DEC 2023

From secret bars to rooftop thrills, experience Chicago's unique wonders!

Welcome to your ultimate guide to exploring the offbeat, exhilarating side of Chicago. 

Whether you're a local looking for new adventures or a visitor seeking something beyond the typical tourist attractions, this blog post is your ticket to a world of unique experiences. 

From the mysterious allure of hidden speakeasies to the adrenaline rush of rooftop adventures, Chicago is a city brimming with surprises waiting to be discovered. 

So, buckle up and prepare to dive into the heart of The Windy City like never before!

Whispered secrets and craft cocktails in surreptitious speakeasies

Craft cocktail on a vintage barrel in a Chicago speakeasy.

Enjoy enchanting elixirs in select bars.

Step into the clandestine world of Chicago's speakeasies, where the spirit of the Prohibition era lingers in every sip. 

Hidden behind unmarked doors and disguised facades, these secret bars offer more than just exquisite craft cocktails; they provide an immersive journey into a bygone era.

The Violet Hour and Room 13

In neighborhoods like Wicker Park and the Loop, whispered codes and secret knocks open the way to places like The Violet Hour and Room 13. 

  • The Violet Hour, with its unassuming façade, reveals a world of artisanal drinks and plush, vintage decor; it’s also a top destination for Valentine’s Day.

  • Room 13, an exclusive members-only bar, transports you to the 1920s with its authentic Prohibition-style experience.

Green Door Tavern

But the adventure doesn't end there. 

Seek out the Green Door Tavern, where a concealed door in the back leads to an intimate speakeasy known for its unique ambiance and handcrafted cocktails. 

This place, steeped in history, is a testament to Chicago's rich and occasionally illicit past.

Thrilling & high-adrenaline urban adventures

An overgrown abandoned building for urban adventure in Chicago.

Embrace the wild side of The Windy City!

Venture off the beaten path and experience the adrenaline rush of urban exploration in Chicago. 

From exploring abandoned spaces, to hitting the dopamine highs of parkour, the Windy City has a treasure trove of experiences for you to explore.

Our underground streets

Delve into the depths of Chicago's unseen streets with a journey through Lower Wacker Drive and Lower Michigan Avenue. 

These underground roads, iconic for their appearance in films like The Dark Knight, offer a unique urban exploration opportunity, revealing a lesser-seen side of the city's bustling life.


For those craving a more heart-pounding experience, Chicago's urban landscape offers thrilling opportunities for parkour. 

Public spaces like Grant Park & the UIC campus and dedicated gyms like Parkour Ways, with their dedicated parkour courses and climbing walls, are perfect for both beginners and seasoned practitioners to push their limits under the skyline of the Windy City.

Mind games and mysteries in escape rooms

Engaging scene from our (Fox in a Box's) Bank escape game.

Peeking into the hidden locker in our game The Bank!

Tired of the usual escape game themes? Looking for something beyond prison escapes and zombie outbreaks?


From Cold War suspense to mobster intrigue - there’s a host of offbeat escape game themes waiting to be explored in Chicago!

Fox in a Box Escape Rooms (yep, that’s us)

While our escape games do include a quintessential prison break, you can also check out:

  • The Bunker, which is set in the Cold War,

  • The Bank, which sees you mastermind a bank heist, and…

  • Zodiac, where you have to escape a psychopath while trying to figure out who he or she is (or isn’t)

PanIQ Escape Room

Another gem in Chicago's escape room scene is PanIQ Room, renowned for its creatively themed adventures. Standout experiences include:

  • Wizard Trials, in which you seek to prove your mettle in wizardry, and

  • The Red Wire, which sees you become secret agents warding off an attack.

Artfully crafted recipes and unique dining experiences

An innovatively presented, gourmet dish showcasing Chicago's culinary creativity.

More than just taste - it’s art on a plate!

Of course we all know and love Chicago's traditional cuisine, but the Windy City has a culinary landscape that stretches far beyond, blending creativity with flavor in every bite. 

Food can become an art form, an adventure, and a story waiting to be savored.


This Michelin-starred restaurant, led by Chef Grant Achatz, is famed for its theatrical presentation and inventive dishes. 

Imagine a balloon made of apple taffy or a dessert painted directly on your table - dining here is an experience that engages all senses.

EL Ideas

Then there’s the avant-garde EL Ideas, where the dining experience is as unconventional as the menu. 

Here, guests are encouraged to interact with the chefs in a relaxed, intimate setting, making each meal a personal and memorable journey.


For those craving global flavors with a local twist, Noodlebird presents an intriguing medley of Chinese, Portuguese, Indian, and African cuisines. 

Their menu, featuring items like the minced soy sauce beef rice bowl and spicy jumbo shrimp, offers an innovative culinary experience that's both eclectic and delightful.

Head inside Chicago's underground music and art havens

DJ performing at an underground music event in Chicago.

Feel the pulse of Chicago's underground music and art - where creativity knows no bounds.

Dive deep into the heart of Chicago’s artistic soul with its vibrant underground music and art scenes. 

Tucked away in the city’s eclectic neighborhoods, these creative spaces pulsate with raw energy and innovative expressions.


Experience the electric atmosphere at spots like Smartbar, where underground DJs spin everything from techno to indie, igniting the dance floor with an infectious energy. 

This legendary venue has been a cornerstone of Chicago's nightlife for decades, showcasing emerging artists and celebrated DJs alike.

The Flatiron Arts Building

The artistic journey continues in spaces like The Flatiron Arts Building, a sanctuary for local artists. 

Its labyrinthine halls, filled with studios and galleries, burst with the works of painters, sculptors, and performance artists. 

Monthly open-house events invite art enthusiasts to mingle with creators, offering a glimpse into the city’s dynamic art scene.

Not your usual bar hopping and pub crawls

Participants enjoying a themed pub crawl event in Chicago.

Dive into Chicago's spirited pub crawl scene!

Choose from a kaleidoscope of themed Chicago pub crawls, each providing a unique way to experience the city’s diverse bar scene. 

These aren't just typical nights out; they're curated adventures that combine fun themes with socializing. 

Here are some of the most exciting ones:

  • The Twelve Bars of Xmas (TBOX): Revelers, often in holiday-themed costumes, hop from bar to bar, enjoying special drinks and merry activities in this legendary crawl in Wrigleyville.

  • The Chicago Zombie Pub Crawl: Held annually in Andersonville, this event sees participants donning their best zombie attire and makeup, shuffling between local bars for themed drinks and apocalyptic fun.

  • Screw Cupid Pub Crawl: A celebration of being single, in defiance of Valentine’s Day. This crawl in Wrigleyville offers food, domestic beers, and trolleys for transportation.

  • The Mustache Crawl: Flaunt your 'stache and enjoy promos from various brands, with proceeds going to local foundations like the Lakeview Pantry. And yes, fake ‘staches count!

Virtual worlds and digital dreams in the Windy City

Vibrant digital art display in a futuristic tech experience.

Art meets technology in Chicago's digital realms.

Chicago isn't just a city steeped in history; it's a forward-looking metropolis where the future is already happening. 

For tech enthusiasts and digital art aficionados, the city offers an array of experiences that blur the lines between reality and virtual wonder.

VR venues

For a taste of the high-tech gaming world, head to places like Ignite Gaming Lounge or The Raven Room (formerly Redline VR)

These arcades take gaming to the next level with state-of-the-art virtual reality setups, providing an escape into alternate dimensions.

Chicago Architecture Biennial

Art and technology also converge in events like the Chicago Architecture Biennial, which often features digital and interactive installations showcasing futuristic concepts in urban design.

One example would be Cardboard Merzbau by Barkow Leibinger, a site-specific installation that transforms spaces using cardboard tubes, embodying contemporary environmental and urban design ideas.

Festivals & fairs that unleash a kaleidoscope of culture

Vibrant scene at a bustling street fair with colorful stalls and lively crowds.

Immerse yourself in the lively tapestry of Chicago's street fairs.

Experience the heart and soul of Chicago at its most vibrant and colorful through the city's eclectic mix of festivals and street fairs. 

From the bustling streets of Wicker Park to the lively avenues of Pilsen, each festival paints a unique picture of Chicago's diverse communities and rich cultural tapestry.

Renegade Craft Fair

Take a stroll through the Renegade Craft Fair in Wicker Park, an epicenter of creativity where local artisans showcase their unique crafts, art, and handmade goods. 

This is more than just a market; it's a celebration of Chicago's thriving independent art scene.

Chicago SummerDance

Don't miss the Chicago SummerDance in Grant Park, a festival that invites you to sway to the rhythms of salsa, swing, and waltz. 

It's a testament to Chicago's love for music and dance, set against the backdrop of the city's stunning skyline.

Rooftop wonders and sky-high thrills

Breathtaking view of Lake Michigan from a high-rise rooftop in Chicago.

Elevate your Chicago experience with a mesmerizing view from the city's soaring rooftops.

Rise above the bustling city streets and discover a different side of Chicago, where the sky is the limit and the views are unparalleled. 

Chicago's rooftop adventures offer a unique blend of relaxation, entertainment, and stunning panoramas, making them a must-visit for locals and tourists alike.

Cindy's Rooftop

For an elegant rooftop dining experience with a view, Cindy's Rooftop is a gem not to be missed.

Located atop the Chicago Athletic Association Hotel, Cindy's offers a panoramic view of Millennium Park, Lake Michigan, and The Art Institute of Chicago. 

The atmosphere is matched by a menu that features fresh, locally sourced ingredients, perfect for a brunch with a view or a romantic dinner under the stars.


Adrenaline seekers can test their limits at 360 CHICAGO's TILT, an exhilarating attraction that literally tilts visitors over the edge of the skyscraper.

Located on the 94th floor of the John Hancock Center, TILT extends out over Michigan Avenue, offering a unique, sky-high perspective of the Magnificent Mile and beyond.

Unveiling the nighttime magic of Chicago's streets