Chicago From A New Angle

By Michael Macaulay

Let the Windy City breezes take you out of The Loop into fresh areas like Andersonville and Pilsen. Chicago has great neighbourhoods to wander through and to get different tastes of the city. On your next visit, mix it up with these suggestions on tested and true places for you to enjoy.

Expansive glass wall facing the river in Chicago and bridge lined with American flags.


5219 North Clark Street

Brimfield just brims with fun, offering many vintage items from all the states in the USA, as well as from Canada (60’s felt pennants from Ontario cottage country!). There’s a lot to explore, including the lower level, and it’s organized in themed areas to help you keep track, and find even more treasures to buy for your friends (i.e. yourself). Owner Julie Fernstrom sure knows how to stock her store for you!

A wooden table of assorted merchandise, and a wall poster of cartoon ranger bears  as the focal point.

Cowboys and Astronauts

1478 W Summerdale Ave

Yes, there is a life-size astronaut model in the store – just because. There’s also a carefully chosen range of clothing and home goods to outfit both you and your household. Owners Matthew and Greg give you a warm welcome, and will help you find just what you need and sometimes even items that you didn’t know you needed. 


1475 W Balmoral Avenue

This is definitely a neighbourhood favourite, where you’ll see locals returning again and again. The menu is American, with French je ne sai quoi – clearly an essential ingredient in their frites!  The warm service helps you feel like a local, and they’ve got helpful suggestions to ensure your meal is relaxed and happy.

Front street entrance of Vincent restaurant with a yellow sign and interior of the bar counter.

The Office

955 W Fulton Market

With just 18 seats, and tucked under The Aviary, this is a secret destination. You feel like you’re at a private club, with low lights and a truly amazing range of rare spirits from 1807 to 2019. Reserve the Office Hour for two cocktails and some small plates, to start or end your evening. The team will guide through the selections, and help you feel like a VIP member.


1239 W 18th Street

The Pilsen neighbourhood of Chicago bursts with cool places to eat and drink. And S.K.Y. is one of the best. Is this restaurant’s menu Asian-American? Or American-Asian? It’s definitely Tasty-Tasty. The food menu changes monthly to reflect Chef Stephen Gillander’s imagination and tastes, and the drinks menu keeps pace with its own stirring evolutions.