Wind your way around the Windy City with David Whitley’s guide.
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Canvassing for opinions about Chicago tends to generate two responses – those who love it and those who haven’t been.
Los Angeles may have the movies, Boston the history, Washington DC the museums and New York the shopping, but Chicago’s combination of heart, attitude and striking looks tends to win out.
People come for the architecture, and quickly find themselves in love with the big, mid-Western personality.
Sell: Easy rider
The US has no shortage of city-break options, but Chicago’s strength is that it doesn’t feel like hard work. The claustrophobic intensity that can make Manhattan feel a grind after a few days isn’t there – the pavements are wider and it feels as if there’s space between the skyscrapers. The city brims with energy, but it doesn’t burn you out.
Chicago is especially strong as part of an open-jaw ticket, as two of the US’s best-known road trips start there. Route 66 snakes its way west towards Los Angeles, while the Great River Road follows along the Mississippi River through the musical heartlands of Memphis and the Delta.
And it’s music that’s one of Chicago’s undisputable selling points. The city is the home of house music, but its most famous export is the electric blues. When African-Americans made their way north up the Mississippi looking for jobs, they brought their music with them, and it took on an urban edge. Legendary blues clubs – most notably Buddy Guy’s Legends – are still going strong. buddyguy.com
Chicago’s cultural power doesn’t stop at music either. There’s a thriving theatre scene, although it’s comedy where Chicago tends to excel. The Second City club has been the training ground for the likes of Jim Belushi, Bill Murray, Tina Fey and Stephen Colbert. It runs improvisational comedy classes for those who want to try their hand, plus sketch show revues in the evening. secondcity.com
Not that Chicago is short of things to do after dark, and there are plenty of options for those who veer more towards action than words. The Chicago Bears in American football, Blackhawks in ice hockey and Bulls in basketball all have a strong pedigree, but during the summer, baseball is king. The White Sox are the idols of the South Side, but the Cubs have the mythos, partly due to playing at the atmospherically old-fashioned Wrigley Field.
See: Art and architecture
The obvious starting point for any Chicago adventure is Millennium Park, which has impeccable views of the skyline and some of the world’s greatest public art. The Bean, which is officially Anish Kapoor’s Cloud Gate, is an ever-curving, super-reflective mirror that makes people and places look different with every step. Jaume Plensa’s Crown Fountain, meanwhile, features videoed faces on giant walls made of glass bricks. And, every now and then, the faces pucker up and shoot water jets from their mouths.
Millennium Park leads to the more formal Grant Park, which stretches along the shore of Lake Michigan.
At the other end is the Field Museum – arguably the best choice if you’re limiting yourself to just one museum in the city. It covers topics ranging from ancient Egypt to Native American totem poles, but the highlights have a natural history focus. You won’t be able to miss Sue, the largest T-Rex ever discovered. fieldmuseum.org
The massive Shedd Aquarium is practically next door, and is also covered by the commissionable CityPass, which costs $98 for nine days and gives free VIP or fast-pass entry to five of Chicago’s top attractions. citypass.com
Also included within the pass is the Skydeck, the observation platform on the 103rd floor of the Willis Tower. Originally known as the Sears Tower, it was once the world’s tallest building. The Skydeck allows visitors to take in the Chicago skyline from 412 metres up – you look down on skyscrapers, and it’s possible to see four states on a clear day. The highlights are the window booths with see-through floors, which those who fancy their chances of conquering vertigo can step out on to for a rather daredevilish photo opportunity. theskydeck.com
From up there, though, you can’t quite make out the detail, which is often what makes Chicago’s celebrated architecture so special. The Chicago Architecture Foundation runs walking tours of the city, taking in the most impressive buildings. Many are obvious, but the tours go into the back stories and the decoration that can otherwise be missed. The two-hour historic skyscrapers tour ($20) is perhaps the most interesting, as it looks at the oldest (and most lavishly adorned) high rises, rather than the tallest. architecture.org
The absolute must-do, however, is the boat tour that passes along the Chicago River, taking in several of the big-hitters including the neo-gothic Tribune Building and the corn cob-esque Marina Towers ($44). The commentary is highly knowledgeable, and the views as the boat turns around the river bend are astonishing.
Stay: Hotspots
The hot new address is Londonhouse; its prime riverside position and heritage building are key to the appeal, but there’s far more to it than luck of the draw. The hi-tech lift system – enter the floor you want to go to before getting in, so the lifts can be allocated in the most time-effective manner – is a good example. The rooms are modern, with massive TVs, enviably soft sheets and marble-topped bedside tables. Shimmering silver curtains open to unveil outrageous views over the river. And the cherry on top? The rooftop bar with cocktail barmen who mean business. Doubles start at $139 in winter. londonhousechicago.com
Another joint with a remarkable rooftop bar is the Chicago Athletic Association hotel. As the name suggests, it used to be a private sporting club frequented by the wealthy, and nods to the previous incarnation can be found throughout. Leather benches at the end of beds are styled like gym vaulting horses, robes are boxer-style and table legs are wrapped in the same tape as tennis racquets.
It’s a lovely place to explore – with a library area that may as well be a cathedral side chapel, and a games room that includes a bocce court, as well as foosball and pool tables – although the dim lighting may not be to everyone’s taste. Doubles start at $169. chicagoathletichotel.com
Other relatively recent openings include the first Virgin Hotel, which combines sass and thoughtful design. Rooms are spacious, with brightly lit mirrors and rugs adorned with images of London buses and Tube signs. They also feature kettles with Yorkshire tea, while the beds have seat-style backs, so you can sit comfortably on the bed without having to sprawl. Minibar items are charged at street prices and there are free drinks for guests in the Commons Club bar between 6pm and 7pm. Doubles (rooms, not drinks) cost from $131. virginhotels.com
At the more modest end of the scale (prices ramp up in summer), the Essex Inn at the southern end of the city centre is a little tired in places, but offers good value for money. It once had a pool, but that has been replaced by a rooftop garden with sunloungers. Another recent addition is the sauna. Prices start at $107. essexinn.com
