Three cheers for Chicago

Head to the Windy City and become a culture vulture

Why go?

While New York dazzles with its bright lights and brash attitude, Chicago quietly impresses with its architecture, huge cultural scene, and chilled-out vibe. Situated in northern Illinois, at the southwestern tip of Lake Michigan, it boasts fresh seafood and delicious cuisine influenced by the multicultural residents of its 77 neighbourhoods. And despite being the third largest city in America, it never feels too large or intimidating. In fact, the gorgeous aquamarine river that runs through it, and the 37 bridges crossing it, add an air of tranquillity to the city.

Explore

The CAFC River Cruise is a must. With knowledgeable guides, you get a fantastic sense of the city and its origins from the river, and will be bowled over by the famous architecture during the 90-minute tour. Alternatively, a visit to The Ledge at Skydeck Chicago offers breathtaking aerial views of the city from the 103rd floor of Willis Tower. The highest observation deck in America, you can see for 50 miles on a clear day, and the glass viewing platforms provide the perfect backdrop for a selfie. However, if you’re nervous about heights, you can still get a fab shot from the safety of the carpeted area. Also, make time for the interactive experience celebrating Chicago’s history and neighbourhoods. Don’t worry if you’re on a budget because there are plenty of things to do. The river walk is a nice way to take in the sights, while downtown

Millennium Park has lovely gardens to explore – Anish Kapoor’s popular Cloud Gate sculpture for one, and the impressive Jay Pritzker Pavilion, which offers free outdoor music concerts. If you have time, it’s great to jump on the Metro to Andersonville, a neighbourhood on the north side that has Swedish roots and a lovely community spirit. Take in the colourful street art by local artists and rummage through the treasure trove of thrift and independent stores.

After dark

Chicago is famous for its jazz and blues scene. If you’re looking for something fancy, dress up and head to Jazz At Tortoise Supper Club (Tortoisesupperclub.com), where you’ll be treated to mouth-watering food ­and live jazz. If you’re after a more casual vibe, then try Kingston Mines Blues Club (Kingstonmines.com), the oldest and largest blues club in Chicago, which has a great atmosphere, good drinks selection, and fantastic musical guests.

Food and drink

In terms of food, whatever your preference, you really are spoilt for choice. For lunch, we liked celebrity favourite Al’s Beef (Alsbeef.com), which is famous for its succulent Italian beef sandwiches and does a mean veggie burger. Bang Bang Pie & Biscuits (Bangbangpie.com) is a cool café that specialises in Mid-Western cooking and serves a feast of sweet and savoury pies that you’ll struggle to choose between. Plus, it’s probably illegal, or at least should be, to leave Chicago without sampling the legendary deep-dish pizza. We went to Giordano’s (Giordanos.com) and had the Super Veggie, which was delicious and enormous. One of our favourite meals was at Eataly, Vino &… [{href='http://(Eataly.com' target='_blank' rel='noreferrer noopener'}), which is a reasonably priced Italian restaurant, that allows you to buy the wine and high-quality ingredients you consumed to recreate at home. Our Cacio y Pepe pasta was cooked to perfection and the Insalata di Cavolo Nero was a brilliant accompaniment. If you’re looking to splash out, we’d recommend Lyra (lyrarestaurant.com) in buzzy Fulton Market, which has an incredible Greek menu, including the most tender octopus we’ve ever tasted.

Where to stay

We stayed in the Canopy By Hilton Central Chicago Loop hotel, which is in the financial district, opposite the iconic Willis Tower. Newly opened in November 2021, the former Chicago & North Western Railway Company Building draws inspiration from the golden age of train travel and has a lovely art deco feel. The beautifully decorated rooms are incredibly spacious, plus they had a steamer for our suitcase-crumpled clothes, a caffeine-boosting Nespresso machine, and sustainable glass water bottles that can be refilled on every floor whenever you wish. As for breakfast, there are many treats on the menu, including seasonal-flavoured frittatas and homemade breads and pastries. Make sure you try the game-changing smashed avocado on 
five-grain toast, and orange and pistachio sweet roll.

Need to know

Words: Kay Ribeiro