A city of skyscrapers, lake views, and deep-dish pizza.
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Overview
Chicago, located on the southwestern shores of Lake Michigan in Illinois, USA, is one of America's largest and most dynamic cities. Renowned for its groundbreaking architecture, world-class museums, vibrant arts scene, and innovative culinary landscape, Chicago offers a captivating blend of urban sophistication and Midwestern charm. From its towering skyscrapers to its lively neighborhoods and extensive green spaces, the "Windy City" is a major cultural and economic powerhouse.
While Chicago is an inland city and not an ocean cruise port, it is a significant and popular pre or post-cruise land extension for passengers on Great Lakes cruises (with embarkation/disembarkation often in Milwaukee, Detroit, or Toronto), or for those undertaking transcontinental rail journeys that connect to ocean or river cruises. Its status as a major international airport hub also makes it a common entry or exit point for travelers. A visit to Chicago offers cruise passengers an extraordinary opportunity to explore a bustling metropolis, admire architectural masterpieces, indulge in diverse cuisine, and experience the energy of a quintessential American city.
Embark on an architecture river cruise along the Chicago River. This is arguably the best way to experience Chicago's world-famous skyline and learn about the city's architectural innovations from expert guides. You'll see iconic buildings like the Willis Tower, Tribune Tower, and Marina City.
Tip: Book your cruise in advance, especially during peak season. Daytime cruises offer the best visibility for architecture details.
Immerse yourself in art at the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Its vast collection spans centuries and cultures, featuring masterpieces from Impressionism (e.g., Seurat's A Sunday on La Grande Jatte), American art, and contemporary works.
Tip: The museum is immense; prioritize sections based on your interests or focus on key highlights if time is limited. Arrive early to avoid crowds.
Stroll through Millennium Park, a vibrant urban park that showcases stunning public art, including the iconic Cloud Gate (informally known as "The Bean"), a giant reflective sculpture. Also, see the Crown Fountain and enjoy free concerts at the Jay Pritzker Pavilion during summer.
Tip: "The Bean" is a popular photo op; try different angles for unique reflections. The park is easily walkable from many downtown hotels.
Gain breathtaking panoramic views of the city skyline, Lake Michigan, and beyond from one of Chicago's famous observation decks. Choose between the Skydeck at Willis Tower (with its glass Ledge) or 360 Chicago at the former John Hancock Center (with its thrilling TILT experience).
Tip: Purchase tickets online in advance to reduce wait times. Visit during non-peak hours (early morning or late evening) for fewer crowds.
Indulge in a culinary icon: Chicago deep-dish pizza. Try a slice (or several!) at one of the city's renowned pizzerias like Lou Malnati's, Giordano's, or Gino's East. Be prepared for a thick crust, generous cheese, and robust tomato sauce.
Tip: Deep-dish takes longer to cook than regular pizza, so factor in waiting time. It's very filling, so a small slice can go a long way!
Visit Navy Pier, a historic landmark stretching into Lake Michigan. It offers a wide array of entertainment, including the Centennial Wheel, gardens, shops, restaurants, and boat tours. It's a lively spot for families and provides great views of the city.
Tip: Consider a sightseeing boat tour from Navy Pier for a different perspective of the skyline.
Aboard
Le Bellot for Tauck
From
Chicago, Illinois
2 Sailings
Sep 1 - Sep 15, 2026
Published prices from
per person*
taxes & fees included
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