Chicago: The City That Burned Down in 1871 and Rebuilt Itself Into the Most Architecturally Significant Skyline in the World

The Great Chicago Fire of 1871 destroyed roughly 17,000 buildings and left 100,000 people homeless. The city rebuilt on the same street grid within two years, this time in brick and stone rather than wood, and used the reconstruction as an opportunity to invite the best architects in the country to experiment on a scale that New York, with its older building stock, could not offer. What followed over the next century – Sullivan, Burnham, Mies van der Rohe, SOM – created the most concentrated collection of significant 20th-century architecture in the world.

This is the reason to come to Chicago, or at least the highest-return reason. The food is exceptional, the lake is enormous and free, and the museums are world-class. But the buildings are the thing.

Architecture

The Chicago Architecture Center River Cruise (about USD 55 per person) covers 50-plus buildings in 90 minutes from the Chicago River. Run multiple times daily from May through November. This is the best single investment you can make on a Chicago visit. Book online.

Millennium Park is free and contains the Cloud Gate sculpture (the Bean) by Anish Kapoor, the Frank Gehry Pritzker Pavilion, and the Crown Fountain – 50 acres of public space in the middle of the city that actually works.

The Chicago Cultural Center on Michigan Avenue at Washington Street was the main public library until 1991. The interior has two rooms with Tiffany glass domes – one mosaic, one stained glass – that are among the most extraordinary interiors in any public building in America. Free entry. Most tourists walk past it, which is a significant error.

Frank Lloyd Wright’s Oak Park buildings are 20 minutes on the L Blue Line: the Unity Temple and his home studio, the highest concentration of Wright buildings anywhere in the world. Worth a half-day if architecture is your primary interest.

The Art Institute

One of the top five art museums in the United States. The permanent collection includes Seurat’s Sunday on La Grande Jatte, Hopper’s Nighthawks, and Grant Wood’s American Gothic. The Thorne Miniature Rooms – 68 rooms at 1:12 scale representing European and American interior design from the medieval period to the 1930s – are fascinating in a way that is hard to explain in advance. Admission around USD 32. Give it three hours minimum.

Eating

Alinea in Lincoln Park holds three Michelin stars. The tasting menu runs USD 300 to 400 per person; courses arrive on the table surface, as edible art installations, in sequences that treat flavour and presentation as inseparable. Book three months ahead. It is either the best meal of your life or genuinely not your thing; very little middle ground.

Girl and the Goat in West Loop: small plates, whole-animal cooking, excellent cocktails. James Beard Award winner. Reservations weeks ahead, USD 40 to 60 per head.

Lou Malnati’s is the reference Chicago deep-dish: a butter crust, layers of mozzarella, chunky tomato sauce on top (reversed from conventional pizza logic). The sausage pizza is the original order and takes 45 minutes to bake. About USD 20 for a personal pizza.

Portillo’s on Clark Street does Chicago-style hot dogs (Vienna Beef frank, yellow mustard, onions, relish, tomato, pickle, celery salt, never ketchup) and Italian beef sandwiches under USD 10. This is genuine Chicago working-class food culture and it is correct.

The Neighbourhoods

Wicker Park and Bucktown northwest of the Loop: the best independent restaurant and bar concentration. Walk Milwaukee Avenue from Division Street north.

Pilsen on the near south side: the Mexican-American neighbourhood with excellent taquerias, building murals everywhere, and the National Museum of Mexican Art (free admission). The tamales and birria on 18th Street are as good as anything in the city.

Getting Around

The L (elevated rail): a single ride is USD 2.50, a 24-hour pass is USD 10. The Blue Line runs 24 hours and connects O’Hare Airport to the Loop for USD 2.50. Walking between the Loop, Millennium Park, and River North is often faster than driving.

June through early September is the pleasant window. Chicago’s winters hit below -20 Celsius with wind chill; January and February are punishing.