The Windy City has iconic pizza, ties to blockbuster films and an infamous history of crime and mob funerals – and British Airways offers direct flights
With its blockbuster movie skyline, fabulous food options and notorious crime history, Chicago has plenty to enthrall curious city-breakers. And there’s every type of tour led by clued-up locals to whisk time-pressed travellers straight to the best bits.
Fancy sampling the best deep-dish Chicago pizza? Want to see the church where mob funerals took place? How about gazing at one of the world’s most diverse and shapeshifting skylines while cruising the Chicago River?
Be it by bike, bus, boat or on foot, there are routes carefully crafted by experts and insiders to let the Windy City blow visitors away with the stories of the people who put it on the map.
Chicago is one giant eating adventure with endless famous foods to tick off. With limited time to seek out the prize picks, I took the Tacos and Tequila street-food tour of Pilsen, one of Chicago’s most colourful and culturally rich neighbourhoods.
The three-hour tour, run by Chicago Food Tours Company and led by a local guide, spreads out across 1.5 miles taking in the very best Mexican drinks and dishes.
For £60 you’ll get to make your own tamales – spicy fillings wrapped in corn dough – sample steak tacos, Mexican pork and the most irresistible churros dipped in icing sugar and chocolate, all while admiring the many murals inspired by Mexican culture in the neighbourhood. You’ll also get the all-important lowdown on the best spots to sip margarita cocktails. My kind of town…
I also couldn’t resist delving into its dark underworld with Chicago Crime Tours. The two-hour, £30, bus tour takes you to some of the most Âinfamous crime scenes, landmarks and mobster hangouts, including the site of the Valentine’s Day Massacre in 1929.
Plus you’ll get to hear the true crime stories of Al Capone, The Untouchables, Frank ‘The Enforcer’ Nitti, and the Prohibition era along the way.
If you fancy seeing the sights on two wheels, as well as loading up on food and drink, book on to the Bikes, Bites and Brews tour with Bobby’s Bike Hire.
Working up an appetite is not a problem on this four-and-a-half-hour tour which stretches through the popular neighbourhoods of Streeterville, the Gold Coast, Lake View, Wrigleyville and Lincoln Park. Between riding through the very bike-friendly streets, you’ll stop off for Chicago’s signature deep-dish pizza at Lou Malnati’s.
Lou got his start in the 1940s working in Chicago’s first deep-dish pizzeria. He then took his pizza expertise to Lincolnwood, a northern suburb of Chicago, where he and his wife Jean opened the first Lou Malnati’s Pizzeria in 1971.
Hot dogs Chicago-style at Wrigleyville Dogs are served with seven toppings of yellow mustard, chopped white onions, sweet pickle relish, usually neon green, tomato slices, dill pickle spear, pickled sport peppers and celery salt and come with – shock-horror – no ketchup!
The tour also took in some of the finest cupcakes in the area at Molly’s – try the creme brulee or blueberry cheesecake ones. It then finished with samples of the very refreshing and Chicago-brewed Goose Island beer. After 13 miles on two wheels, I felt like I’d earned every mouthful.
Cruising the Chicago River has to be the most chilled way to take in the city. Chicago’s First Lady Architecture Cruise is a 90-minute boat tour with commentary from Âknowledgeable guides. You’ll hear compelling accounts of Chicago’s architectural styles from Art Deco masterpieces and hulking Brutalist buildings to sleek glass towers, and of the legendary figures who designed them.
Sailing all three branches of the Chicago River, you’ll get to see dozens of the buildings including the neo-gothic Tribune Tower and the 65-storey cylindrical towers of Brutalist Marina City. You also get to learn about the Chicago fire of 1871 and how the city rose, quite literally, from the ashes. Sitting on the shores of Lake Michigan, America’s third biggest city looks spectacular from every angle.
But you can have your own Ferris Bueller moment enjoying the view from The Willis Tower observation deck, Skydeck. Sitting on the 103rd floor, and 1,353ft above ground level, for £23 you are whisked to the top to take in the vista which spans 50 miles across four states – native Illinois, Indiana, Wisconsin and Michigan, on a clear day. Don’t despair if it’s cloudy. As the locals say: if you don’t like the weather in Chicago, wait an hour.
For some extra guidance, download the CityPass app – it lists all the top attractions and you can buy tickets and keep them all in one place too.
Meanwhile, spectator sports in Chicago, including American football, basketball, baseball and ice hockey, provide a thrilling way to see the city and mingle with their fan base.
If you’re just flying in for a few days, you’ll want a hotel close to the action. I stayed at the L7 Lotte Hotel, a brand new Korean-inspired hotel overlooking the Chicago River in downtown Loop, so very convenient for the Magnificent Mile district, Millennium Park, Art Institute of Chicago and Navy Pier. In the bedrooms, sage walls set off contemporary artworks, funky retro headboards and lamps.
Some rooms come with built-in window seats to admire the views – all have all-natural Apotheke toiletries, Nespresso machines and access to the 24-hour fitness centre. The hotel is also home to Perilla, a Korean steak restaurant, renowned for its theatrical table-side grills performed by chefs, which make for a truly memorable meal.
Chicago has a long history of performing close-up magic at restaurant tables and behind bars, with a few jokes and tall tales thrown in while the drinks flow.
At the Chicago Magic Lounge, you can experience this easy-going style of trickery, becoming part of the fun yourself entering through a secret laundry side-door to the part-speakeasy, part-magic theatre. Decorated in Art Deco style, with velvet curtains and gold trims, the bar serves up everything from classic highballs to cocktails like the Magic Bean Martini and How Houdini Died, while magicians perform miracles using coins, cards and anything the audience might have on them.
Fast, funny, and utterly absorbing, it’s an evening that will leave you spellbound and wondering. Chicago may be considered America’s second city, but the appeal of the place that gave the world the skyscraper continues to soar.
