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!
530 Progress Ave, 530 Progress Ave, Toronto, ON M1P 2K2, Canada
6:30 AM Scarborough Scarborough Town Centre, LA-Z Boy Furniture Parking Lot.
This activity ends back at the meeting point.
6:30 AM - 11:00 AM Embark on your journey by boarding the coach at your selected pick-up location (departure times may vary). We'll head to the Sarnia Canada/U.S. border, so ensure you have your essential documents for compliance with U.S. entry laws. Along the way, enjoy a revitalizing coffee break. 11:30 AM Arrive at the duty-free haven, offering time for shopping and a leisurely lunch. Following this, we'll cross the border. 1:30 PM - 2:30 PM A brief restroom break en route. 5:00 PM - 6:00 PM We'll make a dinner stop en route (please note that dinner expenses are not included). 8:00 PM Anticipate reaching your luxurious hotel, nestled in a Chicago suburb just a stone's throw away from downtown. The evening is yours to relish at your leisure.
Duration: 10 hours
7:00 AM - 8:00 AM Kickstart your day with a satisfying breakfast provided at your hotel. 8:00 AM Our journey begins as the bus departs from the hotel. 9:00 AM - 3:00 PM Immerse yourself in a fully-guided city tour of Chicago led by a knowledgeable local guide. This comprehensive tour comprises a blend of bus and walking exploration.
Duration: 6 hours
The Magnificent Mile is a prestigious section of Chicago's Michigan Avenue, running from the Chicago River to Oak Street in the Near North Side. Renowned for its vibrant atmosphere, the Magnificent Mile is a top destination for shopping, dining, and entertainment, featuring luxury retailers, historic landmarks like the Water Tower, upscale hotels, and impressive skyscrapers. This iconic boulevard is also the heart of Chicago's annual holiday celebrations, including the Magnificent Mile Lights Festival, which illuminates the area with a stunning display of lights.
Millennium Park is a modern, lively gathering spot located in the heart of downtown Chicago. Known for its cutting-edge art, architecture, and landscape design, the park is home to the famous reflective sculpture "Cloud Gate," also known as "The Bean," which has become an iconic image of the city. It also features the Crown Fountain, an interactive work of public art, and the Jay Pritzker Pavilion, a bandshell designed by architect Frank Gehry that hosts free concerts and events. Stretching over 24.5 acres, Millennium Park is a green oasis in the urban landscape, offering residents and visitors alike a space for cultural activities, relaxation, and scenic city views.
Water Tower Place is a large urban, mixed-use development located in Chicago along the Magnificent Mile, notable for its 74-story skyscraper. It features a shopping mall with numerous high-end stores, boutiques, and restaurants, making it a popular destination for both shopping and dining. The building is also significant for being one of the few structures to survive the Great Chicago Fire in 1871, and the historic Water Tower adjacent to it is a symbol of old Chicago's resilience. Water Tower Place provides not just retail therapy but also houses residential units and a hotel, offering luxurious accommodations with spectacular views of the city and Lake Michigan.
Grant Park, known as "Chicago's front yard," is a sprawling urban park in the city's central business district, bordered by Lake Michigan to the east. It's a cultural hub that hosts major city events such as Taste of Chicago, Lollapalooza, and the Chicago Jazz Festival. The park is famous for its beautifully manicured landscapes, impressive fountains like Buckingham Fountain, and numerous public artworks. Spanning over 300 acres, Grant Park offers ample green space for recreation, sports, and leisure, and is also the site of the Art Institute of Chicago and Millennium Park, which lies within its northwestern corner. This scenic park provides residents and visitors with a serene escape from the urban bustle and panoramic views of the city skyline.
Navy Pier is a beloved Chicago landmark jutting out into Lake Michigan, known for its vibrant atmosphere and family-friendly attractions. Originally opened in 1916 as a shipping and recreational facility, it has since evolved into a popular entertainment hub. 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 ample park areas, gardens, shops, restaurants, and seasonal festivals, Navy Pier provides a lively and scenic experience for visitors of all ages. It's also a favored spot for fireworks, boat tours, and cultural events, making it a cornerstone of Chicago's recreational and tourism activities.
Duration: 1 hour
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 make a 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.
Duration: 12 hours
Toronto, Ontario
Toronto, Ontario
Toronto, Ontario
Toronto, Ontario
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