10. Old Route 66 – Illinois old Route 66 – Chicago old Route 66
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- Historic Route 66 Begin Sign
- Berghoff Restaurant
- W Chicago – City Center W Hotel (former Midland Hotel)
- Chicago River bridge
- Union Station (Beaux-Arts)
- Lou Mitchell’s Restaurant
- Hotel Chicago (former Rosemoor Hotel)
- Ogden Avenue
- Former Mercury Oil gas station
- Castle Car Wash
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9. Pullman National Historical Park (Pullman Neighborhood)
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- Pullman Administration Building
- North Wing Factory
- Rear Erecting Shops
- Hotel Florence
- Market Hall
- Stable Building
- Greenstone United Methodist Church
- Pullman Fire Station
- Pullman Wheel Works
- A. Philip Randolph Pullman Porter Museum
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8. Chicago neighborhoods
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- The Loop (see below)
- Most of Chicago’s highest buildings (see Chicago Skyline below)
- Early Chicago Skyscrapers (World Heritage Tentative List)
- Millennium Park
- Grant Park
- Art Institute of Chicago
- River North-Streeterville
- Michigan Avenue’s Magnificent Mile
- Navy Pier
- John Hancock Center (875 North Michigan Avenue)
- The Wrigley Building
- Historic Water Tower
- Hyde Park
- Site of the 1893 World’s Columbian Exposition (Chicago World’s Fair – Jackson Park, including the Museum of Science and Industry)
- Frank Lloyd Wright’s Frederick C. Robie House (see below)
- University of Chicago (Institute for the Study of Ancient Cultures: West Asia & North Africa – formerly the Oriental Institute, Smart Museum of Art, and the Joe and Rika Mansueto Library)
- Former residence of President Barack Obama and the Obama Kissing Rock at 53rd Street-Dorchester Avenue memorializing where Barack and Michelle Obama shared their first kiss
- Powell’s Books Chicago
- Old Town
- The Second City
- The Spice House
- The Fudge Pot
- Bronzeville
- Louis “Satchmo” Armstrong Home
- Ida B. Wells-Barnett House
- Harold Washington Cultural Center
- Chinatown
- Chinatown Square
- Old Chinatown
- Chinese-American Museum of Chicago
- Pilsen (Mexican-American neighborhood)
- National Museum of Mexican Art
- Thalia Hall
- 16th Street Murals
- Logan Square
- Logan Square Park
- Kedzie Boulevard
- Palmer Square Park
- Edgewater
- Bryn Mawr Historic District
- Chicagoland Games: Dice Dojo
- Raven Theatre
- Rogers Park
- Lifeline Theatre
- Loyola Park
- Loyola Beach
- The Loop (see below)
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7. Chicago Lakefront and Chicago River
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- Navy Pier
- Chicago Architecture Boat Tour
- Chicago Riverwalk
- Chicago Portage National Historic Site
- Illinois and Michigan Canal National Heritage Corridor
- Chicago Harbor Lighthouse
- Chicago Water Taxi
- Northerly Island
- Lake Michigan harbors
- Lake Michigan beaches
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6. Frank Lloyd Wright Architecture (World Heritage Site)
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- Oak Park Home and Studio (Oak Park; part of World Heritage Site)
- Unity Temple (Oak Park; part of World Heritage Site)
- Frederick C. Robie House (Hyde Park; part of World Heritage Site)
- The Rookery Building’s Light Court (The Loop)
- Emil Bach House (Rogers Park)
- Wright Around Chicago Tour
- Wright Around Oak Park Tour
- Pedal Oak Park Tour
- Wright Plus Architectural Housewalk Special Tour
- Wright in the Region Day Trip (Milwaukee)
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5. Chicago’s museums
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- Field Museum
- Art Institute of Chicago
- Museum of Science and Industry (former Palace of Fine Arts – 1893 World’s Columbian Exposition)
- Shedd Aquarium
- Adler Planetarium
- Chicago Water Tower Art Gallery
- National Museum of Mexican Art
- Chinese-American Museum of Chicago
- Oriental Institute Museum
- DuSable Museum of African American History
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4. Grant Park
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- President’s Court – Abraham Lincoln: The Head of State (Illinois is the Land of Lincoln), Art on the Farm Urban Agriculture Potager Kitchen Garden, and Artists and Automobiles
- Congress Plaza – Sir Georg Solti Garden, Eagle Fountains, Daphne sculpture, The Bowman sculpture, The Spearman sculpture, and Spirit of Music Garden
- Buckingham Fountain (the eastern terminus of old Route 66)
- Petrillo Music Shell and Butler Field
- North and South Rose Gardens
- Formal Gardens, Grant Bark Park, and Grant Skate Park
- Hutchinson Fields and Statue of Christopher Columbus
- Lakefront Park and Queen’s Landing
- Monroe Harbor and Chicago Yacht Club
- Maggie Daley Park – Rock Climbing, Skating Ribbon, Children Playground, Cancer Survivors’ Garden, Peanuts Park Tennis Courts
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3. Millennium Park
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- Millennium Monument and Wrigley Square
- Boeing Gallery
- Chase Promenade
- Harris Theater
- McCormick Tribune Plaza (seasonal ice rink)
- Cloud Gate “The Bean”
- Jay Pritzker Pavilion and Great Lawn
- Crown Fountain
- Lurie Garden
- BP Pedestrian Bridge
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2. Early Chicago Skyscrapers (World Heritage Tentative List)
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- Auditorium Theatre Building
- Second Leiter Building
- Marquette Building
- Rookery Building
- Monadnock Building
- Old Colony Building
- Ludington Building
- Fisher Building
- Schlesinger & Mayer Building (Sullivan Center)
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1. Chicago Skyline
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- Sears Tower (Willis Tower – The Loop)- 1,451′; 3rd-tallest building in the United States; 26th-tallest building in the world; tallest building in the world: 1974-1998)
- Tribune East Tower (Streeterville – under construction – 2027)- 1,422′
- International Hotel and Tower (Streeterville) – 1,388′
- St. Regis Chicago (Vista Tower – The Loop) – 1,191′
- Aon Center (The Loop) – 1,136′; formerly known as the Standard Oil Building; tallest building in Chicago: 1973-1974
- John Hancock Center (875 North Michigan Avenue – Streeterville) – 1,127′; tallest building in Chicago: 1969-1973
- One Chicago Square (River North) – 1,011′
- Franklin Center (AT&T Corporate Center – The Loop) – 1,007′
- Richard J. Daley Center (The Loop) – 648′; tallest building in Chicago: 1965-1969
- Chicago Board of Trade Building (The Loop) – 605′; tallest building in Chicago: 1930-1965
- Chicago Temple Building (The Loop) – 568′; tallest building in Chicago: 1924-1930
- The Wrigley Building (Streeterville) – 425′; tallest building in Chicago: 1922-1924
- Six North Michigan Avenue (The Tower Building; Montgomery Ward & Company Building – The Loop) – 282′; tallest building in Chicago: 1899-1922
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