Small Group Chicago Tours and Attractions

Explore the Windy City and take in its beautiful architecture and booming arts and culture scene. - Walk through Chicago’s front door at the Buckingham Fountain , one of the largest fountains in the world.. - No trip to Chicago is complete without a stop at the Cloud Gate also known as the Chicago Bean, a public outdoor installation by artist Anish Kapoor, featured in many movies and television shows such as The Vow and Parks and Recreation. - Relax and take in the beautiful surrounding architecture with a Shoreline Architecture Cruise through the Chicago River.

FAQs

What are the top attractions I should visit on a tour in Chicago? 

When visiting Chicago, make sure to explore iconic landmarks like Cloud Gate (Chicago Bean), Skydeck Chicago and The Ledge, Buckingham Fountain, and take a Shoreline Architecture Cruise through the Chicago River. These experiences will give you a glimpse of the city's rich architecture and cultural heritage.

 

Which tour offers the best overview of Chicago's top sights? 

Our Best of Chicago Tour is designed to give you a comprehensive overview of the city's top attractions, including skyscrapers, waterfront areas, and vibrant arts and culture scenes. Don't miss out on this all-encompassing experience.

 

Is there a nighttime tour that showcases Chicago's beauty after dark? 

Yes, we offer the Scenic Chicago Night Tour, where you can witness the Windy City illuminated in all its glory. This tour provides a unique perspective of Chicago's lights and ambiance after the sun sets.

 

Can I book a private tour of Chicago for a more exclusive experience? 

Absolutely! Our Private Tour of Chicago allows you to tailor the experience to your preferences and explore the city's best attractions at your own pace. It's the perfect option for a personalized and exclusive adventure.

 

Are there any walking tours available for those who prefer exploring on foot? 

Certainly! Our Best of Chicago Walking Tour is an excellent option for those who enjoy discovering a city on foot. You'll get to explore the Windy City's streets and neighborhoods up close.

 

What types of tours are available in Chicago? 

In Chicago, we offer a variety of tours, including day tours and multi-day tours. Whether you have a few hours or several days to explore the city, we have options to suit your schedule.

 

How can I book a tour with Tripshepherd in Chicago? 

To book a tour in Chicago, simply visit our Tours page and select the one that interests you. Click on the tour to view more details and pricing, then follow the easy booking process to secure your spot.