The Windy City has always been one of our favourite eating destinations. With its mix of confident cooking, brazen portions, diverse inspirations, and great local ingredients (not to mention the fact that everyone is so friendly—and so into food), it’s where you go for a big, fat weekend, or tack on an extra day to your business trip to squeeze in a few more reservations. (Did we mention the drinking’s top-notch, too?) Definitely our kind of town.

 

population

2 .7 mil

currency

USD

distance from ORD airport to downtown

27km

average summer temp

77F

ideal travel time

4 days


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ace hotel

Hotel

 

The trendy ACE Hotel located in the West Loop neighbourhood is the perfect place to call home while you're in Chicago. With an array of different room sizes to suit any budget, you will be comfortably situated amongst the central and always-buzzing restaurant scene, which is sure to not disappoint.

311 N Morgan Street / Chicago, IL / 60607

 

caffe streets

Cafe

 

This Wicker Park gem is warm, inviting and serves great coffee. Anyone who wants to get social with friends, needs to get some work done, or who wants to admire the contemporary architecture, would enjoy all of this and more at Caffe Streets. 

1750 W Division Street / Chicago, IL / 60622

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riverwalk

Public Space

 

Immerse yourself in Chicago's central public space. Have a picnic along the river, rent a kayak or a DIVVY bike to explore the Riverwalk and enjoy being outside. A walk along the water in the summer will allow you to take in all of the Chicago architecture, catch a live music performance or cool art installations. There is always something happening on the Chicago Riverwalk.

fulton market district

Neighbourhood

 

If you have the time to wander around the Fulton Market District, 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.

 

Washington Boulevard to Grand Avenue / I/90-94 west to Ogden Avenue

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cellar door provisions

Bakery and Cafe

 

Some of the best pastries can be found here. Located in the hip Logan Square neighbourhood, grab breakfast Wednesday through Sunday or make a reservation for dinner either Friday or Saturday.  This is the perfect destination for a slow Saturday morning with friends. Also, their croissants are legen...wait for it.

 

3025 W Diversey Avenue / Chicago, IL / 60647

robie house

Architecture

 

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5757 S Woodlawn Ave

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art institute of chicago

Museum

 

If you ever had a fantasy to pull your own Ferris Bueller's day off, this is the exact place to channel that dream. This museum is a Chicago staple and should not be missed. Located adjacent to Millennium Park and the famous "Bean" or properly named, Cloud Gate, enjoy beautiful artworks from Van Gogh, Monet and Degas to name a few. Designed by starchitect Renzo Piano, you'll easily get lost in both the art and the architecture. 

 

111 S Michigan Avenue / Chicago, IL / 60603

elske

Restaurant

 

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311 N Morgan St, Chicago, IL 60607

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avec

Restaurant

 

One of Paul Kahan's most notable spots amidst his Chicago restaurant empire, Avec is a family style dining experience with a focus on Mediterranean plates that begged to be shared amongst your nearest and dearest. What was originally conceived as a wine bar, has evolved into one of the most coveted reservations in the West Loop. In particular, their chorizo-stuffed medjool dates are a must to kick off your meal.

 

615 W. Randolph / Chicago, IL / 60661

the robey

Hotel

What was formerly known as the Hollander Hotel, the newly renamed Robey is the hip boutique hotel of Wicker Park. The art-deco north west tower, originally built in 1929, 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? 

2018 West North Avenue / Chicago, IL / 60647

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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