The Windy City is one of our most adored destinations for all things food and architecture. Whether you define it by its urban feats of being a city built on water, being 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 friendliest cities we've ever had the pleasure to visit, it is filled with confident and imaginative cooking, diverse inspirations, and pocketed neighbourhoods making it as unique as ever. Chicago is a big city metropolis at its finest, while still having an inviting small-town local culture that makes you feel right at home.
2 .7 mil
distance from ORD airport to downtown
average summer temp
ideal travel time
The always-promising ACE Hotel located in the West Loop neighbourhood is the perfect place to call home. 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-buzzing restaurant scene, which is sure to not disappoint.
Area / West Loop
Vibe / Laid-back minimal cool, but with rough-around-the-edges details and guitars in your room.
This local neighbourhood gem is warm, inviting and serves no frills great coffee and excellent scones. An environment suited for a quick catch-up with friends, needing to get some work done, or people-watching out of the expansive windows all within a wonderfully designed space that defines Chicago hospitality at its best.
Area / Wicker Park
Vibe / A warm cavern for respite, with locals making you feel right at home.
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 Chicago urban environment wonderfully, all while profiling the city's 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 the time to wander around the Fulton Market District which once housed much of the wholesale produce distribution and lumber factories in the 19th century, you will notice one thing that stands out: there is a pungent smell of chocolate that lingers in the air. You look around trying to find out where that smell is coming from, but can't quite find 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.
Area / Fulton Market
Vibe / Warehouse cool with cobblestone streets and a buzzing restaurant scene.
Bakery and Cafe
On a neighbourhood street corner with a bright and sunny storefront, some of the best pastries and baked goods are being crafted with the utmost love and care. A strip of brown paper houses the daily handwritten menu for breakfast or lunch, from naturally-fermented sourdough and custardy quiches to pillowy ricotta gnudi and turnip hummus with dukkah. 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.
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 and a 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 stunning 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 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 but completely relevant to the city's food culture. A well-priced and highly suggested 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.
One of Paul Kahan's most notable spots amidst his Chicago restaurant collection, Avec revolutionized the eating culture of the city with a family style dining experience focusing on Mediterranean plates that begged to be shared. What was originally conceived as a wine bar has evolved into its rightful place as one of the most coveted restaurants in Chicago, equally as enjoyable for lunch as it is for dinner. In particular, their chorizo-stuffed medjool dates are a must to kick off your meal.
Area / Fulton Market
Vibe / Clean and contemporary in a small intimate space, with all the characteristics of your favourite diner.
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 up-and-coming Wicker Park. 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 grab a coffee at Cafe Robey, be sure to make this your destination. Oh, and did we mention the rooftop pool with 180-degree views?
Area / Wicker Park
Vibe / Danish design cool in a local hood, housed within quintessential Chicago architecture.