7 Ways to Experience the Chicago City Skyline

Chicago is famous for its stunning skyline, featuring iconic buildings like the Willis Tower (formerly the Sears Tower), the John Hancock Center, and other architectural marvels. Observation decks in these skyscrapers offer breathtaking views of the city, Lake Michigan, and the surrounding landscape. Here are some of the best observation decks and ways to explore the skyline:

1. Skydeck Chicago (Willis Tower)

• Location: 233 S Wacker Dr, Chicago, IL
• Height: 1,353 feet (412 meters)
• Highlight: The Skydeck is located on the 103rd floor of the Willis Tower, offering panoramic views of up to four states on clear days: Illinois, Indiana, Wisconsin, and Michigan.
• Features: The Ledge, a glass box that extends 4.3 feet out from the building, allows visitors to stand directly above the city streets, offering a heart-pounding perspective from 1,353 feet in the air.
• Best Time to Visit: Sunset or night for illuminated views of the skyline.

2. 360 CHICAGO Observation Deck (John Hancock Center)

• Location: 875 N Michigan Ave, Chicago, IL
• Height: 1,030 feet (314 meters)
• Highlight: Located on the 94th floor, 360 CHICAGO offers stunning views of Lake Michigan, Navy Pier, and the city’s North Side.
• Feature: TILT, a moving platform that tilts visitors outward from the building, provides a unique view of the streets below.
• Best Time to Visit: Daytime to appreciate the expanse of Lake Michigan and the surrounding neighborhoods.

3. Chicago Riverwalk and Boat Tours

• While observation decks give you an aerial view, a boat tour on the Chicago River offers a different way to admire the skyline. Popular boat tours like Shoreline Sightseeing Cruise Chicago or the Chicago Architecture Foundation Center River Cruise provide an up-close look at Chicago’s world-renowned architecture. Each cruise is accompanied by expert guides who explain the history and significance of the buildings.
• Chicago Riverwalk: Stretching along the south bank of the Chicago River, the Riverwalk is lined with parks, restaurants, and spots to enjoy views of the skyscrapers from the ground level.

4. Skyline Drive (Lake Shore Drive Chicago)

• If you prefer exploring the skyline from the ground, driving along Lake Shore Drive offers scenic views of both the city skyline and Lake Michigan. The stretch between downtown and the museum campus is particularly spectacular, with iconic landmarks like the Adler Planetarium and Shedd Aquarium providing great vantage points for photos.

5. Chicago Helicopter Tours

• For an unforgettable adventure, you can take a helicopter tour over the Chicago skyline. These tours provide a bird’s-eye view of the skyscrapers, Lake Michigan, and the city grid, with flights usually departing from Fly Heli Chicago. They offer day and night tours, with the night flights providing an enchanting view of the illuminated skyline.



6. Chicago Centennial Wheel

• Location: Navy Pier, 600 E Grand Ave, Chicago, IL
• While not as high as the observation decks, the Centennial Wheel at Navy Pier gives you a leisurely and rotating perspective of the city skyline, the lake, and Navy Pier itself. The wheel offers enclosed, temperature-controlled gondolas, making it accessible year-round.

7. Adler Planetarium Skyline Walk

• For a less crowded and relaxing view of the Chicago skyline, head to the Adler Planetarium at the edge of the Museum Campus. It offers one of the best ground-level vantage points of the skyline, especially during sunset. The combination of the lakefront and city lights creates a great setting for photos.

Tips for Exploring the Skyline:

• Best Time to Visit: To avoid crowds, weekday mornings are ideal. However, sunset is one of the most spectacular times for skyline views, especially from the Skydeck or 360 CHICAGO. Night views also offer a dazzling display of city lights.
• Weather Considerations: Clear days offer the best visibility from observation decks, but the fog can add a moody atmosphere to the skyline. Check weather conditions before heading out, especially for outdoor tours or observation decks.
• Photography Tips: Bring a wide-angle lens for expansive views and arrive early to secure a good spot, especially if you're aiming to capture the golden hour or the blue hour after sunset.