Chicago

Top Things to Do in Chicago: A Walkable Route of Must-See Spots

You can let GeoQuestr guide you through the city as you learn more about these amazing places along the way.

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The Windy City is a masterclass in architecture, culture, and lakefront beauty. Below is a route-style list of stops you can follow through downtown and along the waterfront.

1. Millennium Park & Cloud Gate — Start Here

Begin at Millennium Park, home to Cloud Gate (aka "The Bean"), the Jay Pritzker Pavilion, and the Crown Fountain. It's the centerpiece of downtown Chicago.

Why it's worth it:

• Cloud Gate's reflections are endlessly photogenic
• The Lurie Garden is a peaceful hidden section most people miss
• Free concerts and events happen regularly in the Pritzker Pavilion

2. Art Institute of Chicago — World-Class Art Next Door

Right on the edge of Millennium Park, the Art Institute of Chicago is one of the oldest and largest art museums in the United States. The collection spans 5,000 years.

What to do here:

• Grant Wood's "American Gothic" and Seurat's "A Sunday Afternoon" are here
• The Impressionist collection is one of the best outside France
• The Modern Wing has great city views from inside

3. Chicago Riverwalk — Architecture from Water Level

Head to the Chicago Riverwalk, a pedestrian path along the Chicago River that puts you at eye level with some of the world's most famous buildings.

Don't miss:

• The architecture boat tour is often called the best tour in any American city
• Walking the Riverwalk is free and gives you a different perspective on the skyline
• Multiple restaurants and bars line the path

4. Magnificent Mile — The Grand Boulevard

Walk north along Michigan Avenue's Magnificent Mile, Chicago's premier shopping and architecture street. The historic Water Tower survived the Great Chicago Fire of 1871.

Good mini-plans:

• The Wrigley Building and Tribune Tower are architectural standouts
• The Water Tower is one of the few buildings that survived 1871
• Navy Pier is at the east end if you want to extend the walk

5. Lincoln Park & Zoo — Free Zoo in the City

Head north to Lincoln Park, home to one of the last free zoos in the country, beautiful gardens, and the lakefront trail.

Why people love it:

• Lincoln Park Zoo has been free since 1868
• The conservatory has tropical plants year-round
• The lakefront trail connects all the way to the South Side

6. Willis Tower Skydeck — See It All From Above (Add-On)

If you want a birds-eye view, the Willis Tower Skydeck (formerly Sears Tower) puts you on a glass ledge 412 meters above the street.

Best for:

• The glass floor "Ledge" extends over the street below
• Clear days offer views across four states
• Sunset visits are spectacular

Simple Day Plan (Works for Most Visitors)

1. Millennium Park & Cloud Gate (morning)
2. Art Institute of Chicago (mid-morning)
3. Chicago Riverwalk (lunch + walk)
4. Magnificent Mile (afternoon)
5. Lincoln Park & Zoo (late afternoon)
6. Optional: Willis Tower Skydeck (sunset)

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