2 .7 mil



distance from ORD airport to downtown


average summer temp


ideal travel time

4 days


ace hotel



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.


caffe streets



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.



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 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.


cellar door provisions

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.

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 and a make a stop at Plein Air Cafe afterwards.  

Area / Hyde Park

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

robie house.jpg

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.

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 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.


other recommendations


The Freehand  -  Hotel

Sawada Coffee  -  Cafe

Wicker Park  -  Neighbourhood

IIT Campus Architecture

Parachute  -  Restaurant

Lula Cafe  -  Restaurant

Doughnut Vault  -  Cafe

Longman & Eagle  -  Hotel

Millennium Park  -  Public Space

Logan Square  -  Neighbourhood