Chicago, Illinois

Chicago’s architecture boat tours are the most efficient thing you can do in any American city. In 90 minutes on the Chicago River, you pass structures by Louis Sullivan, Mies van der Rohe, Frank Gehry, and Jeanne Gang while a knowledgeable guide explains not just who designed what but why Chicago became the city where American architecture was invented. The city burned down in 1871 – the Great Fire destroyed 17,000 buildings – and what replaced it over the next four decades was essentially a live experiment in how to build tall. Every major convention in modern architecture either started here or had its most important arguments here. Knowing that changes what you see when you walk around.

Chicago is the third-largest city in the United States, and it has a justified chip on its shoulder about New York. The food is better in several categories. The lakefront is better. The architecture is arguably better. The people who live here will tell you this; the people who visit and stay longer than a weekend will often quietly agree.

Millennium Park and the Loop

Millennium Park, opened in 2004 on a former rail yard, contains Anish Kapoor’s Cloud Gate – the Bean, as everyone calls it – which the city renovated for 2026 with improved accessibility. The 110-tonne reflective steel surface warps the skyline and the people standing in front of it in ways that never entirely get boring. Crown Fountain nearby projects video faces of Chicago residents onto two 50-foot glass towers; the Jay Pritzker Pavilion, designed by Frank Gehry with stainless steel ribbons for a bandshell and a trellis covering the Great Lawn, hosts free outdoor concerts from May through August as part of the 2026 Summer Music Series.

The Art Institute of Chicago, directly adjacent, holds Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, and what is genuinely one of the strongest Impressionist collections in the world outside Paris. The Modern Wing added in 2009 substantially expanded the contemporary holdings. A day here is not an exaggeration.

Willis Tower (formerly Sears Tower, completed 1973, held the world’s tallest building title for 22 years) has a Skydeck on the 103rd floor and the Ledge, glass-floored balconies extending four feet beyond the facade. Buy tickets in advance to avoid lobby queues.

Wrigley Field

Wrigley Field was built in 1914, making it the second-oldest Major League Baseball stadium still in use. The hand-operated scoreboard, ivy-covered outfield walls, and the informal economy of rooftop bleachers on the surrounding buildings have survived nearly every renovation. The 2026 season introduced new concessions including a chargrilled Vienna dog on a bao bun – a minor but telling sign of how carefully the ballpark manages the line between tradition and the current moment. Tours run from March through September and include the press box, bleachers, and field access on non-game days. Games during warm weather months sell out quickly; plan ahead.

Food

Deep-dish pizza: Chicago deep-dish has a thick buttery crust pressed up the sides of a steel pan, with cheese on the bottom, fillings in the middle, and chunky tomato sauce layered on top. It bakes for 45 minutes and is best understood as a casserole, not a traditional pizza. Lou Malnati’s (since 1971, proprietary sausage blend) and Pequod’s in Lincoln Park (caramelised cheese crust where the cheese meets the pan edge) are the two most defensible choices.

Italian beef: Thinly sliced seasoned roast beef on an Italian roll, ordered wet (fully dipped in cooking juices), dry, or dipped on one side, with spicy giardiniera relish. This is uniquely Chicago. Portillo’s and Al’s Beef are the longstanding spots.

Chicago-style hot dog: All-beef frankfurter on a poppy seed bun with yellow mustard, white onion, neon-green sweet pickle relish, a dill pickle spear, tomato slices, sport peppers, and celery salt. No ketchup. The absence is not accidental. Vienna Beef has supplied the franks since 1893.

Girl & the Goat in the West Loop: Chef Stephanie Izard’s flagship runs shared plates with bold combinations. Reservations weeks ahead.

Neighbourhoods

The 606 Trail runs 2.7 miles through Bucktown, Wicker Park, and Logan Square on a former elevated rail line. The Chicago Riverwalk along the main branch has kayak rentals, outdoor dining, and architecture tour departures. Pilsen on the south side has a strong Mexican American cultural identity, the National Museum of Mexican Art, and murals that are as serious as gallery work. Bronzeville, further south, has direct ties to the Great Migration and the development of Chicago blues, jazz, and gospel.

Getting Around

The CTA ‘L’ train connects both airports (O’Hare on the Blue Line, Midway on the Orange Line) to downtown and covers most major areas. A 24-hour or 3-day pass is cost-effective. Chicago’s weather shifts fast: summer humidity can reach the 90s Fahrenheit, winter lake-effect wind pushes effective temperatures well below freezing. Any visit requires layering regardless of the forecast.

The Museum Campus at the south end of Grant Park clusters three major institutions: the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium. A combination pass reduces cost. Arrive at opening time; crowds build significantly by mid-morning.