‘Eventually, I think Chicago will be the most beautiful great city left in the world’ - Frank Lloyd Wright
Since the greater Chicago area is home to over 100 houses and other buildings of Frank Lloyd Wright’s own design, this comment could be viewed as more than a little self-serving. On the other hand, when it comes to city-scape, who would know better than America’s most storied master architect. More than a collection of impressive structures, America’s Second City has carved out a niche as one of the most iconic locations in the heartland. From music and cuisine to architecture and art, today’s Chicago is a midwest Mecca of culture, inexplicably perched on the soggy shores of Lake Michigan.
However, that isn’t all that comes to mind when someone mentions the Windy City. Also known colloquially as ‘The Dark City’, Chicago has historically been associated with grittier aspects such as pollution-causing industry, animal processing plants and poverty.
Inseparably linked to villainous icons like Al Copone and John Dillinger, Chicago has also developed a reputation as a dangerous hub of crime, both organized and sporadic. In lieu of trying to bury or ignore these sinister facets, proud natives seem gratified to have forged a great metropolis out of some murky material.
Rather than try and tease out the truth between these two contradictory Chicago narratives, I want to focus on a few points of light in this town that still holds onto its own darkness. In this cultural guide to Chicago, let’s bring the dark city to light by exploring the architecture, cuisine, music and fine arts.
Since the greater Chicago area is home to over 100 houses and other buildings of Frank Lloyd Wright’s own design, this comment could be viewed as more than a little self-serving. On the other hand, when it comes to city-scape, who would know better than America’s most storied master architect. More than a collection of impressive structures, America’s Second City has carved out a niche as one of the most iconic locations in the heartland. From music and cuisine to architecture and art, today’s Chicago is a midwest Mecca of culture, inexplicably perched on the soggy shores of Lake Michigan.
However, that isn’t all that comes to mind when someone mentions the Windy City. Also known colloquially as ‘The Dark City’, Chicago has historically been associated with grittier aspects such as pollution-causing industry, animal processing plants and poverty.
Inseparably linked to villainous icons like Al Copone and John Dillinger, Chicago has also developed a reputation as a dangerous hub of crime, both organized and sporadic. In lieu of trying to bury or ignore these sinister facets, proud natives seem gratified to have forged a great metropolis out of some murky material.
Rather than try and tease out the truth between these two contradictory Chicago narratives, I want to focus on a few points of light in this town that still holds onto its own darkness. In this cultural guide to Chicago, let’s bring the dark city to light by exploring the architecture, cuisine, music and fine arts.
Guest Post by Ben Lovell
Disclaimer: This post contains some affiliate links. If you click through and make a purchase, it won't cost you any extra. The small commission we may earn will enable Feet Do Travel to continue running.
Photo credit: Tim Granlund
Architecture
Chicago may be constructed on the shore of a Great Lake (Michigan), but it’s also raised around a river. Engineered to flow backward (to carry the city’s sewage away from their water supply), the Chicago River is by far the most efficient and elegant way to view and learn about the city’s architecture. Because the Chicago River forks deep inside the downtown, it affords visitors afloat a unique vector on many of the city’s famous skyscrapers and other architectural wonders.
My choice for seeing the city by boat, Shoreline Sightseeing is a relatively inexpensive, elegant and (most importantly) informative way to tour downtown Chicago. The well-educated, passionate guides give an uninterrupted 45-minute spiel about the city’s builders and buildings, peppered with plenty of anecdotes and amusing personal commentary. If you need to get out of the sun, there’s a lower deck complete with a full bar. For my money, I put on some shades and soaked in the city.
Chicago may be constructed on the shore of a Great Lake (Michigan), but it’s also raised around a river. Engineered to flow backward (to carry the city’s sewage away from their water supply), the Chicago River is by far the most efficient and elegant way to view and learn about the city’s architecture. Because the Chicago River forks deep inside the downtown, it affords visitors afloat a unique vector on many of the city’s famous skyscrapers and other architectural wonders.
My choice for seeing the city by boat, Shoreline Sightseeing is a relatively inexpensive, elegant and (most importantly) informative way to tour downtown Chicago. The well-educated, passionate guides give an uninterrupted 45-minute spiel about the city’s builders and buildings, peppered with plenty of anecdotes and amusing personal commentary. If you need to get out of the sun, there’s a lower deck complete with a full bar. For my money, I put on some shades and soaked in the city.
Wondering what to pack for your next trip? Let us help you with the essentials in our Ultimate Packing List for Worldwide Travel (tried and tested!
Dining
When I dine out on the town, I’m comfortable at a linen table cloth or a food truck. All I ask is that the experience be authentic, inspiring and best-in-class. Chicago affords diners plenty of amazing opportunities to dine for $5 or $500. On my last visit, I tried something from each end of this incredible spectrum.
From Michelin Three Stars...
In case you’re not familiar, the Michelin Red Guide is an annual periodical detailing the finest restaurants and hotels in the world. Funny enough, it is indeed published by the tire company of the same name. Don’t let that fool you. The Michelin Star system is the absolute gold standard for restaurant ratings around the globe. There are currently only thirteen United States restaurants that hold a Michelin Three Star rating, and the only one that isn’t in California or on the East Coast is (you guessed it) in Chicago.
When I dine out on the town, I’m comfortable at a linen table cloth or a food truck. All I ask is that the experience be authentic, inspiring and best-in-class. Chicago affords diners plenty of amazing opportunities to dine for $5 or $500. On my last visit, I tried something from each end of this incredible spectrum.
From Michelin Three Stars...
In case you’re not familiar, the Michelin Red Guide is an annual periodical detailing the finest restaurants and hotels in the world. Funny enough, it is indeed published by the tire company of the same name. Don’t let that fool you. The Michelin Star system is the absolute gold standard for restaurant ratings around the globe. There are currently only thirteen United States restaurants that hold a Michelin Three Star rating, and the only one that isn’t in California or on the East Coast is (you guessed it) in Chicago.
Photo Credit: Noah Goldenberg I was recently fortunate enough to be treated to a table at Alinea by a group of friends. Alinea is much more than a restaurant; it is an entire evening of culinary exploration. For starters, there isn’t a menu (at least not at first). You select one of three tasting experiences and then spend the next three hours discovering each course as the friendly and extensively-trained staff exposes you to it.
Because Alinea constantly reinvents its menu, I won’t be spoiling much by revealing my favorites. Some of the highlights included a Wagyu a5 steak (the finest designation in the world), a trip to the working kitchen for a custom cocktail and an edible helium balloon made of taffy. Each dish led gracefully into the next. Chaperoned by the highly-engaging tableside team, the menu evolved as the night progressed. For a final touch, the staff presented a menu for a keepsake
(and to remind us of our newly-expanded culinary vocabulary).
...To Deep Dish
Because Alinea constantly reinvents its menu, I won’t be spoiling much by revealing my favorites. Some of the highlights included a Wagyu a5 steak (the finest designation in the world), a trip to the working kitchen for a custom cocktail and an edible helium balloon made of taffy. Each dish led gracefully into the next. Chaperoned by the highly-engaging tableside team, the menu evolved as the night progressed. For a final touch, the staff presented a menu for a keepsake
(and to remind us of our newly-expanded culinary vocabulary).
...To Deep Dish
Photo Credit: Tim Granlund Because most of us haven’t saved up the credit card rewards for Michelin Stars every night, thankfully Chicago offers a battery of more economical dining options. A staple of the Chicago blue collar culinary experience, the Deep Dish pizza is a truly can’t-be-missed experience. If you’ve never understood the expression, ‘pizza pie’, you haven’t had a true Deep Dish. For our obligatory Deep Dish, we tried out Pequod’s Pizza… and weren’t disappointed. Served in an 18” cast-iron skillet, our bubbling Deep Dish pizzas were a solid 2 ½ inches thick - impossible to eat without a fork and knife. My only suggestion is to not try anything strenuous (or tight-fitting) for the rest of the evening.
Photo Credit: Sean Portwood
Music
From Chicago (the band) to Kanye West to the Blues Brothers, Chicago is known for its music. The city is full of amazing venues that range from the colossal United Center to basement dive bars. Chicagoans are also known for eskewing institutions - for making their own way. This brings me to an unexpectedly rockin’ good time.
On this last excursion, I got to experience amazing Chicago music at its most intimate. I could make some clever transition into this statement, but I’ll just come out with it: Chicago Loft Party is a woman’s apartment. And it’s also one of the most amazing shows I’ve ever been to. From opener Brandon Whyde to headliner Andrew Leahey & the Homestead it was intimate and epic - a truly unique and unforgettable Chicago experience.
From Chicago (the band) to Kanye West to the Blues Brothers, Chicago is known for its music. The city is full of amazing venues that range from the colossal United Center to basement dive bars. Chicagoans are also known for eskewing institutions - for making their own way. This brings me to an unexpectedly rockin’ good time.
On this last excursion, I got to experience amazing Chicago music at its most intimate. I could make some clever transition into this statement, but I’ll just come out with it: Chicago Loft Party is a woman’s apartment. And it’s also one of the most amazing shows I’ve ever been to. From opener Brandon Whyde to headliner Andrew Leahey & the Homestead it was intimate and epic - a truly unique and unforgettable Chicago experience.
Stage
Photo Credit: Noah Goldenberg A fitting finale to our cultural tour-de-force of the Dark City, the spark of humble humor that ignites so much of America’s comedic passion: The Second City. From an inauspicious beginning one snowy Chicago night in 1959, this quietly ferocious comedy troupe has grown from a handful of innovators in a run-down cabaret to the most influential improv comedy unit in the world. Now well-known as a farm league for Saturday Night Live, The Second City has given America over half a century of the best comic talent. From Harold Ramis and John Candy to Tim Meadows and Steve Carell, the A-list alumni of this unpresuming troupe stretches through generations.
The night of my group’s attendance, an extremely energetic and talented group of six performers showed us how America was using comedy to address some of today’s most poignant and important issues in ‘Grinning from Fear to Fear’. The company’s patented three act formula (two mostly scripted, one total improv) was a perfect mix of well-rehearsed bits, audience participation and off-the-cuff antics. The intimate setting and the amazing electricity of the performance made this experience truly remarkable. Given The Second City’s track record as a king-maker (and queen-maker), I’ll look forward to recognizing some of this cast on prime-time and being able to say ‘I saw them way back when’.
Darkness Defines the Light
Strangely, after an excursion marked by so many unforgettable experiences, my most compelling emotion upon leaving Chicago was of regret - of opportunities missed. The truth is, Chicago is not a one-trip (or a ten-trip) destination. I could spend a lifetime of sojourns to this beacon of Americana and still leave opportunities untried. For me, these cultural points of light are all the more luminous for the rich darkness of the city that spawned them. I’ll look forward to my next pilgrimage to the Dark City. Maybe, I’ll see you there.
The night of my group’s attendance, an extremely energetic and talented group of six performers showed us how America was using comedy to address some of today’s most poignant and important issues in ‘Grinning from Fear to Fear’. The company’s patented three act formula (two mostly scripted, one total improv) was a perfect mix of well-rehearsed bits, audience participation and off-the-cuff antics. The intimate setting and the amazing electricity of the performance made this experience truly remarkable. Given The Second City’s track record as a king-maker (and queen-maker), I’ll look forward to recognizing some of this cast on prime-time and being able to say ‘I saw them way back when’.
Darkness Defines the Light
Strangely, after an excursion marked by so many unforgettable experiences, my most compelling emotion upon leaving Chicago was of regret - of opportunities missed. The truth is, Chicago is not a one-trip (or a ten-trip) destination. I could spend a lifetime of sojourns to this beacon of Americana and still leave opportunities untried. For me, these cultural points of light are all the more luminous for the rich darkness of the city that spawned them. I’ll look forward to my next pilgrimage to the Dark City. Maybe, I’ll see you there.
Author Bio:
A firm believer that freedom of information improves business, travel and life, Johnny Jet contributor Ben Lovell is committed to sharing best practices.
A firm believer that freedom of information improves business, travel and life, Johnny Jet contributor Ben Lovell is committed to sharing best practices.
Book your Chicago, USA, worldwide hotel or any weekend break through our website. We always use Booking.com, and are proud to have a partnership with them. Visit our Hotel Booking page and search as normal. (If you're on a mobile/cell, turn the device horizontally, “search” will be bottom right)
 | Don’t leave home without travel insurance! To get the best quote to suit your needs, visit our Travel Insurance page. |  |