Chicago City Guide

Chicago City Guide

Chicago is the kind of city that feels young but really isn’t. The Midwestern capital cultivated the rise of modern architecture in the U.S., possesses one of the world’s largest art collections, and within the last two decades has garnered a global reputation for culinary innovation. Chicago thus provides the ideal city break for the modern cultural traveller. From strolls along the Victorian mansion-lined streets of Wicker Park to evenings spent at the West Loop’s au courant cocktail bars, the city seamlessly merges the old with the new.

This guide reflects a 3-day stay in Chicago. Therefore, the guide does not aim to be comprehensive but strives to be a well-curated work in progress. Generally speaking, the city’s best neighbourhoods were Fulton Market District, Wicker Park, Logan Square and Hyde Park as they housed the highest concentrations of creative people and spaces.

ACE HOTEL / Boutique Hotel / Fulton Market District

Located in one of Chicago’s hippest and foodiest neighbourhoods, the newly built Ace Hotel is sure to please any young urban sophisticate. The boutique hotel, built by GREC Architects, pays homage to the Bauhaus school and reflects on Chicago’s heritage as an architectural mecca. The rooms exude a modern industrial feel with towering concrete walls and ceilings juxtaposed against retro-inspired furniture. The hotel also has a splendid rooftop bar, known as The Waydown, which boasts incredible views of the Loop and an impressive cocktail menu – qualities that have made it a popular evening destination for the creative set.

AU CHEVAL / Restaurant / Fulton Market District

One can be guaranteed to have a memorable experience at this trendy upscale American diner. For one, the chefs are known to cook up the best burgers in town. I can personally speak to the fact that their traditional burger (with thick cut peppered bacon) ranks among the top three burgers I’ve ever tasted! Simply put, the hype surrounding Au Cheval is well deserved. Furthermore, the restaurant’s dark leather booths and dark wood panelling create an aura that is as seductive as its elevated diner dishes.

ART INSTITUTE OF CHICAGO / Museum / Millennium Park

Known as the second largest art museum in the U.S. (behind The Met) the art institute of Chicago is sure to please art-lovers of diverse aesthetic sensibilities. I would recommend starting off with a viewing of Anish Kapoor’s Cloud Gate (2006). Although the sculpture can easily be written off as a basic tourist attraction, I implore visitors to see it as phenomenal work of public art: one that that merges the familiar with the unfamiliar by reflecting its immediate urban surroundings while also emanating a mysterious unearthly aura. Within the actual museum, I would recommend a stroll through its impressive permanent collection – favourites including Edward Hopper’s Nighthawks (1942) and three of Constantin Brancusi’s stunning sculptures.

DOVE'S LUCHEONETTE / Restaurant / Wicker Park

Situated in the heart of Wicker Park, this neighbourhood favourite has gained a reputation for its hearty Southern-inspired Mexican cuisine. The space is small and cosy with a humble interior that references the glory days of the American diner. Most dishes are worthy of selection but the “Chicken Fried Chicken” and the “Burnt End Hash” have become crowd favourites.

GATHER HOME & LIFESTYLE / Lifestyle store / Wicker Park

Gather is a modern lifestyle store that offers a selection of minimally styled home products ranging from design publications and apothecary products to plants and jewellery. The store is dedicated to simplifying the lives of its clientele while introducing them to a wide array of independent creators.


Right next to a bustling train station exists this calm oasis where visitors can work, converse and relax. The airy space is designed with an unapologetic modern sensibility with its textured concrete pillars and mid-century inspired chairs. A laid-back café by day and a lively cocktail bar by night, The Lounge is a testament to the beauty of multi-functional spaces. The Robey Chicago is also another excellent hotel choice for those in search of a small-scale, design-conscious experience.


Cruises are usually frowned down upon as tourist traps but one has to make an exception when visiting Chicago. Given the central role that Chicago has played in fostering the rise of modern architecture, from Franklin Lloyd’s earlier innovations to Mies Van der Rohe’s International Style, a tour of the city’s historic skyline is not to be missed. Chicago’s First Lady Cruises, one company among many, is known for offering informative, accessible tours at many hours of the day.

Additional Recommendations:

PUBLICAN / Restaurant / Fulton Market District

DOUGHNUT VAULT / Bakery / River North

GIRL & THE GOAT / Restaurant / Fulton Market District

LULA CAFÉ / Restaurant / Logan Square

MOMOTARO / Restaurant / Fulton Market District

THE ROBIE HOUSE / Architectural Sight / Hyde Park

RSVP GALLERY / Fashion & Lifestyle Store / Wicker Park