Iconic Chicago Bus Tours from Toronto

Culture & history Tours Culinary & nightlife Multi-day trips Landmarks & monuments Activities Good for groups Activities for couples Small group activities Solo travelers' tours Rainy-day activities Architecture Garden & park tours

Embark on an exciting journey with us as we travel from Toronto to the vibrant heart of Chicago, one of America's most dynamic urban landscapes.

Our Top Experiences and Tours in Chicago:
If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!
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Highlights

  • Fully Narrated Two-Day Sightseeing Tours of Chicago
  • Three-night stay in a luxurious hotel
  • A pre-set dinner at the historic Italian Village, established in 1927
  • Three hotel breakfasts
  • Escorted Visit of Chicago Cultural Center State Street Walking Tour

Description

Experience Iconic Chicago on a Bus Tour from Toronto From the iconic skyline to the serene shores of Lake Michigan, Chicago is not just America's cleanest big city—it's also one of the friendliest. Our bus tours from Toronto offer a seamless way to explore Chicago’s world-class architecture, pristine beaches, and hidden gems like the University of Chicago, where Barack and Michelle Obama first met. Plus, you’ll get an exclusive look at the nearly completed Obama Presidential Center! Indulge in Chicago’s Culinary Delights No trip to Chicago is complete without indulging in its culinary delights. Join us for an unforgettable meal at the legendary Italian Village, the city’s oldest and most beloved Italian restaurant, proudly family-owned for four generations. Why Choose Our Holiday Bus Tours from Toronto? Explore the vibrant city of Chicago with our expertly curated, family-friendly bus tours. Whether you’re planning a quick getaway or a longer holiday, our tours offer a stress-free, guided experience that caters to all ages—including solo travelers. Ready to Explore Chicago? Book Your Bus Tour from Toronto Today! Don't miss out on this incredible opportunity to visit Chicago with Cranberry Tours. Secure your adventure now with a 15% deposit and start your journey to the Windy City. Limited spots are available, so book your holiday bus tour from Toronto today!

Includes

Fully Narrated Two-Day Sightseeing Tours of Chicago Escorted Visit of Chicago Cultural Center State Street Walking Tour Scenic Drive Through Chicago’s Landmarks A pre-set dinner at the historic Italian Village, established in 1927 (included in your tour). Additional menu items are available at extra cost. Three-night stay in a luxurious hotel conveniently situated in a serene Chicago suburb hotel it's just a stone's throw from the bustling downtown area Three hotel breakfasts Round-trip travel in climate-controlled, comfy coach bus

Easy cancellation

Cancel up to 24 hours in advance for a full refund

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