Explore walkable Chicago in 4 days

Sophisticated without the attitude


It’s not every day you follow a detoxifying, full-body mud wrap with a two-hour cupcake tour.

But this is Chicago, a foodie’s paradise, where over-indulgence can be excused by an active, outdoor lifestyle. And the walking.

So I sweat out about two pounds worth of toxins during my treatment at The Spa at Equinox. Then, I ingest about two pounds worth of cake, icing and pastry as we hit three cupcake shops and a Belgian bakery in just under two hours.

This is a good day.

But so are all the other action- and food-packed days I spend in the tall, friendly, beautifully built city. Chicago is one sexy place, and to quote expat Tina Fey—“I want to go to there.”

Look up. Look way, way up

Great idea—a river cruise with the Chicago Architecture Foundation. I take a seat on the open-top boat, staring skyward as the architecture eye candy glides by, one man-made wonder after another.

There is the Merchandise Mart, a two-city-block art deco wonder, and the Wrigley Building, inspired by Renaissance Europe. Here is the warehouse area, where factories were built facing away from the stench of the polluted river; many are now trendy condos, complete with large windows. (Great views aside, they still don’t recommend touching the Chicago River.)

Insider tip:

After the cruise, take a trip up the 110-storey Willis Tower (formerly the Sears Tower), where you’ll now be able to recognize the buildings as you gaze from the deck of one of the tallest buildings in the world. (Another frequently heard insider tip—head to the less-crowded John Hancock Observatory around sunset, and enjoy a drink at the bar.)

Shop ’til you drop

There is some serious shopping to be had in Chicago. And, much as I hate to waste precious hours of daylight inside a shopping mall, I simply have to see the three-storey American Girl store.

I head to the shopping mecca that is Michigan Avenue. The guidebooks call it The Magnificent Mile, and for good reason. There are high-end boutiques, big-name chain stores such as Macy’s, Bloomingdale’s and Nordstrom, and a stream of trendy cafes.

Insider tip:

Locals don’t call it The Magnificent Mile. In the unpretentious way of Chicagoans, it is simply Michigan Ave.

Park it

370 Crown Fountain in Millennium Park.

If you want to cover a lot of ground, and pick up some history, try a Segway tour of Grant and Millennium parks. Our guide leads us, like a row of ducklings, through the parks and an explanation of the Great Chicago Fire of 1871. It razed the downtown, leaving the city with a blank slate. This is why there is a 42-kilometre-long waterfront in Chicago with no industrial blight or pricy condos hogging the views from the good citizens of the city. Chicagoans love to stroll the pathways, taking in the lake, the diverse skyscrapers—Art Deco, Gothic, modern steel and glass—and the live outdoor music that is a staple of summer here.

The parks, and adjoining Museum Campus, house several of the city’s top attractions including The Art Institute of Chicago, the Field Museum and Shedd Aquarium, all of which are worth an afternoon.

Insider tip:

Fireworks at Navy Pier all summer. A good vantage point is the Rebar lounge in the Trump building; drinks are pricy, but the sushi and the views are second-to-none.

The Windy City

Chicago is windy. I know they insist the nickname doesn’t come from the wind, but from a dispute between bombastic politicians before the World’s Columbian Exposition in 1893, but the fact remains: this city is just crazy, knock-tourists-off-their-Segways windy.

Maybe that’s just because I visited during a rainy week, but the “refreshing breeze” off the lake that the literature likes to mention—that’s code for “bring a windbreaker.”

So I don’t know what to tell you about the weather. Oh, yes I do—dress in layers.

Inside the Actor’s Studio

Did I mention it is windy on the day of our Segway tour? So windy, our group huddles together in the tour office after handing over our helmets. That’s how I discover that most of the Absolutely Segway guides are actors.

The reason this seems weirdly serendipitous, is I have just seen the Second City show the previous night—100th Revue: Who Do We Think We Are?—and am still laughing. I want to know more about the people who create the theatre and comedy scene here.

Chicago is known for live comedy and great theatre. You can take in everything from a Broadway show (Rock of Ages and RAIN: A Tribute to the Beatles) to Second City, the training ground of Steve Carrell, Tina Fey, Stephen Colbert and, maybe, your Segway tour guide.

Or you can just wait for your waitress to slip you the playbill for the musical she’s directing, which starts at 11 p.m. should you be interested, and is only a 10-minute cab ride away. If this happens, you must go. Especially if it is a musical based on the movie Bill & Ted’s Excellent Adventure.

Insider tip:

To rub shoulders with the actors from Second City, post-performance, go to the Old Town Ale House for cheap beer and good jazz. Warning: Cash only, and it’s a bit of a dive.

Another night, check out The Redhead Piano Bar, with its versatile, request-taking musicians and an extensive martini list. This is where we discovered that bars in Chicago stay open until— ahem —5 a.m. So go ahead, order the watermelon martini and request a Billy Joel song (write it on a napkin, and add a nice cash tip).

Do not schedule an early morning architecture cruise after an evening at The Redhead Piano Bar.

From Art Galleries to Hot Dogs


There is high art, like the original, 1930 American Gothic painting by Grant Wood (you know, the couple with the pitchfork) in the Art Institute of Chicago. And there is high-end cuisine, like the stellar meal we enjoyed at The Bedford, a foodie paradise set in the vault of a landmark bank. Like New York, you could spend days immersed in highbrow culture and entertainment.

But you really shouldn’t miss out on the everyday Chicago pleasures, like deep-dish pizza and the Chicago-style hot dog. The best place to eat one of these water-simmered, all-beef delicacies—bar none—is at a Chicago Cubs game at Wrigley Field, on a sunny day.

Insider tip:

Go to Chicago. Be prepared to eat, drink, shop, walk, laugh and love this place.

It’s a Midwestern Thing

How could a place with this much culture and history also feel so laid-back, safe and just plain friendly? And then my new friend Allie Galecki, a lifelong Chicagoan, spells it out. Chicago, she says, is sophisticated without the attitude. This makes sense. I had several exchanges that went something like this:


Chicagoan: “You notice people are friendly here?”

Me: “Yes!”

Chicagoan: It’s a Midwestern thing. You been to New York?”

Me: “Yes!”

Chicagoan: “Well, then.”

WestJet Banner