Blown away by the Windy City

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A long weekend is just enough to see some of Chicago’s stunning architecture, take a bite of fine cuisine and reconnect with old friends

With frequent and affordable air connections and lots to keep a person busy, Chicago is a great city to spend a three-day weekend. Whether it’s cheering on the Bears, Bulls or Blackhawks or oohing and ahhing over the sublime architecture, the Windy City has a friendly, laid-back vibe that will make you wish your stay was longer. But if 48 hours is all you’ve got, here are some tips to help you make the most of it.

Friday, 1 p.m.

Porter Airlines, which flies into Chicago’s Midway International Airport several times a day from Toronto, prides itself on being the only international carrier with flights in and out of the small airport, located about 13 kilometres southwest of downtown. That makes clearing customs a breeze and getting into the city by cab faster and cheaper than arriving at the larger O’Hare International Airport, which is about 27 kilometres northwest of downtown.

We check in to the mid-range Best Western River North Hotel, get our bearings and head for Michigan Avenue to do some shopping.

5:15 p.m.

After browsing the racks at J. Crew and Filene’s Basement — for which the phrase "bargain basement" was invented more than a century ago — we tuck into Hugo’s Frog Bar for a late-afternoon snack.

The servers are dressed in black ties and long white aprons and there’s a man playing jazz standards on an upright piano in the corner. Happy hour is drawing many in from the cool November air.

I order a smooth glass of Pinot Grigio and devour a delicious tilapia slider. The lightly breaded fish is tender and topped with a tangy tartar sauce. My companions and I also share an order of calamari and fries.

8 p.m.

After some less-than-savvy urban orienteering — in other words, I got us lost — we finally arrive at the Frontera Grill, a renowned Mexican restaurant owned by famed American chef Rick Bayliss.

The atmosphere is lively, the food looks great, but the joke is on us.

"It’s a two-and-a-half hour wait," the hostess says, batting her eyelashes with a weary expression that says: "You should know better."

I ask if we can make reservations for the next night, but it’s a no go. Our only option is showing up the next day at 4:30 p.m. — before the place even opens — and waiting in line to see if we can get in before the dinner rush.

Dejected, but no less hungry, we end up at Pizzeria Due, where the wait for a table is a far more reasonable 45 minutes. Chicago is famous for its deep-dish pizza and Due is one of the joints purportedly opened by the man who invented the gastronomic gut enlarger. The crust is thick and dry and I feel stuffed after just one piece.

11:15 p.m.

The Blue Chicago is a jazz and blues club around the corner from our hotel. When we arrive, Patricia Scott and the Mojo Mamas are working over the crowd, a mix of hipsters, thirtysomethings and grizzled old blues hounds.

During a break between sets, an ambulance pulls up out front. Paramedics clear a path to the stage and Scott is wheeled out on a stretcher, while the stunned audience awkwardly applauds.

Saturday, 12:25 p.m.

I’m in Chicago with three friends, all guys I went to university with a decade ago. One is a voracious sleeper, so it’s for his benefit that we are in this windowed bistro at the back of Fox and Obel, a high-end grocery store near the waterfront. Three of us have already had breakfast, but now it’s his turn.

Afterwards, we head to the Chicago River and take our seats on the 1 p.m. sailing of the Chicago Architecture Foundation’s boat tour.

Several people told me that if I do only one thing in Chicago, it should be this boat tour, and I gladly add my voice to the chorus. Susan, our guide, weaves an impressive narrative about many of the skyscrapers that border the river, including the shimmering 92-storey Trump Tower Chicago, the iconic Sears Tower (now called the Willis Tower) and my personal favourite, the Marina City buildings, which look like two corncobs reaching for the sky and are featured on the cover of alt-country band Wilco’s 2002 album, Yankee Foxtrot Hotel.

Susan also teaches us a phrase to describe modern buildings that borrow familiar touches from the 1920s: echo deco. We use it tirelessly for the rest of the day.

4:40 p.m.

I’m sitting near the marvellous marble grand staircase at the Art Institute of Chicago, catching my breath after scarfing down a meal of modern American, European and impressionist art. This is a tremendous collection and I regret not giving it the time and attention it deserves. A person could spend days here.

5:30 p.m.

We catch a cab to Revolution Brewing Company, north in Logan Park. The Lonely Planet guide says this is the neighbourhood where hipsters come when they can’t afford the rents in Wicker Park.

The bar/restaurant is a big open space with a beautiful tin ceiling and giant iron light fixtures with white glass globes inside.

Revolution makes 10 different flavours of beer on-site, including Iron Fist Pale Ale, Cross of Gold and Eugene, a rich, chocolate porter. In keeping with the name, the draft taps are all revolutionary-style clenched fists.

The menu features a wide selection of burgers, numerous vegetarian and vegan options and entrees, all under $25. Plus, Revolution isn’t listed in my Lonely Planet guide or any of the local guides, so we feel charmed to have found a place off the so-called beaten path.

Outside, I bum a cigarette from a hipster-looking guy with glasses and a beard.

"Half my family are from Halifax," he tells me. "Any Canadian is a friend of mine.".

Sunday, 12:44 a.m.

We take the El train’s blue line back into the city, planning to stop by the hotel to freshen up before heading out to catch some live music. It does not go as planned. Stuffed with beer and food and beat tired after a day of exploring, three of us fall asleep. Our 20-year-old selves would be disappointed in us.

8:45 a.m.

One of the guys and I don our running gear and zigzag east through the streets until we reach Lake Michigan shoreline. We head north on a wide cement landing, joining hundreds of other joggers and dog-walkers.

A few hours later, we join the crush of people trying to get a table at the popular brunch spot, Orange. Famous for its fruit sushi and orange-flavoured coffee, the fast and friendly service makes up for the long wait.

Satiated, we spend our remaining few hours shopping along the side streets off Michigan Avenue. While my companions grab a pint and catch the start of the Chicago Bears game — which, in an ironic twist, is being televised on this day live from Toronto where several NFL games are being played this season — I head into Bloomingdale’s Home. All weekend long, the unique character of this brown-brick building has caught my attention. Inside, there is opulence on every level — furniture, bedding, cookware, crystal, all of the finest quality. My Visa card is frothing at the mouth, though I can barely afford a set of coasters.

A blond woman at the cutlery counter tells me the store was once the Shriner’s Medinah Temple, that it housed a circus complete with elephants and guys driving those funny little cars and wearing tall hats. It was built around 1910, but bought by the retail company in the late 1990s and later transformed to the store it is today.

The tale reminds me of something fitting the boat tour guide said the day before.

"It is hopeless for the occasional visitor to try to keep up with Chicago — she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time."

Mark Twain wrote that in 1883. I can’t wait to prove him right.

Matthew Pearson is a reporter at the Citizen.

If You Go

Getting there: Chicago has two airports: Porter Airlines (flyporter.com) flies into the smaller Midway International Airport, which is southwest of downtown, while Air Canada (aircanada.com) and lots of U.S. carriers fly in and out of the much larger O’Hare International Airport, which is northwest of downtown.

Where to eat:

Hugo’s Frog Bar, 1024 North Rush St., hugosfrogbar.com

Frontera Grill, 445 N. Clark St., fronterakitchens.com

Pizzeria Due, 619 N. Wabash Ave., unos.com

Fox & Obel, 401 E. Illinois, fox-obel.com

Revolution Brewing Company, 2323 N. Milwaukee, revbrew.com

Orange, various locations, orangerestaurantschicago.com

Where to stay:

Best Western River North Hotel, 124 W. Ohio St., rivernorthhotel.com

More info:

Explore Chicago: The City of Chicago’s Official Tourism Site: explorechicago.org

Chicago Architecture Foundation (boat tours): architecture.org

Art Institute of Chicago: artic.edu

Organizations: Midway International Airport, O’Hare International Airport, Best Western River North Hotel J. Crew Chicago Architecture Foundation Sears Tower Art Institute of Chicago Revolution Brewing Company Chicago Bears Visa Air Canada

Geographic location: Chicago, Windy, Toronto Michigan Avenue Chicago River Marina Logan Park Halifax Lake Michigan U.S. North Rush

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