Chicago, USA: Travel Guide to the Windy City on Lake Michigan

Chicago, on the shores of Lake Michigan, is the third-largest city in the United States and one of the world's great architectural capitals. After the Great Chicago Fire of 1871 destroyed much of the city, architects rebuilt it with bold new ideas, and in 1885 Chicago gave the world its first skyscraper. Today, the "Windy City" dazzles visitors with its stunning skyline, world-class museums, lakefront beaches, legendary blues and jazz clubs and famous deep-dish pizza.

Top 5 Must-Visit Attractions in Chicago

1. Chicago Architecture River Cruise

The best way to understand Chicago's skyline is from the water. An architecture river cruise along the Chicago River glides past more than 40 landmark buildings, from the Gothic Tribune Tower and the Art Deco Carbide & Carbon Building to the twin "corncob" towers of Marina City and the sleek Trump International Hotel and Tower. Expert guides explain how Chicago became a laboratory for modern architecture, home to pioneers such as Louis Sullivan, Frank Lloyd Wright and Ludwig Mies van der Rohe. The tour run by the Chicago Architecture Center is widely considered one of the best tours in the United States.

Booking tip: architecture river cruises often sell out in summer; book on GetYourGuide in advance, and choose a sunset cruise for spectacular views.

2. Millennium Park and the Art Institute of Chicago

Millennium Park, opened in 2004, is Chicago's outdoor living room. Its star attraction is Cloud Gate, the giant mirrored sculpture by Anish Kapoor, nicknamed "The Bean," which reflects the skyline and visitors. Nearby, the Crown Fountain features video faces of Chicagoans spouting water, and the Jay Pritzker Pavilion, designed by Frank Gehry, hosts free summer concerts. Next door, the Art Institute of Chicago houses one of the world's finest art collections, including Edward Hopper's Nighthawks, Grant Wood's American Gothic, Georges Seurat's A Sunday on La Grande Jatte and an outstanding collection of Impressionist paintings.

Booking tip: skip-the-line tickets for the Art Institute can be booked on GetYourGuide; allow at least half a day.

3. Skydeck at Willis Tower and 360 Chicago

At 442 metres, the Willis Tower (formerly Sears Tower) was the world's tallest building when completed in 1973. Its Skydeck on the 103rd floor offers views across four states on a clear day, and The Ledge, a set of glass boxes extending from the building, lets you stand over the city 412 metres up. On the Magnificent Mile, 360 Chicago, at the top of the John Hancock Center, offers TILT, a platform that tilts visitors out over the city.

Booking tip: visit at sunset; Skydeck tickets can be booked on GetYourGuide.

4. Museum Campus and the Lakefront

On the lakefront, the Museum Campus brings together three major institutions: the Field Museum, home to SUE, one of the largest and most complete T. rex skeletons ever found; the Shedd Aquarium, with beluga whales and coral reefs; and the Adler Planetarium, America's first planetarium, with superb skyline views. The Lakefront Trail, stretching about 29 kilometres along Lake Michigan, is perfect for cycling, with beaches such as North Avenue Beach and Oak Street Beach. Navy Pier offers a Ferris wheel, boat tours and summer fireworks.

Booking tip: a Chicago CityPASS can save money on multiple attractions.

5. Wrigley Field, Blues Clubs and Neighbourhoods

Wrigley Field, home of the Chicago Cubs since 1916 and opened in 1914, is one of the oldest ballparks in Major League Baseball, famous for its ivy-covered walls. Chicago is also the home of electric blues, and clubs such as Kingston Mines and Buddy Guy's Legends offer live music nightly, while the Green Mill, a jazz club once frequented by Al Capone, is a historic gem. Explore neighbourhoods such as Wicker Park, Pilsen and Chinatown for food and street art.

Booking tip: Wrigley Field tours and Chicago food tours can be booked on GetYourGuide.

Practical Travel Tips for Chicago

Before You Go

• Entry: most visitors from visa-waiver countries must apply for an ESTA online before travelling to the United States; check current requirements and fees.

Getting Around

• By air: O'Hare International Airport, one of the world's busiest, and Midway Airport are both connected to the city by the 'L' trains.
• The 'L': Chicago's elevated and subway train system is the easiest way to get around; use a Ventra card or contactless payment.
• Divvy bikes: bike-sharing is popular along the lakefront.
• Money: the currency is the US dollar; tipping 18–20 per cent is customary in restaurants.

Local Culinary Specialties

• Deep-dish pizza: a thick, buttery crust filled with cheese and tomato sauce; try Lou Malnati's or Giordano's.
• Chicago-style hot dog: an all-beef hot dog "dragged through the garden" with mustard, onions, relish, tomato, pickle, peppers and celery salt, but never ketchup.
• Italian beef sandwich: thinly sliced beef soaked in juice.
• Garrett Popcorn: a mix of caramel and cheese popcorn.

Best Time to Visit

• May–October: warm weather, festivals and outdoor activities.
• March: the Chicago River is dyed green for St. Patrick's Day.
• August: the Lollapalooza music festival in Grant Park.
• Winter: very cold and windy, but with holiday markets and ice skating.

Conclusion: Plan Your Trip to Chicago

Chicago combines spectacular architecture, world-class art, lakefront beaches and legendary food and music. Whether you're cruising the river, standing on The Ledge or eating deep-dish pizza, the Windy City will win you over.

Plan ahead: book your tours on GetYourGuide, and get ready to discover Chicago.