The steel-grey surface of Lake Michigan behaves more like an ocean than a lake, kicking up whitecaps that batter the concrete rim of the Gold Coast. Above, the city rises in a defiant grid of glass and limestone, a monument to the 1871 fire that razed the town and allowed a generation of architects to treat the Illinois prairie as a blank sketchpad. Chicago does not possess the frantic, vertical anxiety of New York or the sprawl of Los Angeles. Instead, it offers a muscular, midwestern elegance—a city of broad shoulders, deep-dish convictions, and a lakefront that remains public property by law.
The Skyline as a Museum
Chicago is the birthplace of the skyscraper, and the best way to comprehend this is from the water. Skip the generic sightseeing barges and book the Chicago Architecture Center River Cruise aboard the First Lady. For 90 minutes, docents explain the transition from the neo-Gothic flourishes of the Tribune Tower to the brutalist "corncobs" of Marina City.
On land, the Loop serves as the city’s historic heart. Walk to the corner of South Dearborn Street to find the Monadnock Building. The north half, built in 1891, is the tallest load-bearing masonry building in the world; its walls are six feet thick at the base to support its own weight. Contrast this with the Willis Tower (formerly the Sears Tower) on Wacker Drive. While the Skydeck is the famous draw, the view from the 95th-floor lounge of the 875 North Michigan Avenue building (formerly the John Hancock Center) is superior, offering a direct sightline down the shoreline of Lake Michigan.
In Millennium Park, look past the heavy crowds at Anish Kapoor’s Cloud Gate (the Bean) to find the Jay Pritzker Pavilion. Designed by Frank Gehry, its brushed stainless steel ribbons create an acoustic canopy that hosts free orchestral rehearsals on summer afternoons.
A Tale of Two Sandwiches
To eat in Chicago is to engage in a lifelong argument about bread and condiments. The city’s identity is forged in two specific vessels: the deep-dish pizza and the Italian Beef.
For pizza, ignore the national chains. Head to Pequod’s Pizza on North Clybourn Avenue. Unlike the doughy troughs found elsewhere, Pequod’s is famous for its "caramelised crust"—a ring of blackened mozzarella that forms a salty, crunchy halo around the pan. Order the sausage and pepperoni; the wait for a table usually exceeds an hour, so put your name in and find a stool at a nearby dive bar.
The Italian Beef is a different beast entirely. At Al’s Beef on West Taylor Street, the ritual is specific. Thinly sliced roast beef is simmered in "gravy" (jus) and tucked into a French roll. You must specify your order: "Dry," "Wet," or "Dipped" (the entire sandwich submerged in the pot). Always top it with giardiniera—a spicy, oily mix of pickled serrano peppers, celery, and olives. Eat it in the "Chicago Lean," elbows on the counter and body angled forward to prevent the gravy from ruining your shoes.
Neighbourhoods Beyond the Loop
The true pulse of the city is found in the 77 distinct community areas. To the northwest, Wicker Park and Logan Square serve as the creative hubs. Walk down Milwaukee Avenue to find Myopic Books, an award-winning second-hand bookstore with floor-to-ceiling stacks that smell of old paper and dust. Afterwards, grab a table at Lula Cafe in Logan Square, a pioneer of the farm-to-table movement that serves a legendary Sunday brunch.
Further north is Andersonville, a historically Swedish enclave. Check out the Hopleaf on Clark Street, a Belgian-style tavern with an encyclopedic beer list and some of the best moules-frites in the Midwest. In the south, Hyde Park offers a more academic, serene atmosphere. It is home to the University of Chicago and the Robie House, Frank Lloyd Wright’s masterpiece of Prairie School architecture. The house, with its long horizontal lines and leaded glass windows, looks as though it is growing directly out of the Illinois soil.
For a taste of old-world Chicago, visit Pilsen. This Mexican-American neighbourhood is defined by the 18th Street corridor, lined with street art and bakeries. Stop at Panaderia Nuevo Leon for conchas and then head to the National Museum of Mexican Art, which houses one of the most significant collections in the country.
Rhythm and Blue Notes
Chicago’s musical history is stitched into the Great Migration, when Black Southerners brought the Delta blues north and electrified it. On the South Side, Buddy Guy’s Legends remains a temple to the genre, with the man himself often appearing on stage in his signature polka-dot shirt.
For a more intimate, grit-under-the-fingernails experience, go to Kingston Mines in Lincoln Park. It features two stages and live sets that run until 4:00 am. The walls are covered in memorabilia, and the ribs are sticky. If jazz is the preference, The Green Mill in Uptown is non-negotiable. Once a regular haunt for Al Capone, it retains its 1920s Art Deco booths and a strict "no talking during the set" policy. It is one of the few places where the ghosts of the Prohibition era feel tangible.
The Lake and the Island
The 18 miles of the Lakefront Trail provide the city’s lungs. In the summer, the lake is the primary social club. North Avenue Beach is the busiest, but for something quieter, head to Promontory Point in Burnham Park. This man-made peninsula offers a limestone stepped sea wall where locals grill, swim, and watch the skyline shimmer in the distance.
Winter in Chicago is a test of character. From January to March, "The Hawk"—the biting wind off the lake—slices through the streets. However, visiting during the shoulder seasons of May or September provides the best balance. In September, the humidity has broke, the Cubs are likely still playing at the ivy-covered Wrigley Field, and the light on the water turns a sharp, brilliant copper.
Getting Around: The L
Chicago is a city best navigated via the ’L’ (elevated train). The Brown Line is the most scenic, looping through the downtown skyscrapers before heading north through residential neighbourhoods. The Blue Line runs 24 hours a day, connecting O’Hare International Airport to the city centre.
Avoid renting a car. The grid system is logical, but parking is a bureaucratic nightmare. Use the Ventra app to load a 3-day or 7-day pass onto your phone. If the weather is fair, the Divvy bike-share system is extensive, though cycling in the Loop requires a high tolerance for aggressive taxis and potholed asphalt.
If You Go
When to visit: Late May for the blooming of the parks, or September for the Jazz Festival and mild temperatures. Avoid February unless you enjoy sub-zero wind chills.
Transport: O’Hare (ORD) is the primary international hub. Take the Blue Line train into the city (approx. 45 minutes). Midway (MDW) handles domestic flights and is served by the Orange Line.
What to pack: Layers. Even in July, the temperature can drop 10 degrees the moment you walk toward the lake. Bring comfortable walking shoes; Chicago is a flat city, and you will rack up miles without noticing.
Local etiquette: Never, under any circumstances, ask for ketchup on a Chicago-style hot dog. A proper dog at Portillo’s or Gene & Jude’s comes with mustard, neon-green relish, chopped onions, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt. Ketchup is considered a personal insult to the vendor.
10 best things to do in Chicago
- Art Institute of Chicago
- Chicago Architecture Center River Cruise
- Millennium Park
- The 606
- Skydeck Chicago at Willis Tower
- Field Museum
- Wrigley Field
- Museum of Science and Industry
- Lincoln Park Conservatory
- The Magnificent Mile