easy
2–3 hours
Suitable for most fitness levels; primarily urban walking on sidewalks and indoor venues
Venture beneath Chicago’s streets and beyond its skyline with Inside Chicago Walking Tours. Uncover the city’s architectural marvels, secret interiors, and dark histories on expertly crafted trips through the Loop and beyond.
Most tours involve several hours of walking on city streets and interior spaces; sturdy shoes will keep your feet happy.
Chicago’s weather can shift quickly, so carry water and dress in layers to stay comfortable on outdoor segments.
Arriving 10-15 minutes early ensures smooth check-in and allows time to ask questions before the tour begins.
Guides encourage active participation, so bring curiosity—it enriches your experience and uncovers more local stories.
Chicago’s Loop developed rapidly after the Great Fire of 1871 and became a laboratory for architectural innovation, particularly the skyscraper.
Tours emphasize preserving historic architecture and promoting responsible urban tourism that respects interior spaces and local communities.
Supportive footwear is a must for navigating paved city streets and building interiors.
Layering helps adjust to Chicago’s variable weather between indoor and outdoor environments.
all specific
Stay hydrated during tours, especially in warmer months or longer sessions.
spring|summer|fall specific
Spring and fall rains can be sudden; light rain gear keeps your tour on track.
spring|fall specific