Discover Chicago’s dynamic neighborhoods, iconic landmarks, and hidden gems with a flexible, private city tour tailored to your schedule. Whether it’s a quick stopover or a full-day immersion, see the Windy City through the eyes of a local guide.
More ways to explore the area's outdoor wonders
Chicago’s streets hum with the rhythm of a city both historic and relentlessly modern. Imagine stepping aboard a private tour vehicle that glides through downtown, the iconic skyline daring you to look up, as towering skyscrapers reflect Lake Michigan’s shifting moods. From intimate neighborhoods to celebrated landmarks, Chicago City Tours unspools the city’s story through a private, customizable journey ranging from 2 to 8 hours, perfect for those pressed for time or hungry for a deep dive.
Difficulty
easy
Duration
2–8 hours
Fitness Level
Suitable for all fitness levels; minimal walking required but some standing and short strolls included.
Wildlife
History
Chicago’s rebuild after the 1871 Great Fire reshaped it into a powerhouse of architecture and culture, a legacy visible in its skyline and neighborhoods.
Conservation
Chicago promotes sustainable urban tourism by encouraging use of public transportation and supporting green spaces like Grant Park and the Riverwalk.
Reserve your spot on the Chicago City Tours today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Dress in layers for variable weather
Chicago's lakefront climate can change rapidly; pack and wear flexible layers to stay comfortable throughout your tour.
Wear comfortable shoes
Some walking is included around key sites, so sturdy, comfortable footwear will make your experience more enjoyable.
Plan your timing with traffic in mind
Allow extra time during rush hours as downtown traffic can slow travel; your guide will help optimize your route accordingly.
Bring a portable charger for your devices
With photo opportunities at every turn and digital ticketing, keeping your phone powered ensures seamless use.
Layered Clothing
Allows comfort through Chicago’s rapidly shifting urban weather.
Comfortable Walking Shoes
Needed for short walks around city landmarks and neighborhoods.
Sunglasses
Protects eyes during bright summer days on the riverwalk or parks.
summer
Portable Phone Charger
Ensures your devices stay powered for photos and navigation throughout the tour.