Chicago: The Art of Seduction

The Windy City can't help but seduce you, whether glaring into Millennium Park's gleaming Cloud Gate, dabbling in its molecular gastronomy scene or taking in a legendary blues bar. Just don't forget to look up

By David Whitley
Published 4 Apr 2013, 10:11 BST, Updated 30 Jun 2021, 13:05 BST

As the kayak turns along the river bend, a familiar feeling hits. It's the same sense of exhilarated giddiness that slammed home as I stood awestruck in Millennium Park, the same one I felt cycling down the Lakefront Trail, and the same one I felt staring out over the rooftops from summit of the Hancock Tower.

Chicago's skyline is electrifying. It has an ability to lighten the grimmest of days, and a propensity to turn the biggest cynic into a gibbering, excitable child. But despite all the efforts to clean it up, the Chicago River is not one you want to tumble out of a kayak into. The river does still symbolise the Chicagoan can-do spirit, however. Worried it would contaminate Lake Michigan's supplies  of drinking water, engineers reversed the river's flow and sent the gunk the other way via canal. It worked, and now Chicago dyes the water green every St Patrick's Day for good measure.

The city as it stands today was born from the Great Fire of 1871. It provided a clean slate at the most opportune time. The US railroad system was expanding rapidly and Chicago successfully lobbied to become its hub. With the railroads, the river and Lake Michigan providing boundaries, central Chicago — known as The Loop — had limited space to grow in. And, with the advent of steel frame technology, the only way was up.

The birthplace of the skyscraper is a city of instant, visceral attraction. It's partly due to the bravura design features of the individual components — the corn cob towers of Marina City, the neo-Gothic fantasy of the Tribune building, the shiny, vertiginous gleam of the Trump Tower. But the disparate elements create a staggering whole.

Importantly, it's an allure that doesn't fade as you study the cityscape more closely. The architecture opens the eyes, but the wealth of detail and character opens the heart.

Walking down State Street, I do a double-take at one of the flower beds. Inside are numerous green and white glass pipes, like giant cotton buds, playing jaunty jazz music to confused passers-by. They're one of the many public art projects that can be found across Chicago's neighbourhoods: the Lakefront Trail is lined with odd sculptures, Pilsen is flush with murals, Oz Park in the Lincoln Park district features statues of various characters from The Wizard of Oz.


The most audacious of these public art initiatives is Millennium Park. It may have been delivered late and wildly over budget, but it didn't take long to become a firm favourite with the locals.

Frank Gehry's snaking silver bridge and bulging, mesh-covered Pritzker Pavilion add to a world class ensemble of modern design. The two installations that have been taken closest to Chicagoan hearts, however, are Jaume Plensa's Crown Fountain and Anish Kapoor's Cloud Gate. The former has 15m-tall glass brick towers displaying faces that spit water out at bystanders, while Cloud Gate is an almost impossibly smooth silver 'bean', reflecting the city's skyline at bizarre angles.

Millennium Park follows in the Chicago tradition of not doing things by half. A few blocks to the south via an enjoyable stroll through Grant Park, the Museum Campus is another prominent example. The Adler Planetarium, Shedd Aquarium and Soldier Field — home of the Chicago Bears American football team — can all be found within this scenic complex where you could happily spend the best part of a week.

The king of the campus is the Field Museum, arguably the greatest natural history museum in the world. The headliner here is Sue, the largest and most complete T-Rex skeleton ever discovered, but the mind-boggling depth of the collection makes tackling everything in one visit virtually impossible. Unlike many other natural history museums, it doesn't consist solely of cabinets full of stuffed animals — the scores of separate exhibitions take you on a journey around the globe, making dips into anthropology, evolution and some shamelessly enjoyable 3D movies.

The neo-classical building owes more to Rome than Chicago, though, and a guided tour is the best way to get to grips with the substantial local contribution to the world of architecture. Kayaking trips with Kayak Chicago and numerous boat tours offer a water-borne perspective, but the Chicago Architecture Foundation's walking tours cram in more detail, and are themed to focus on buildings from specific periods.

Up close, the earlier skyscrapers are more intriguing than their flashier, taller counterparts from the late 20th century. The Marquette building, with its intricately decorated terracotta exterior, is a perfect example. It also offers an important lesson. So many visitors stare at Chicago's buildings without thinking to venture inside them. The lobby of the Marquette is dominated by glass, gold and mother of pearl mosaics telling the story of the Chicago area's discovery by Jacques Marquette in 1674.


Other classic buildings have since been converted into hotels. The Reliance Building — generally regarded as one of the first modern skyscrapers, if not the first — plays host to the Burnham. It has been considerably sassed up by the Kimpton chain, offering great little bonuses such as free bike hire and complimentary wine between 5pm and 6pm. But the communal areas still retain heritage features, while displays explain the bizarre and fascinating two stage construction of a building that would become a prototype for tens of thousands worldwide.

Elsewhere, the InterContinental's South Tower was originally built as the Medinah Athletic Club in 1929 — a hang-out for Chicago's rich and famous. The Spanish-themed 14th floor pool is one of the most lavish you'll ever see.

The pool at the Essex Inn, meanwhile, just south of The Loop, isn't quite as grandiose — but at least there is one. Added to smart rooms, a decent location and rates that are low by Chicago's standards, it offers the best value in town.

Other relative bargains can be found by going beyond the Loop, to the Near North and Gold Coast districts, where most hotels are concentrated. Slightly further north, with a prime location on the edge of Lincoln Park, the Hotel Lincoln is a good example — 60% of the rooms have lake views, while the lobby, restaurant and rooftop bar have a tangible buzz. It's a part of the community rather than a hotel that just happens to be plonked in the area. Some quirky furniture design and an abundance of old photographs of the city bring a mildly theatrical, vintage Chicago feel to the property.

At the top end of the market, the Waldorf Astoria on the Gold Coast remains the benchmark — it's almost an art gallery in its own right, the service is excellent without being obsequious and the suites are both tasteful and sprawling.


Somewhat unsurprisingly, the swanky Gold Coast and Near North hotels are all within spitting distance of Chicago's grandest shopping strip.

Stretching along North Michigan Avenue from the river to the high-end boutiques of Oak Street, the Magnificent Mile is where credit cards can take quite a bashing. Disney, Apple, Cartier, Timberland, Zara and Levi's are just a few the big names that have mammoth stores along the route.

Suitcase-stuffers on shopping missions generally don't need to venture much further afield, but those on the hunt for something more distinctive are better off strolling along Armitage Avenue in the Lincoln Park area. It's posh baby buggy territory, but with plenty of small independent stores. The Comfort Me Boutique works the boho chic vibe and All She Wrote does cutesy stationery and giftware, while Vosges Haut Chocolat offers high-end chocolates flavoured with everything from cherry blossom to rare Spanish saffron.

Foragers are best suited to North  Milwaukee Avenue in the Wicker Park neighbourhood, however. Between North Avenue and Division Street are an extraordinary number of clothing and record exchange stores. The quality control is high here, making this a fertile hunting ground for vintage outfits and rare vinyl.


Wicker Park and conjoined twin Bucktown are also home to some of Chicago's most interesting and affordable places to eat. Chicago Food Planet operates walking — and munching — tours through the area, kicking off with a locally-beloved Chicago-style hotdog at George's. Guide Kent explains the rules as the food is brought out: "They have to be made from Vienna beef — the Vienna factory is just a few blocks away from here. And you must never put ketchup on them," he adds. Mustard is practically obligatory, however, as is the unusual vegetable garden of adornments.

It quickly becomes clear why Chicagoans won't touch a hotdog made anywhere else. It's meaty, well-seasoned and slightly spicy — rare qualities in a snack usually associated with low-grade fast food.

The tour also covers Sultan's Market, home of stellar falafel sandwiches, and Hot Chocolate, best known for the desserts hand-crafted by Mindy Segal — she was recently named the best pastry chef in the city.

Things are a little more high-tech at iCream which uses a liquid nitrogen system to custom-make ice creams and frozen yoghurts with pretty much any flavours or toppings you could wish for. "I'm told there are over a million possible combinations," says Kent. The appliance of science is what has made Chicago a culinary hotspot in recent years. In the vanguard has been molecular gastronomy pioneer Grant Achatz, whose Alinea is regularly called the best restaurant in the country. Alas, you've no chance of eating here unless you reserve months in advance, so you're better off heading to West Randolph Street in the Near West Side instead.

This strip is rapidly gentrifying, but traditional wholesalers still remain, among restaurants that are the hippest in town until another one opens up a couple of weeks later. The oddly rustic-meets-industrial Au Cheval takes food classics and works fine dining magic on them, while Blackbird veers towards gamey and rich, with killer cocktails to wash things down with.


Towards the western end of West Randolph Street, the City Winery offers a huge range by the glass as a result of storing the wines in the barrels rather than buying in bottles. The huge, sociable patio has seen it become a humming, somewhat flirty hangout, particularly for the rowdy after-work crowd that ends up there for a few hours longer than intended.

Chicago is more a beer than a wine city, however. If you want old soaks propping up the bar, talking sport and other assorted nonsense, the Clark Street Ale House is a tremendous spot in which to put the world to rights over a glee-inducing array of Midwestern microbrews.

If you want good food during your real ale marathon, then Hopleaf in Andersonville should be your next port of call. It's deceptively large — the small bar by the entrance opens out into a multi-room affair spanning the pub/restaurant divide.

There's an emphasis on Belgian-style beers among the intimidatingly large list, but some of the beers are made with input from highly respected Chicago chefs. There's no fear of experimentation.

That's something that applies at The Second City comedy club, too, a long-standing Chicago haunt that has been turning out top comics since 1959. Dan Ackroyd, John and James Belushi, Bill Murray, Steve Carell and Tina Fey are among the alumni, while the current generation doesn't pull any punches on stage. For those who want to test their improv chops, there are drop-in classes for beginners on Sunday evenings.

Chicago has a rich historical seam of comedy, but that's trumped by its musical pedigree. This is where the blues urbanised, and scene stalwart Buddy Guy still runs the Legends blues club on the South Side. It's not cutting edge any more, but that doesn't matter a jot once you're swept along with the guitars and croaking voices.

The same applies at the wonderfully atmospheric Green Mill, an old-school cocktail joint where jazz is listened to with hushed reverence. It still retains its indulgent prohibition-era speakeasy decor, and a walk inside brings back that now-familiar Chicago feeling — dumbfounded awe, with a sizzling current of excitement surging through the body. I believe it's called 'razzle dazzle'…


Getting there
British Airways, United Airlines and Virgin Atlantic fly from Heathrow to Chicago O'Hare, while American Airlines flies from Manchester, Dublin and Heathrow.

Average flight time: 8h

Getting around
From O'Hare, a taxi to central Chicago will cost from $40 (£25) and take up to an hour. The Blue Line train takes the same time and costs only $2.25 (£1.40). The El (elevated train) acts as Chicago's metro, and covers most places of interest. Buses fill the gaps, and the journey planner on the Chicago Transit Authority website helps you plot the best combo. Public transport day passes cost from $5.75 (£3.59).

Taxis aren't horrendously expensive unless there's gridlock. Yellow Cab is a reliable firm. T: 00 1 312 829 4222.

The city is flat, making cycling a good way to get around. Bobby's Bike Hike offers bike rentals from $23 (£14) per half day, as well as a variety of themed cycling tours.

Kayak Chicago runs tours on the water, and offers kayak rentals from $20 (£12) an hour.

When to go
The summer — June to September — sees Chicago at its best, with festivals seemingly springing up on every corner.

Need to know
Visas: UK citizens must travel under the ESTA visa waiver scheme priced at $14 (£8.75) arranged in advance of departure.
Currency: US dollar (USD). £1 = $1.60.
International dial code: 00 1.
Time difference: GMT-6.

How to do it
Travelbag offers five nights at the Essex Inn, staying on a room-only basis, from £699 per person, including flights with KLM from Heathrow. 

Published in the March 2013 issue of National Geographic Traveller (UK)

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