The lakefront city that gave the world the skyscraper, with river architecture cruises, Millennium Park and deep-dish pizza
Chicago's downtown, the Loop, is framed by the Chicago River and the lake, and its skyline is best appreciated from the water: architecture cruises leave from the 1.25-mile Riverwalk, which runs along the south bank of the river from Lake Michigan to Lake Street past cafés, wine bars and public art. A short walk away, Millennium Park covers 24.5 acres of Grant Park with Cloud Gate, known as The Bean, the Crown Fountain, the Lurie Garden and the Jay Pritzker Pavilion, which hosts free concerts and films in summer. The Art Institute of Chicago stands on the park's southern edge.
The city turns its face to the lake. There are 24 public beaches along 26 miles of waterfront, the Lakefront Trail runs along the shore, and landfill extends into the water for Navy Pier, Northerly Island and the Museum Campus, where the Field Museum, Shedd Aquarium and Adler Planetarium stand side by side. Away from the centre, Chicago is a city of 77 neighbourhoods, from Greektown and Little Italy to Pilsen, Logan Square and Bronzeville, each with its own food and character.
In the mid-eighteenth century the area was home to the Potawatomi, who had succeeded the Miami, Sauk and Meskwaki peoples, and the name comes from a Miami-Illinois word for wild onion or wild garlic. The first known permanent settler was Jean Baptiste Point du Sable, a trader of African descent who established the settlement in the 1780s. Chicago was incorporated as a town in 1833 and as a city in 1837, near a portage linking the Great Lakes and the Mississippi watershed, and it grew rapidly in the mid-nineteenth century.
The Great Chicago Fire of 1871 destroyed several square miles and left more than 100,000 people homeless, and in the rebuilding the city produced the world's first skyscraper, the steel-framed Home Insurance Building of 1885. In 1893 the World's Columbian Exposition drew 27.5 million visitors, and in 1900 engineers reversed the flow of the Chicago River to carry sewage away from Lake Michigan. During the Great Migration the African American population rose sharply, feeding the Chicago Black Renaissance in art, literature and music, and blues, soul, jazz and gospel all became part of the city's musical heritage; Chicago is also the birthplace of house music, and in the 1980s and 1990s it was the global centre of the genre.
Chicago's food reflects its immigrant and working-class roots. The Chicago-style hot dog comes on a poppy-seed bun with mustard, onions, relish, a pickle spear, tomato, sport peppers and celery salt, but never ketchup; deep-dish pizza has been served at Pizzeria Uno since 1943; and the Italian beef sandwich grew out of the city's Italian community in the early 1900s. Puerto Rican Chicagoans gave the city the jibarito, a sandwich made with fried plantains, and Pilsen and Little Village are centres of Mexican American culture. Locals use the 'L' trains and buses, head for the lakefront beaches and patios as soon as summer arrives, and fill free festivals and concerts in the parks.
Most first-time visitors combine an architecture boat tour with a day around Millennium Park and the Art Institute, a stroll along the Riverwalk and the Magnificent Mile, and a museum day on the Museum Campus. Navy Pier has the nearly 200-foot Centennial Wheel, boat rides on the lake and summer fireworks on Wednesdays and Saturdays, while the Lakefront Trail is popular for walking and cycling, with Divvy bike-share stations across the city. Observation decks give views over the skyline, the Chicago Architecture Center runs more than 85 docent-led tours, and in October Open House Chicago opens more than 200 places in over 30 neighbourhoods to visitors for free. Evenings bring blues and jazz clubs, comedy and improv, theatre and, in season, a Cubs baseball game.
Late spring to early autumn is the most popular time: summer averages 26–33°C with festivals, rooftop terraces and boat tours, which generally run from May to October, while October is usually the driest month and brings autumn colour. Winters are cold, with average highs around −1 to 3°C and about 95 centimetres of snow a year, but bring holiday markets, ice skating and light displays.
Checked against the sources on 29 October 2026. Opening times and fees can change — confirm before you go.
General guidance from our specialists, not official information.
The Chicago area, including nearby Oak Park, has the world's highest concentration of Frank Lloyd Wright buildings, and his Prairie-style Robie House is part of a UNESCO World Heritage Site. Jackson Park, site of the 1893 World's Columbian Exposition, and the Museum of Science and Industry lie on the South Side, and Maggie Daley Park, with rock climbing in summer and an ice-skating ribbon in winter, lies across the bridge from Millennium Park. The Ravinia Festival, summer home of the Chicago Symphony Orchestra, is about 40 kilometres north of the city
New Orleans was founded by the French in 1718 on a bend of the Mississippi, and the French Quarter, or Vieux Carré, is the original town: about 85 blocks of Spanish-era townhouses, Creole cottages and iron-lace balconies around Jackson Square. It is the city's most visited neighbourhood and a National Historic Landmark, known for live jazz, Creole restaurants and Bourbon Street's nightlife.
ExploreThe largest city in the United States, spread across five boroughs on the islands and shores of New York Harbor. Manhattan holds the famous skyline, Broadway and Central Park, while Brooklyn, Queens, the Bronx and Staten Island add their own neighbourhoods, beaches and food.
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United States · 9 nights4★ HotelUnited States · 8 nights3★ LodgeThis guide was researched from the sources below and reviewed by our team on 29 October 2026. Facts under “Verified information” link to the page they were checked on; travel tips are general guidance. Photos are credited on each image. The ambient recording’s author and licence are shown in the sound player.
