Join Cranberry Tours for an unforgettable bus journey from Toronto to Chicago. Explore iconic landmarks, shop the Magnificent Mile, and savor deep-dish pizza.
Toronto » Chicago
Chicago - 6:30 AM - 11:00 AM Begin your adventure by boarding the coach at your chosen pick-up spot (departure times may vary). We’ll head towards the Sarnia Canada/U.S. border, so make sure you have the necessary documents for U.S. entry. Enjoy a refreshing coffee break along the way.
11:30 AM Arrive at the duty-free area, allowing time for shopping and a relaxed lunch. Afterward, we’ll cross the border.
1:30 PM - 2:30 PM A quick restroom break during the journey.
5:00 PM - 6:00 PM We’ll stop for dinner en route (note that dinner costs are not included).
8:00 PM Expect to arrive at your luxurious hotel, located in a Chicago suburb close to downtown. The evening is yours to enjoy at your leisure.
Exploring Chicago
Chicago - 7:00 AM - 8:00 AM Start your day with a hearty breakfast provided at your hotel.
8:00 AM The bus departs from the hotel to begin our journey.
9:00 AM - 3:00 PM Experience a fully-guided city tour of Chicago led by an expert local guide. This extensive tour includes both bus and walking segments.
The Magnificent Mile - The Magnificent Mile is a prestigious stretch of Chicago’s Michigan Avenue, extending from the Chicago River to Oak Street in the Near North Side. Known for its lively atmosphere, the Magnificent Mile is a prime spot for shopping, dining, and entertainment, featuring luxury retailers, historic landmarks like the Water Tower, upscale hotels, and towering skyscrapers. This iconic boulevard is also the center of Chicago’s annual holiday celebrations, including the Magnificent Mile Lights Festival, which lights up the area with a dazzling display.
Millennium Park - Millennium Park is a vibrant, modern gathering place in the heart of downtown Chicago. Famous for its innovative art, architecture, and landscape design, the park is home to the renowned reflective sculpture “Cloud Gate,” also known as “The Bean,” an iconic symbol of the city. It also features the Crown Fountain, an interactive public art piece, and the Jay Pritzker Pavilion, a bandshell designed by architect Frank Gehry that hosts free concerts and events. Spanning 24.5 acres, Millennium Park offers a green oasis in the urban landscape, providing a space for cultural activities, relaxation, and scenic city views.
Water Tower Place - Water Tower Place is a major urban, mixed-use development along the Magnificent Mile, notable for its 74-story skyscraper. It includes a shopping mall with numerous high-end stores, boutiques, and restaurants, making it a popular destination for shopping and dining. The building is also significant for being one of the few structures to survive the Great Chicago Fire of 1871, and the historic Water Tower next to it is a symbol of old Chicago’s resilience. Water Tower Place offers not just retail therapy but also houses residential units and a hotel, providing luxurious accommodations with stunning views of the city and Lake Michigan.
Grant Park - Grant Park, often called “Chicago’s front yard,” is a vast urban park in the city’s central business district, bordered by Lake Michigan to the east. It’s a cultural hotspot that hosts major city events like Taste of Chicago, Lollapalooza, and the Chicago Jazz Festival. The park is renowned for its beautifully maintained landscapes, impressive fountains like Buckingham Fountain, and numerous public artworks. Covering over 300 acres, Grant Park offers ample green space for recreation, sports, and leisure, and is also home to the Art Institute of Chicago and Millennium Park, which is located in its northwestern corner. This scenic park provides a peaceful escape from the urban hustle and offers panoramic views of the city skyline.
Chicago Navy Pier & Downtown
Navy Pier - Navy Pier is a cherished Chicago landmark extending into Lake Michigan, known for its lively atmosphere and family-friendly attractions. Originally opened in 1916 as a shipping and recreational facility, it has since become a popular entertainment destination. Navy Pier features a 196-foot Ferris wheel offering panoramic views of the city skyline and the lake, the Chicago Children’s Museum, a grand IMAX theater, and the Chicago Shakespeare Theater. With its expansive park areas, gardens, shops, restaurants, and seasonal festivals, Navy Pier offers a vibrant and scenic experience for visitors of all ages. It’s also a favorite spot for fireworks, boat tours, and cultural events, making it a cornerstone of Chicago’s recreational and tourism activities.
Depart for home
Toronto - 6:30 AM - 7:30 AM Enjoy a hearty breakfast at the hotel (included) followed by the hotel check-out.
7:30 AM Depart from your Chicago hotel for the return journey to Toronto, taking in the picturesque scenic routes.
10:00 AM Take a coffee break en route.
2:00 PM - 4:00 PM We’ll stop at the Prime Outlet Mall (Birch Run Michigan) for shopping and lunch.
4:00 PM Depart for the border crossing (with the opportunity to shop duty-free).
6:00 PM Enjoy a coffee break en route.
7:30 PM - 9:30 PM Anticipate your expected arrival time, with the drop-off location being the same as your selected pick-up location.
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- Full Day Narrated Chicago Sightseeing
- Breakfast
- On-board restrooms
- Gratuities for the tour director and bus driver
Join Cranberry Tours for an exhilarating bus journey to the Windy City—Chicago! Our comfortable and scenic ride from Toronto will whisk you away to the heart of American urban culture. Upon arrival, immerse yourself in the architectural wonderland, with a planned itinerary including the towering Willis Tower, the historic Wrigley Building, and the art-filled expanses of Millennium Park. We’ll cruise down the Magnificent Mile for some world-class shopping and dine on authentic deep-dish pizza. With expert guides to lead the way, you’ll discover the rich tapestry of Chicago’s neighborhoods, each brimming with stories and local flavor. This tour promises not just sights and sounds but a deep dive into the vibrant spirit of one of America’s most iconic cities. Get ready for a Chicago adventure that will leave you with memories to last a lifetime!
- 5-12 Old (I.D. required), 0-4 Year Old (Not Permitted)
For a full refund, cancel at least 24 hours before the scheduled departure time.