Chi-CAH-go! The windy city. The second city. The middle city. Gotham.
This weekend was my second such trip to the capital of the Midwest, the first in 2011Â at the tail end of winter, when I had no chance onÂ foot to absorb the environment and neighborhoods. In the agreeable weather of August, I could better develop my sense of the place.
I feel a special connection to Chicago, not because I have family roots there, but because it has been portrayed by figures in my life and in no small part by the pop culture I grew up loving. John Hughes dominated the 1980s with sweet stories about the North ShoreÂ suburbs, while movies like BackdraftÂ and Candy ManÂ highlighted the city’s coarse edge.
Unlike other American metropolises that to me, are categorically one-, two-, or three-dimensional, Chicago presents many facets across its both lopsided and symmetrical landscape. It has no east side (it would all be under Lake Michigan) but radiates out from the north-south axis of the lakefrontÂ in perfect concentric half-circles.
Urban Planning & Architecture
In many ways, it is the archetypal planned American city, with a central business and retail core (the Loop), surrounding industrial and high-density residential areas, followed by leafy neighborhoods and then finally, past the city limit, refined suburbs with their own commercial cores. All this, connected by highways, commuter rail (Metra), and an inner-city rail system (the L). Plus, an urban bikeshare network and robust pedestrian focus.
After the fire of 1871, much of the central part of Chicago was rebuilt using the first community master plan, which inserted more green spaces and beautified the streetscape, among other things you can still enjoy today, like the 18-mile Lakefront Trail, which spans the entire length of the city.
Outside of its many green spaces and transportation network, Chicago is built upon a virtually unbroken grid of rectangular blocks, with alleys, side streets, and arterial collectors. Some streets span the entire city, an endless series of intersections and streetlamps, dotted with bars, grocery stores, and churches. Depending on which part of Ashland Avenue you’re on, you could be in Little Italy, Wicker Park, or Edgewater.
I once called Chicago, outside of the Loop, the Brooklyn of the Midwest.Â I can’t blame myself for trying to describe theÂ city in terms of others I know better. Chicago is an enigmatic beast, however, and makes simple comparisons never quite accurate, though many parallels do exist.
While it has its feet grounded in friendly Midwestern hospitality, which is rooted in simplicity and tradition, Chicago has as much of an academic, cultural, and innovative history as its main global counterparts. The Shoreline Architecture Tour is one way to understand the history of the Loop vicinity, and see how the city has informed architecture, engineering, and urban planning for much of its history. A former New College classmate, Becky Marshall, will tell you all about it.
Two unique Chicago contributions to the world:
- Mies van der Rohe “skin & bones” modern skyscraper architecture, which is comprised almost entirely of steel skeletons and glass siding.
- Bundled Tubes construction for skyscrapers, seen most prominently in the Willis (Sears) Tower, and now used to construct the world’s tallest buildings.
Encapsulating its appeal, for which it has plenty of, is a challenge. Chicago exhibits both in its culture and population the principles the U.S. of A. was founded on (separation of church and state, industry, free enterprise, and trade), without the conservatism we now associate with modern “American patriotism.” It is family-friendly without being exclusionary, and meshes ethnic enclaves along invisible topographic borders. Unlike San Francisco and Boston, sprawling urban and suburbanÂ development has scarcely been bounded by bodies of water or mountains.
Fitting to its geographic position, it is the best of both coasts, without the haughty cosmopolitanism of New York or inherent vanity of Los Angeles. Its main and only drawback is the long, dreary winter. And though the cold has a way of uniting its citizenry, the city is not without its extreme disparities, with big-cityÂ glamour in one area (e.g. The Gold Coast‘s high dollar-per-square-foot retail sales) and shocking poverty in another (all of the South Side’s high murder rate).
This is all to say, not succinctly, is it is one my favorite cities, for reasons I cannot easily convey. Maybe I like that its complexityâ€”unlike other places I could easily ‘figure out’ in a weekend or two. That is why I made a point to join my friend Chris at Market Days, even though I leave for Milan in a few short weeks.
In order to make the most of its warmer months, the city transforms itselfÂ into an outdoor playground, making use of its myriad parks and miles of public lakefront. Every weekend presents a festival or specialÂ event. Streets are shut down, and visitors join residents to party in the street, between brick facades, under an intense summer sun.
Northalsted Market Days feels a lot like Pride, only without the parade. Instead, vendors line the street and bars open their doors and windows to three days of revelry and music.
If you’ve ever been to a gay event, you know what to expect: all manner of half naked men, in various forms of physical fitness, and a lot of colorful, eccentric characters representing the best of the marginalized. I probably take it for granted, since it usually devolves into sex, excessive drinking and drugs, and always means crowds, lines, and waiting. You won’t catch me clamoring for any of that.
I did however unexpectedly click with a guy named Rob, whom aside from his ‘Alpha’ dog chain choker, was friendly, genuine, handsome, and unabashed in his status as an HIV+ young man. He was a refreshing look into the chapter of gay culture I rarely encounter, and have (probably) unfairly judged.
I balanced the intensity of drinking and flirting in Boystown with trips to other neighborhoods, and the activity I’m most comfortable in: shopping.
Chicago certainly isn’t known for its style, since the necessity half of the year is pure warmth in bulk. However, the Magnificent Mile area, plus commercial districts in secondary neighborhoods, provide a diverse shopping experience on par with places like Dallas, Houston, DC, and San Francisco.
My favorite stop on East Oak Street, and the most modern of the department stores, is Barney’s New York. Its six floors house a curated collection of goods from the best big and small designers and labels. It has moved upmarket since I was last there, with Barney’s in-house collection and diffusion lines like John Varvatos Star USA squirreled into a single corner.
The rest of the men’s two floors are dominated by an impressive selection of Saint Laurent, Rick Owens, Balenciaga, and the like, with impeccable niche brands in contrast. I found a Harris Wharf London bouclÃ© sport coat that fit perfectly.
If you haven’t visited the basement of a Barney’s store lately to sample the fragrances and cosmetics they stock, like Frederic Malle and Sunday Riley, you should!
Bloomingdale’s, Saks Fifth Avenue, and Neiman Marcus were all a let down, feeling stodgy and old-fashioned in the shadow of Barney’s.
Nordstrom anchors the southern end of Michigan Avenue, and has just undergone a thorough renovation, with a sparkling new Prada hard boutique for women’s and men’s accessories. The mens floor (on the 2nd level) is still mid-refresh, but manages to hobble along with a selection of trendy lines like The Kooples, T by Alexander Wang, Belstaff, and DSquared2.
Chicago is home to the only other Church’s English ShoesÂ US store outside of New York. Stop into this gilded shop for my favorite penny loafer, the Pembrey. It comes in black or brown leather, as well as brown and navy suede.
In Old Town, I found myself inside GREER, one thing that Chicago is known for. The craft, paper, and D-I-Y emporium is full of greeting cards, decorative everything/anything, and some fantastic writing instruments. After, go next door for a Bliss Bite at Cocoa + Co. It’s a spoonful of melted chocolate with your choice of toppings!
If you go…
- Sunda, an Asian restaurant with fantastic everything, from sushi to fried rice
- Angelina, where we had delicious brunch
- Velvet Taco, where tacos are made from a variety of global cuisine influences
- Old Chicago Inn, a B&B that is more like a summer at grandma’s than a hotel, but charming nonetheless
Also see my Map of Chicago Places, and Chicago Board on Pinterest. Many thanks to my friend Rob, for hosting me the first night. And, to Chris for organizing the trip!