Chicago

Chicago invented the modern skyscraper and never let you forget it

The 1871 fire that destroyed most of Chicago is the reason the city looks like it does. The rebuilding created a laboratory for structural experimentation that nowhere else had the vacancy or the ambition to attempt, and the architects who arrived in the 1880s – Louis Sullivan, Daniel Burnham, John Root, later Mies van der Rohe – effectively wrote the grammar of modern urban architecture in the process. Standing at the corner of Wacker Drive and Michigan Avenue and looking at what surrounds you is the closest thing the United States has to reading the entire history of architectural modernism as a single text. This is not a selling point that appears prominently in Chicago tourism marketing, which prefers deep-dish pizza and “The Bean,” but the architecture is the actual reason the city is worth a serious visit.

The Bean is, however, genuinely good. Cloud Gate in Millennium Park – officially titled Cloud Gate, called “The Bean” by everyone – is a 110-tonne stainless steel sculpture by Anish Kapoor that has been in the park since 2004. The mirror surface reflects a distorted panorama of the Chicago skyline and the people standing around it. It is more interesting than it sounds in description and, unusually for public art, it has not worn thin. The surrounding 24.5-acre Millennium Park is well-managed, free, and features the Frank Gehry-designed Jay Pritzker Pavilion – a legitimate venue, not an ornament – which hosts free concerts through summer.

The Architecture Tour Is Not Optional

The Chicago Architecture River Cruise is the single best thing to do in the city. Expert guides narrate 50-plus buildings visible from the Chicago River over 90 minutes, and the density of genuinely significant architecture on view is unlike anything available in any other American city. Tickets run around $50 and the boats run frequently. The Chicago Architecture Center on Michigan Avenue offers context before or after, and the building it occupies is itself worth the stop.

Willis Tower (the Sears Tower, which most Chicagoans still call by its original name) remains one of the world’s tallest buildings – 442 metres, completed 1973. The Skydeck on the 103rd floor and the glass-floored “Ledge” platform extending out from the building are the standard tourist experience. The views on a clear day extend to four states. The line can be long; book online.

Eating in Chicago

Deep-dish pizza is a legitimate dish and the debate about whether it represents “real” pizza misses the point. It is its own category – a buttery-crusted, cheese-heavy, sauce-on-top construction that was invented at Pizzeria Uno in 1943 and has been argued about ever since. Pequod’s Pizza is the most interesting current version, producing a caramelized crust from cheese melted against the edge of the pan during baking that creates a distinctly different texture from the standard deep-dish. Lou Malnati’s is the most reliable across multiple locations. Bartoli’s Pizzeria has been named best in the city by several publications including the Chicago Tribune; worth the queue.

Alinea, the three-Michelin-star restaurant from chef Grant Achatz, operates in the Lincoln Park neighbourhood. It remains one of the most technically ambitious restaurants in the country. Reservations open on a set schedule and sell out; check the website well in advance.

Portillo’s serves the Italian beef sandwich – thin-sliced beef in gravy, packed into a roll, optional sweet peppers – which is the more important Chicago food heritage contribution than deep-dish and significantly underrated by visitors who came specifically for the pizza.

Neighbourhoods

Wicker Park and Bucktown on the northwest side are where the independent boutiques, galleries, and interesting restaurants actually live. Pilsen, a predominantly Mexican-American neighbourhood on the southwest side, has genuine street murals and a food scene that hasn’t been fully absorbed into the tourism economy yet. The Museum of Mexican Art in Pilsen is one of the best free museums in the city.

The Art Institute of Chicago on Michigan Avenue is the second-largest art museum in the US and has one of the finest Impressionist collections outside Paris. The Grant Wood American Gothic is here. The medieval armor collection is here. It requires a full day to do properly.

Practical Notes

The “L” – the elevated train network – is practical and inexpensive. Weather is genuinely unpredictable; the city’s nickname is accurate. A waterproof layer is not optional. Summer along the 18.5-mile Lakefront Trail is one of the better free activities in any American city.

The Langham Chicago is the luxury reference. Hotel Lincoln in Lincoln Park is the stylish mid-range option with a lively rooftop bar. Both are good. Both will be cheaper if you book a month out rather than a week.