In the City of Big Shoulders – Carl Sandburg’s apt description of the Midwest’s burly and bustling metropolis – trailblazing innovation and strokes of genius are somewhat of a tradition. Here, history-making ideas from some of the twentieth century’s finest architects – Louis Sullivan, Frank Lloyd Wright, Henry Hobson, Dankmar Adler and Walter Burley Griffin, to name a modest few – shaped the city’s physical form not to mention its global identity, manifesting in design movements such as the Chicago and Prairie Schools. Present-day progressive minds ensure Chicago remains a hive of ingenuity; this century, however, it’s a pursuit of low-impact, greener living that commands praise (a course surely unimaginable to the cast of Saul Bellow’s ‘The Adventures of Augie March’, whose weathering of 1920s Chicago in all its feverish, wheezing industrial bustle provides consummate reading material for visitors to the Windy City). Welcome a new day with strong coffee in the Museum of Contemporary Art’s commendable café – on Tuesdays, wander the sun-drenched spaces free of charge. Digest the morning’s cultural nourishment at Oak Street Beach, a few blocks along North Michigan Avenue; here, locals unleash high spirits that are kept in check through famously unforgiving winters, resulting in an atmosphere of palpable, unreserved joy that ripples through the city. A few blocks south, on the ninety-sixth floor of Hancock Tower, a refreshing gin and tonic pairs well with the stunning spectacle of the Chicago’s skyline at sunset.

Agent Gallery

agentgallery.com

Slightly unsettling curios nest among odd and eerily beautiful objects, serving as Agent Gallery’s principal draw. Wander in to marvel (or gawk) at the exhibited art or to purchase practical objects for the home: furniture, lighting, sea anemone specimens etc. The by-appointment only gallery’s macabre bent makes for a museum-like visiting experience; seek out an Art Deco desk lamp or Mao-era propaganda poster; or, should tastes tend to vintage orthodontic dental mannequins and prosthetic eye collections from the 1950s, then rejoice - options abound.

Boka Restaurant

bokachicago.com

Sample Michelin-starred fare in one of Chicago’s finest dining rooms, where a sleek and dark aesthetic is tempered cleverly with a mossy vertical garden adorned with portraits of snappily dressed cats and forest creatures sporting ruff collars. Here, chef Lee Wolen celebrates humble vegetables with vigor and sass, exemplified by the brilliant broccoli salad. Meat, however, can’t help but steal the spotlight and accordingly the short rib should not be missed.

Chicago Architecture Foundation

architecture.org

Honoring the city’s indelible imprint on twentieth-century architecture, Chicago Architecture Foundation (CAF) preserves, celebrates and nourishes its citizens’ ardent respect for design. To complement a rich annual programme of lectures, events and workshops that examine the everyday importance of intelligent architecture, the Foundation’s daily tours are renowned widely for their quality, scope and depth of detail. Selecting a tour can be challenging so it’s helpful to note that those who opt for Historic Skyscrapers or River Cruise are rarely left wanting.

Dorchester Projects Archive House

rebuild-foundation.org/site/archive-house

When the Prairie Avenue Bookstore closed its doors in 2009, local artist Theaster Gates offered its 14,000-volume collection (a vital and comprehensive catalogue of the birth and life of Chicago’s Prairie School) refuge in his purpose-built Dorchester Projects Archive House. The previously derelict building, tenderly restored using repurposed materials (part of the artist’s wider urban regeneration efforts), also houses 60,000 glass lantern slides salvaged in a similar fashion from the University of Chicago’s Art History Department. Next door, explore Listening House, home to scores of albums rescued when 21-year-old Dr. Wax Records closed its doors in 2009.

Exelon Pavilions, Millennium Park

cityofchicago.org

Absorb Anish Kapoor’s ‘Cloud Gate’ sculpture (known locally as ‘the bean’) and allocate ample time to admire Frank Gehry’s Jay Pritzker Pavilion before wandering on to Millennium Park’s south end where Renzo Piano’s Exelon Pavilions reside. Clad in solar panels that feed electricity - in impressive volumes - directly into the city’s grid, the Pavilions play a key part in Chicago’s ambition to earn North America’s title of ‘greenest city’. With thoughts resting on subjects of sustainability and environmentally conscious living, wander into Lurie Garden, a three-acre rooftop botanical paradise as exquisite in winter as it is in the throes of summer.

Florida Stone Crab Claws at Shaw’s Crab House

shawscrabhouse.com

An ode to the ocean, the menu of Shaw’s Crab House centres on oysters shucked fresh from Puget Sound and meaty crab claws sourced seasonally from waters of the North Atlantic to Alaska’s Kodiak Archipelago. Happy hour – 4pm to 6pm daily – sees hordes of visitors gleefully sucking down half-price oysters – a satisfying feast best enjoyed as an afternoon pit stop between exploring nearby Chicago Cultural Center and ambling through Millennium Park.

Graham Bookshop

grahamfoundation.org

In this beautiful, light-filled bookstore devoted to architecture- and design-focused titles, a large volume of tomes on display pertain in some way to a stimulating public programme of talks and exhibitions held by the Graham Foundation for Advanced Studies in the Fine Arts; the rest are publications produced by the Foundation’s grantees (around $1 million is granted annually to organisations and individuals working on in-depth design-, architecture- and urban planning-themed projects), noted design periodicals and hard-to-find or historically significant titles.

Harris Theater for Music and Dance

harristheaterchicago.org

At the rear of Jay Pritzker Pavilion on Millennium Park’s eastern edge, Harris Theatre is home to more than forty performing arts companies. With its full house of riotously creative ensembles, the theater’s output of public events is – perhaps unsurprisingly – renowned globally. Pore over the programme, which in the past has featured performances by the esteemed Paris Opéra Ballet and Israel’s Pinchas Zukerman, leaving ample time pre-show to wander and admire the cleverly landscaped plains of Millennium Park, its garden paths, public art and spectacular architecture.

Illinois Institute of Technology

iit.edu

Home to the world’s most concentrated assemblage of buildings by Mies van der Rohe (drawn from Germany’s Bauhaus to design the institution’s master plan), IIT is as much a gallery of modernist architecture as it is a place of academic instruction. Once all buildings have been ogled to a satisfying degree, continue the tour along the shore of Lake Michigan, dotted with some of the architect’s best-known triumphs including One IMB Plaza, the Esplanade Apartment Buildings and 860-880 Lake Shore Apartments.

Johnnie’s Beef

+1 708 452 6000

As ‘Chicago’ as the Sears Tower (or as Chicagoans’ resistance to calling it by its current name, Willis Tower), Johnnie’s Beef represents the top of the mountain where the city’s beloved signature sandwich is concerned: the Italian beef. Sliced delicately thin, abundant tender beef folds into a fresh white roll, whose primary purpose is to soak up the warm juices of meat freshly dunked in Johnnie’s special jus. Specify ‘sweet’ to include green bell peppers, ‘hot’ to top your meal with the house’s fiery pickle mix, and be sure to add ‘juicy’ if seeking an especially memorable beef sandwich experience.

Khecari Contemporary Dance Company

khecari.org

Known best for performances that warp and tinker with the audience’s perceptions of space, Khecari takes contemporary dance and contorts its experimental bent a fraction further. Past sold-out seasons have seen the traditional stage abandoned in favor of Khecari’s purpose-built ‘micro-theater’, a five by eight-foot box recessed below an audience of twelve. Looking down on the intricately choreographed performance, the audience experiences an affecting, near visceral immersion in the unfolding story.

Longman & Eagle

longmanandeagle.com

For those post-hefty meal moments when rolling from the table and into bed is the most appealing idea in the world: Longman and Eagle, where six sleek and cheerful rooms were recently added to the restaurant’s offering. Designed with contemporary taste and attention to detail, the rooms vary in size and aesthetic, while each awards its lodger tokens for complimentary whiskey (the establishment’s specialty). Bedside reading material usually includes Lucky Peach and Walt Whitman poetry, if not an old cassette player and mixtapes compiled by local artists.

Museum of Contemporary Photography

mocp.org

Across three floors of its compact space, Columbia College’s Museum of Contemporary Photography exhibits works of widely varied technologies, forms and techniques. Straddling analog and digital imagery produced a refreshing blend of established and emerging photographers, the museum’s catalogue is revealed through innovative programming that responds to global goings-on, historic anniversaries and the ever-changing tides of local sentiment.

‘Native Son’, 1940

By Richard Wright

While traveling, experience of a city can be enhanced immeasurably by delving into literature that explores the destination’s landscape, character and history. Published in 1940, Wright’s ‘Native Son’ was written to jar with a white readership in hopes of stoking greater awareness of the plight of African Americans suppressed under segregation, and to provoke political action. A powerful and provocative read, the book sold in record numbers at lightning speed. Pick up a copy at Logan Square’s Uncharted Books or Myopic Books in Wicker Park.

Oak Park

cal.flwright.org/tours

Like an open-air museum of architecture, Oak Park’s streets are often dotted with design aficionados on a specific sort of pilgrimage: this bosky residential nook of Chicago is home to twenty-five buildings designed or remodeled by Frank Lloyd Wright – a density unrivalled elsewhere in the world. While most are private residences, it’s possible to wander through Frank Lloyd Wright Home and Studio as part of a tour (consider ‘Wright Around Oak Park’, a three-hour guided walk) focused on Wright’s pioneering influence as part of Chicago’s Prairie School.

Poetry Foundation

poetryfoundation.org

Shared monthly, Poetry hasn’t slowed for a second of its 113-year life. Rather, when the magazine’s Foundation finally lay down permanent roots on West Superior Street in 2011 (in a refined and understated building by local practice John Ronan Architects), it opened itself to regular tours of its light-filled library (home to more than 30,000 volumes), a wider programme of events, and, loveliest of all, Wednesday Poemtime: weekly sessions devoted to cultivating poetry appreciation in two- to five-year-olds. Should you wish to secure a tour, phoning ahead is advisable.

Quiche at Floriole

floriole.com

Made using organic flour and sugar sourced locally from sustainable farms, Floriole’s French-influenced offering is one of the city’s finest. Croissants, tarts and apple galettes are an obvious (and wildly rewarding) choice; however, when seeking savoury satisfaction, the bakery’s deep-dish quiche does not disappoint. A wide selection of fresh-baked loaves – house sourdough, challah, brioche and oat walnut bread – should also be sampled copiously.

Rebuild Foundation

rebuild-foundation.org

Uncovering underused or wholly neglected spaces, restoring them using repurposed, often local materials and filling them with art, literature, film and theatre has proved for Rebuild Foundation a supremely successful urban regeneration strategy. Founder Theaster Gates, a Chicago native artist and urban planner known widely for highly effective and left-of-centre ideas regarding how to save community treasures from loss or destruction, envisions Chicago’s embattled fringes restored through a ‘culture based, artist led, and neighborhood driven’ approach.’ Enquire about tours of the Foundation’s spaces through its website.

Sandmeyer’s Bookstore

sandmeyersbookstore.com

Slip away from the bustle of the Loop and into the quiet, creaky-floored aisles of this husband-and-wife owned independent bookstore. Bibliophiles will recognise and appreciate the warm, enveloping aroma of paper pages teeming with stories – the unmistakable musk of all good bookstores cultivated over several decades. The store’s solid travel section is well worth exploring – linger and absorb its extraordinary ability to inject travel plans with romance unrivalled by electronic resources.

Trenchermen

trenchermen.com

Once a Turkish bathhouse, Trencherman’s striking interior delights almost as much as its food menu and highly commended cocktail list. And while the evening offering is well worth sampling, brunch should not be overlooked. Opt for pastries to complement locally roasted coffee (rotated monthly) as a prelude to dishes such as eggs florentine with buttermilk biscuits, kale and hot sauce hollandaise. If feeling a little dusty from night-before revelries, the list of brunch-appropriate alcoholic drinks serves as a standalone reason to stop by.

Underground Film Festival (CUFF)

Logan Theater

cuff.org

The Festival’s programme was perhaps best described by late American film critic Roger Ebert, as he articulated what set underground films apart from independents: ‘They exist on another plane – grottier, more anarchic, less eager to please, more willing to outrage.’ Visit in May for a three-day binge on unabashedly gritty, raw and curious cinema screened in the Chicago’s century-old Logan Theater (a stunning destination deserving of a visit regardless).

Volume Gallery

wvvolumes.com

Celebrating pieces that dance the line between functional object and conceptual art, Volume Gallery distinguishes itself with decidedly design-focused exhibitions. Fostering connections between makers and collectors, the event-oriented gallery’s collaborations and exhibitions pry open the scope of exposure for emerging designers. Should the idea of fitting your home with gallery-worthy furniture, many pieces straddling useful and ornamental are available for purchase.

Wrigley Field

chicago.cubs.mlb.com

Temple of Chicago’s fiery love of sports, Wrigley Field should be experienced by all visitors to the city – and in full flight where possible with beer and pretzels flowing abundantly. Home of the Cubs, the ballpark’s ivy-shrouded interior perimeter is what many call to mind at the mention of American baseball. And although it’s been more than a century since the beloved Cubs’ last World Series win, it’d be hard to guess from the electric atmosphere and the crowd’s fierce, unabating enthusiasm. Whipped up in the frenzy, wander and absorb the delights of surrounding Wrigleyville.

Xoco

rickbayless.com/restaurants/xoco

A swift and wallet-friendly feed packing heat, zest and simple fresh flavours. The eatery’s take on Mexican street food, namely its tortas (a classic Mexican sandwich served in supremely crunchy bread) sees tables full from early open to late close. Should eating on the go appeal, order the torta ahogada (juicy slow-roasted pork roaring with garlic, chilli salsa and marinated onion) head south on North Clark Street and wander along Chicago River.

Zolla/Lieberman Gallery

zollaliebermangallery.com

Celebrating its fortieth year in 2016, Zolla/Lieberman has played a pivotal part in defining and advancing Chicago’s contemporary art scene. The River North space is even credited with founding the bones of the surrounding gallery district. Across mixed media, painting, sculpture, metalwork and elaborate installations, the gallery’s programme, refreshed regularly, exhibits widely varied works by established and emerging artists.

Aesop Travel Guide: Chicago