Friday

2 p.m.

Air Canada can get you straight to O’Hare from just about anywhere in the country. By 2 p.m., we had cleared customs, grabbed a cab and checked into The Hotel Felix (111 West Huron St.), a boutique hotel ($272 a night) about four blocks from Michigan Avenue’s shopping mecca, the Magnificent Mile.

3 p.m.

In warmer weather, get your bearings on a Chicago Architecture Foundation river cruise. This 90-minute trip up the Chicago River is the best way to take in some of the stunning architecture for which this city is known. An expert CAF docent will tell you about more than 50 buildings, among them those two former contenders for world’s tallest building: the Trump Tower, the Sears Tower (now called the Willis Tower), as well as Mies van der Rohe’s minimalist Wabash building and the postmodern Aqua with its wavy balconies. Cruises cost $32 a person and leave from Riverside Gardens just under the Michigan Avenue Bridge at Wacker Drive.

5 p.m.

Enjoy high tea (or cocktails) in the legendary Drake Hotel’s (140 East Walton Pl.) Palm Court with its gorgeous Italian Renaissance design and harpist. Since it opened in the 1920s, The Drake has hosted the likes of Judy Garland and Winston Churchill. Marilyn Monroe and Joe DiMaggio carved their initials in the wooden bar of the Cape Cod Room.

7 p.m.

You can endure the two-margarita wait to get into one of Rick Bayless’s renowned high-end Mexican restos (Frontera Grill and Topolobampo) or you can make a reservation at the equally excellent Salpicon (1252 North Wells St.), where chef Priscilla Satkoff serves up tiny perfect tamales filled with black beans, Chihuahua cheese and spicy mocajete salsa. Her moles are to die for and the bar stocks more than 100 tequilas. Ole!

Saturday

8 a.m.

Whet your appetite for breakfast at Green City Market in Lincoln Park. Stroll around and feast your eyes on the cornucopia of fruits, veggies, baked goods and cheeses before tucking into one of Zullo’s egg focaccia sandwiches and an apple cider doughnut . . . or two.

11 a.m.

Get a high-culture fix at the Museum of Contemporary Art. There is no permanent collection, so you’re at the mercy of the scheduling, but the exhibitions are first-rate. We enjoyed a spirit-lifting showing of Alex Calder’s joyous mobiles and sculptures. The fish-shaped staircase is also worth a look.

1 p.m.

While you’re there, grab lunch at Puck’s at the MCA. The clean, minimalist room overlooks the museum’s sculpture garden and Lake Michigan in the distance. The menu changes daily; his sandwiches are always stellar. Our favourite: wiener schnitzel on grilled sourdough.

2 p.m.

Neiman Marcus, Macy’s, Saks Fifth Avenue, Nordstroms: They’re all there on Michigan Avenue’s Magnificent Mile. Spend an afternoon browsing or go ahead and blow the budget. Great gifts can be found at the Chicago Architecture Foundation Shop (224 South Michigan Ave.). Or take home a tub of Garrett Popcorn’s Chicago Mix (cheese and caramel). Sounds gross but it’s totally addictive.

5 p.m.

The cafe on the 94th floor of the John Hancock Centre is known for its innovative specialty coffees. If the weather is blustery, feel the building sway as you take in the spectacular views while warming yourself with a Tia Maria-laced espresso.

7:30 p.m.

Originally a shelter for ice skaters, North Pond restaurant is easily the most romantic dinner setting in the city. It’s located in Lincoln Park overlooking a pond that in turn overlooks the dramatic city skyline. Chef Bruce Sherman’s tasting menu ($85 per person) is a brilliant riff on the SLO (seasonal, local, organic) food trend sweeping North America.

Sunday

9 a.m.

Ride the L (Pink Line) out to Pilsen, the Mexican neighbourhood on Chicago’s Lower West Side. After a breakfast of huevos rancheros and refried beans at Nuevo Leon (1515 West 18th St.), take a walk by the colourful street murals.

11 a.m.

Head back downtown and work off breakfast with a stroll through Millennium Park. Anish Kapoor’s Cloud Gate, a 110-ton stainless-steel “bean” is one of the world’s most compelling pieces of public art. A concert pavilion by Frank Gehry, the Lurie Gardens and the Art Institute of Chicago yield hours of fascination.

2 p.m.

Yes, you’re full, but you really should sample the city’s signature deep-dish pizza (they’re so huge you can take the leftovers back to your hotel for dinner). We stopped at Gino’s East, a graffiti-strewn emporium at 633 North Wells St., just around the corner from our hotel.

3 p.m.

Baseball fans will want to catch a game at Wrigley Park, but be sure to reserve tickets well in advance. Architecture buffs won’t want to miss the bus tour of Oak Park (visitoakpark.com) to see homes designed by Frank Lloyd Wright.