Notable Destination: Chicago

Like any big city, Chicago is best experienced by visiting the diverse districts and neighbourhoods that make it unique. I had three days in May to do just that, and thankfully was able to coordinate this trip with a very good friend, and intrepid foodie, Ivy Ackerman. Her company – Butter And Egg Road – seeks out the best of the best dining experiences for its members, and combines these with cultural happenings. The results are weekend programs in major cities that allow visitors to get an inside scoop on the local scene. Toronto and NYC are already going strong, while Montreal and Chicago are launching soon. And since Ivy had to do some research on the latter, I need not say I was in good company.

Homebase: PUBLIC (pictured above)

Being of the age where a dirt cheap hostel won’t do, but of the means to keep my eye on mid-range hotels, I’m always quick to offer up suggestions when I find a special place. Ian Schrager’s latest venture – PUBLIC – gave me luxe for less and it is my new favourite home away from home.

Once all checked in, and after regrouping over lunch at the famed Pump Room, our first stop was the WEST LOOP.

Formerly filled with factories and wholesale warehouses, in relatively short order the West Loop has flipped over to a desirable district for living, eating and shopping. Boutiques like Fix outfit both men and women in designer duds, while the Packer Schopf Gallery offers to outfit walls with the fresh work of emerging artists.

Morlen Sinoway provides a covetable mix of home wares, modern art pieces, and statement-making jewellery.

Aside from one of the world’s most acclaimed foodie destinations (Next Restaurant, anyone?), there are classic diners and very worthy brunch spots. The Publican and Girl & The Goat are two standouts.

Cocktails at The Aviary  are pure genius, and I mean that quite literally. The state-of-the-art drink kitchen is a molecular science lab. Reservations operate on a lottery system, whereby one must email day of, and they will confirm or deny entry at 4pm. Ivy charmed our way in, but some will wait months at a time. Worth it? Absolutely!



This is, hands-down, Chicago’s up-and-coming hood. Gentrification is sustaining cool shops and even cooler restos that dot the area’s historic boulevards.

Saturday. Brunch. Two great words, that taste even better when one find places like Longman & Eagle (pictured below). We started by sharing a made-from-scratch maple and fig doughnut that was seemingly some sort of cosmic gift (more on this on My Duck Hash made for one of the best breakfasts I’ve ever had.

On the other side of a grassy intersection, there is another popular spot for brunch, lunch or dinner, Lula Cafe, with an eclectic and bright atmosphere that is the polar opposite of L&E’s pub-like appeal.

La Boulangerie brings a slice of Paris to the Midwest. The smell of fresh baked baguettes, and other pastries that only the French do best, is worth the visit.

Also, stirring up a ton of buzz is Telegraph. This wine bar has been named as one of North America’s best ( 2013), with Jeremy Quinn singled out as one of the country’s top sommeliers (Food & Wine 2012). A must if you like the vino.


The Magnificent Mile doesn’t look all that once you’ve shopped this strip. North Damen is lined with amazing boutiques.

Starting at the northern end of North Damen, we loved Roslyn (pictured, middle photo, left)for local and international designer clothing, as well as gorgeous jewellery. The boutique is well known for all things bridal party. Walking towards Wicker Park, The Edit is a stylish stop (we made two trips!) for the ladies, and then Apartment Number 9 does a solid for the dudes who can appreciate labels like Band of Outsiders and Fred Perry. A little further on and we found a stunning Marc Jacobs store. I picked up a sweet iPad case ($65) here, but you can shop items from $3 to $3000.

I could not get enough of the fantastic jewellery on display at Riley and Love And Pieces. Much of it by local artists, and very well priced.


We kept caffeinated for our shopping and exploring at BUZZ: Killer Espresso (pictured, middle photo, centre), one of those places you could sit and work at, or people watch, for hours.

Don’t need to say much more about Lillie’s Q than it is clear why the restaurant was rated best BBQ in US by Food & Wine magazine. Go for the great beers, and don’t forget to order the Shrimp & Grits (pictured top).

Does it get any better that tacos and tequila on a big bright patio? Big Star is close to all the aforementioned shops and is absolute perfection on a sunny day. Open for dinner, lunch and late-night bites.

Not too far away, in the Avondale hood, is Kuma’s Corner. The only way to describe it is biker meets burger bar. And the latter is what packs the joint with all types…just don’t ask management to turn the music down.

Other Notables:

– The Architecture Boat Tours came on the good word of more that one trusted traveler. Along the Chicago River route, entertaining guides tell the dramatic story of the Great Fire, and how the city became the birthplace of modern American Architecture.

– Agent Provocateur is one retailer that we will likely never see on Canadian soil. Stock up on sexy at 47 East Oak Street.

– space 519 at The Shops at 900. Ivy scoped out this “refined general store” that carries everything from expertly curated gifts and books, to aesop and RGB nail polish.

Two Ways To Save:

– It is easy to get around the city, and to it from O’Hare via the CTA system. For the sake of time, I do suggest taxis to some districts, and always late at night. Otherwise, public transit is cheap and reliable.

– Don’t think you have to go out and buy new clothes for a trip to Chi-Town. Fashion is decidedly dressed-down. You’re all good with jeans and trendy tops and t-shirts.