The Windy City is one of the most adored destinations for all things food and architecture. Whether you define it by its urban feats of being built on water and then rebuilt again with even bigger and taller steel buildings after a great fire, or a place where restaurant and art culture is constantly shifting and emerging, it is a city with big thinkers who make things happen. Aside from the fact that it is one of the utmost friendliest cities, it is filled with confident and imaginative cooking, diverse and inspired people, and unique pocketed neighbourhoods. Chicago is a big city metropolis at its finest, while still having an inviting small-town social culture that makes you feel right at home.


2 .7 mil



distance from ORD airport to downtown


average summer temp


ideal travel time

4 days

ace hotel



The always-promising ACE Hotel debuts in the West Loop neighbourhood as a tranquil retreat in an otherwise buzzing area. With an array of different room sizes each housing different artwork by local art students, you will be comfortably situated amongst the central and always riveting restaurant scene, which is sure to not disappoint. Be sure to stay in one morning and enjoy breakfast at City Mouse, helmed by hometown Chicago chefs from Giant reasturant in Logan Square.

Area / West Loop

Vibe / Laid-back minimal cool, but with rough-around-the-edges details and guitars in your room.


caffe streets



This local neighbourhood gem is warm, inviting and serves no frills great coffee and excellent scones. An environment equally suited for a quick catch-up with friends or hanging solo and people-watching out of the expansive windows with a book in hand; the cavernous, intimately designed space and the people behind the bar define Chicago hospitality at its best. 

Area / Wicker Park

Vibe / A warm cavern for respite, with locals making you feel right at home.


Public Space


It's not often that you can hang out in a central public space that winds right through the centre of the city. Whether grabbing some lunch and watching the boats drift by along the river, renting a kayak or bicycle to explore the linear urban park, or taking a walk at dusk and admiring the collection of stunning urban Chicago architecture that surrounds it, the Riverwalk summarizes the city's urban environment wonderfully, all while profiling the magnificent success of being built on water.

Area / Downtown

Vibe / The city's public living room, stretched along an urban river.

fulton market district



If you have time to wander around this district which once housed much of the wholesale produce distribution and lumber factories in the 19th century, you may notice one thing: there is an aromatic smell of chocolate that lingers in the air. You look around trying to find the origin of the intoxicating scent, but can't quite put your finger on it. Don't be alarmed, the Blommer Chocolate Company is the culprit. Let this chocolate smell be the segway to one of the most dynamic and interesting neighbourhoods to eat in Chicago. Whether it's Monteverde for excellent pastas, or Roister for inventive wood-fired dishes, you've got all choices at your fingertips here.

Area / Fulton Market

Vibe / Warehouse cool with cobblestone streets and a buzzing restaurant scene.

cellar door provisions

Bakery and Cafe


On a neighbourhood street corner with a bright and sunny storefront, some of Chicago's best pastries and baked goods are being crafted with the utmost love and care. A strip of brown paper houses the daily handwritten menu, from naturally-fermented sourdough and custardy quiches for breakfast to pillowy ricotta gnudi and turnip hummus with dukkah for lunch. A slow Saturday morning with a flaky croissant and a chat with some friendly neighbourhood locals is a slice of heaven.

Area / Logan Square

Vibe / Scrappy casual yet perfectly tidy, with an open kitchen emitting the most wonderful scents.

robie house



Part of a collection of houses that Frank Lloyd Wright designed in Chicago, the Robie House defined the New American Prairie Style at its finest. Completed in 1910, the house's horizontal roof lines, deep overhanging eaves, and natural materials encapsulated the context of the American Midwest and began a precedent for residential architecture in Chicago. A trek to the house is worth it to tour the tree-lined neighbourhood, but be sure to make a stop at Plein Air Cafe afterwards.  

Area / Hyde Park

Vibe / Prairie House Americana with exquisite details to admire for hours.

art institute of chicago



If you ever had a fantasy to pull your own Ferris Bueller's day off, this is the exact place to bring that dream to fruition. This museum is a Chicago staple cherished by visitors and locals alike. Linked adjacently by a pedestrian bridge to Millennium Park, which makes for a lovely outdoor space for post-art contemplation, enjoy beautiful artworks from Van Gogh, Monet and Degas to name a few. With an impressively detailed addition designed by architect Renzo Piano, you'll easily get lost in both the art and the architecture. 

Area / Millenium Park

Vibe / A welcome retreat from the city, with contemporary spaces and old courtyards to immerse yourself in.




For some of the most exciting New American cooking in Chicago, this minimal restaurant by husband-and-wife team David and Anna Posey fits the bill. Both Chicago alum of some of the finer eating establishments in the city, the two have created a place which feels warm and charming yet incredibly relevant to the city's wide-reaching food culture. A well-priced and highly recommended tasting menu will end with one of Anna's signature desserts which is just as much a treat to look at as it is to eat. 

Area / West Loop

Vibe / Minimal Scandinavian design, with personal charm and a lovely courtyard.




Paul Kahan is a name synonymous with excellent cooking in Chicago. One of his most notable spots amidst his restaurant endeavours, Avec, revolutionized the eating culture of the city with a family style dining experience focusing on Mediterranean plates that are begging to be shared. What was originally conceived as a wine bar, has quickly evolved into its rightful place as one of the most coveted restaurants in Chicago, equally as enjoyable for lunch as it is for dinner. Any dish will be a standout and a mesmerizing affair, but be sure to kick off your meal with the intensely delicious chorizo-stuffed medjool dates.

Area / Fulton Market

Vibe / Clean and contemporary in a small intimate space, with all the characteristics of your favourite diner.

the robey


For a place to rest your head that feels uniquely Chicago while also being a retreat from the centre of the city, the Robey is the hip boutique hotel of the vibrant Wicker Park neighbourhood. Housed in an Art-Deco tower originally built in 1929, the 29-storey building was the first Chicago skyscraper to be built outside of the Loop. Whether you are in town on business, a Chicago native looking for a stay-cation, or just looking to pop in and grab a coffee at Cafe Robey, this understated and minimal space serves as the perfect retreat. Not to mention the surreal rooftop pool with 180-degree views of the city. 

Area / Wicker Park

Vibe / Danish design cool in a local neighbourhood, housed in quintessential Chicago architecture.


other recommendations


The Freehand  -  Hotel

Sawada Coffee  -  Cafe

Wicker Park  -  Neighbourhood

IIT Campus Architecture

Parachute  -  Restaurant

Lula Cafe  -  Restaurant

Doughnut Vault  -  Doughnut & Coffee Shop

Longman & Eagle  -  Hotel

Millennium Park  -  Public Space

Logan Square  -  Neighbourhood