Jazz clubs, glittery skyscrapers, and architectural monuments to rival that of New York's — Chicago is one city that never sleeps. While the Chicago of old was a major player in the shipping industry, the city today is decidedly cosmopolitan. Everyone has their own A-list spots of the city and I'm happy to share some of mine.

Heritage Bicycle General Store

Heritage Bicycles General Store
2959 North Lincoln Avenue

If you love to cycle around the city, be sure to drop by the Heritage Bicycles General Store at Chicago's Lakeview neighborhood. Their gorgeous handcrafted bikes are proudly made in Chicago and sport classic designs that throwback to an earlier time in Chicago's history. There's a cute coffee shop within, too, that's perfect for a mid-afternoon break.  

RL Restaurant

RL Restaurant
115 East Chicago Avenue

The legendary RL Restaurant has been hosting the society's crème de la creme for close to two decades — long before the Polo Bar by Ralph Lauren opened in midtown Manhattan. This is the perfect place for lunch before you hit the Magnificent Mile for a spot of shopping.

Doughnut vault

Doughnut Vault
401 North Franklin Street

No visit to Chicago would be complete without slipping over to the Doughnut Vault. Get there quickly. It opens at 9am but the line starts even before that and the store closes the moment they run out of their sweet treats. Flavours range from the classic red velvet to peanut butter cream.

15 East Huron Street

Sited within walking distance from The Peninsula Chicago, this store features a unique mix of hand-selected fashion labels from America, Europe and Japan. On the service side, their attention to styling is unparalleled. 

The Second City

The Second City
1608 N Wells Street

What began as a small cabaret theatre in 1959 has grown to be one of the most influential comedy theatres in the world. Steve Carrell and Tina Fey were spouting lines here even before they became household names. Get ready to laugh out loud at one of their shows — the theatre is a living institution in Chicago.