The floor-to-ceiling windows in the bustling bar reveal heart-stopping views of the city, which attract in equal measure camera-happy tourists and Chicagoans celebrating special occasions.
Drinks are pricey, just under $22 for most cocktails, which is what it costs to ascend to the Sears Tower's observation deck.
Would you rather spend $22 for a view, or $22 for a view plus a cocktail? I rest my case.
Chicago has been getting a lot of attention these days. As I mentioned, the city provided the man who tomorrow will be inaugurated as President. The state governor was indicted for trying to sell Barack Obama's old Senate seat. (Since political corruption is as much a Chicago tradition as eating hot dogs with mustard instead of ketchup, most people consider this high entertainment.)
The city is also the front-runner for the 2016 Olympic Games.
There are some great places here, such as Wrigley Field, the Art Institute and the Field Museum. The Art Institute mounts world-class exhibitions and contains a unique collection of doll's house furniture.
The Field Museum owns the original of skeleton of Sue, the largest and best-preserved Tyrannosaurus Rex ever discovered, a replica of whom is now at Auckland Museum.
The ivy-covered beauty of Wrigley Field, one of the most famous baseball parks in the US, guarantees Cubs' games sell out despite a solid century without a World Series title.
But I'm going to assume you know about these places because if you're planning a trip to Chicago, your guidebook will gush about these attractions, and rightly so. What I want to show you is more hidden, more idiosyncratic, but every bit as worthwhile.
Let's start on the North Side. The city is big; about 2.7 million people live here. From downtown, Chicago sprawls north, south and west, so unless you want to spend all day shuttling around on buses and trains, group your activities by location.
Head to Hot Doug's for lunch; plenty of others will be making the pilgrimage with you. The lunch line is always out the door, even in the middle of winter when temperatures can hit 0C. Hot Doug's sells a rotating menu of gourmet sausages, such as the Mandarin Orange and Teriyaki Chicken Sausage.
The cooks' T-shirts proclaim: "There are no two finer words in the English language than 'encased meats', my friend."
Chicago resident Sid Duffour used to come three or four times a week when he worked nearby. He lobbied continuously for the staff to name a sausage after him. Eventually, they created the El Cid - the menu says it's Spanish for "The Sid"; a spicy beef sausage wrapped in bacon.
"That's my legacy," Duffour joked.
"Who needs to have kids? I've got a sausage named after me."
From Hot Doug's head southeast, roughly parallel to the Chicago River, to one of the city's greatest dive bars, of which there are many.
The Old Town Ale House is a bit clean for a dive, but it's hard to see that as a flaw. There's a jukebox, pinball machine, friendly bartenders and almost always someone interesting to talk to. But the oil paintings that cover the walls make the ale house unique.
There's a portrait gallery of the bar's regulars painted by Bruce Elliott, husband of the bar's owner, and a second gallery of Chicago notables such as movie critic Roger Ebert and author Nelson Algren. A third collection of nudes hangs above the bar, including one that earned Elliott more than 100 death threats: Sarah Palin, naked.
The painting depicts the former vice-presidential candidate with a gun, glasses and nothing else. Elliott has done more than 80 talk radio interviews about the piece, and the bar now sells Palin T-shirts and ties.
"This was a weird merging of a semi-porno with politics," Elliott said.
"I had no idea anything was going to come of it. It's amazing what the internet does."
Should the ale house's offerings of booze and nudity leave you with a spiritual hangover, the place to restore your soul is downtown, a little west of the business district.
Irish immigrants built Old St Pat's in the mid-19th century, and it became the city's oldest public building when the older ones burned in the Great Chicago Fire of 1871. The fire missed the church by two blocks.
The interior is astonishingly lovely. Fifteen stained-glass windows twist with the interlocking curlicues of Celtic decoration, their pastel intricacy reminiscent of a monk's embellishments in a medieval manuscript.
The Celtic cross is everywhere except the centre of the altar, where a statue of St Patrick stands instead, a three-leaf clover clutched in his fingers.
More beautiful glass can be found just over a mile east at the Chicago Cultural Centre, which is home to the world's largest Tiffany glass dome, recently restored. The scalloped scales of glass glow gently in the ornate hall, which is frequently rented out for wedding receptions.
The hall's large windows look across Michigan Ave to the Pritzker Pavilion in Millennium Park, just one of the many things in Chicago named Pritzker. Others include a medical school, military library and legal research centre - when you own the Hyatt hotel chain, you have to do something with the money. Millennium Park is named less appropriately, given that the project was finished four years after the millennium and $325 million over budget. Still, charming features like the park's giant, silvery jelly-bean sculpture make it a hit with tourists.
At last we come to the South Side and Hyde Park, 30 minutes south of downtown by public transport, home of the University of Chicago, and now a more famous resident.
Before they moved to the White House, the Obama family lived near the corner of Hyde Park Boulevard and Greenwood Ave, among the mansions of the historic Kenwood district, a former suburb that was annexed by the city in 1889. These were the homes of the men who ran the city's meat-packing plants and lumber yards.
The mansions, mostly brick and stone with the odd Tudoresque throwback or Frank Lloyd Wright masterpiece, sit on double and triple city plots. Walking in the area inspires both disdain for the rich and seething covetousness.
Of course, you can't see the main attraction these days. When the soon-to-be President is home, concrete barriers and metal fences divert traffic for a block in every direction, and police guard the perimeter.
Political activist Chuck Spohr stood near that perimeter on a Friday in early January, having travelled 45 minutes from the suburbs to make a personal gesture of goodwill for the new year.
In one hand he held an American flag, in another a sign that said, "Happy New Era".
Yes, these are good days in Chicago.
Getting there: Air New Zealand flies to Los Angeles and San Francisco from $3149 (plus costs of $149).
Getting around: The Chicago Transit Authority provides the cheapest, easiest way to
navigate Chicago. Visitor passes to ride the city's trains and buses cost between $10 and $39.
Accommodation: When money is no object, stay at The Drake. Rooms range from as low as $236 to almost $4000 for the presidential suite.
House 5863 is located in Andersonville, a North Side neighbourhood with lots of boutiques and dining. Rooms range from $168 to $303.
Days Inn Chicago provides easy access to the heart of the city. Rooms range from $152 to $254.
Attractions: Old St. Pat's
Old Town Ale House
Chicago Cultural Centre - contact culture@cityofchicago.org.
