these gardens
supply herbs to several tower restaurants.
The Historic Allerton Hotel’s Hidden Club
The tip of Michigan Avenue’s Allerton Hotel once housed an exclusive club. Though
now closed to the public, its Art Deco details remain perfectly preserved, visible
during occasional historical society tours.
The Building’s Time Capsule
Few know about the time capsule embedded in Willis Tower’s foundation, scheduled
for opening in 2074. A replica display in a quiet corner of the lobby shows its
contents, including artifacts from Chicago’s past.
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The Secret Training Kitchen
Hidden within a Magnificent Mile hotel sits a test kitchen where famous chefs train
upcoming culinary talent. Weekly tastings are available to those who know to ask
concierge staff.
The Tower’s Private Library
The Willis Tower houses a small but significant architectural library focusing on
Chicago’s building history. Though primarily serving building professionals, it
welcomes serious researchers by appointment.
The Underground Concert Hall
Beneath Michigan Avenue lies a surprisingly good acoustic space that hosts
impromptu concerts. Originally designed as a bomb shelter, it now serves as a
practice space for local musicians.
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The Historic Elevator Bank
One of Willis Tower’s elevator banks retains its original 1970s design, maintained as
a historical exhibit. Sharp-eyed visitors might spot original Sears Tower logos still
embedded in the brass work.
The Secret Chocolate Factory
Hidden above a Magnificent Mile retail space operates a small-batch chocolate
maker. Their testing room offers samples to visitors who find their unmarked door.
The Building’s Innovation Lab
Willis Tower’s little-known technology testing center showcases upcoming smart
building features. Monthly innovation tours demonstrate how the historic structure
continues evolving with modern technology.
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Explore Patiently for Great Finds
These hidden gems reveal how Chicago’s iconic structures continue to surprise
visitors and locals alike. Whether you’re seeking unique views, historic details, or
quiet spaces away from crowds, these locations offer fresh perspectives on familiar
landmarks.
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