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Itinerary
Day 1 | Journey to Chicago
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
Our adventure begins as we board our comfortable coach and travel towards the U.S. border, enjoying scenic views along the way. After a quick stop at Duty-Free, we continue our journey into the United States, making our way to Chicago. Along the route, you'll have time to relax, socialize, and prepare for the exciting days ahead. In the evening, we arrive at our luxurious hotel just outside downtown Chicago. The rest of the night is yours to explore at your own pace or simply unwind after a day of travel.
Day 2 | Discovering Chicago’s Treasures
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
Get ready to explore some of Chicago's most iconic sights and hidden gems. We begin our day with a visit to a stunning city landmark, where you can capture breathtaking photos against the backdrop of Lake Michigan. As we move through the city, we’ll discover architectural marvels, historic neighborhoods, and iconic sports venues. A scenic drive takes us along the city’s famous waterfront, leading to a historic pier filled with shops, attractions, and picturesque views. In the evening, indulge in a true Chicago experience at one of the city’s oldest and most beloved Italian restaurants, where you’ll enjoy exceptional food and vibrant local culture.
DAY 3 | Exploring Chicago’s Icons and Hidden Gems
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
Our third day in Chicago is all about discovery and delight. We start with a stroll through a beautifully designed urban park, famous for its stunning sculptures and lush gardens. Next, we explore a historic building with rich cultural significance before taking a scenic drive through the heart of the city. You’ll have free time to explore one of Chicago's premier shopping districts, where luxury boutiques and charming cafes await. In the evening, we regroup for a final dinner stop at a popular local dining hub before heading back to the hotel.
DAY 4 | Return to Toronto
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
After a hearty breakfast, we begin our journey back to Toronto, reflecting on the memories created over the past few days. Along the way, we'll stop for a bit of shopping at one of the largest outlet malls in the region. As we continue, there will be time for breaks and refreshments, ensuring a comfortable and enjoyable trip home. We expect to arrive back in Toronto by evening, with drop-offs at the same locations where our journey began.
Frequently Asked Questions
Is this tour suitable for seniors?
Yes! Our 4-day Chicago tour is designed with comfort and ease in mind. Guests enjoy premium coach travel, a centrally located hotel, and a relaxed, guided itinerary. Many of our travelers are seniors, and we ensure everyone feels welcome and supported throughout the journey.
What’s included in the Chicago tour?
This fully guided tour includes round-trip transportation from Toronto, a 3-night hotel stay, and immersive sightseeing experiences in Chicago. Highlights include:
- Guided architectural cruise on the Chicago River
- Visits to Millennium Park, the Magnificent Mile, and historic neighborhoods
- Free time to enjoy deep-dish pizza, cultural attractions, and shopping
- Live entertainment and optional evening outings
Our professional guides provide rich local insights, making your experience effortless and unforgettable.
Where are the pickup locations?
We offer multiple convenient pickup points across the Greater Toronto Area, including Scarborough, Etobicoke, and Mississauga. Exact details are provided in your confirmation email and listed on the tour page. Please arrive 15 minutes early.
How much walking is involved?
The tour includes moderate walking during sightseeing, riverfront stops, and local exploration. We maintain a comfortable pace and include breaks. If you require additional support, our team is here to help.
Are meals included?
Hotel breakfasts are included daily. The rest of your meals are flexible, allowing you to enjoy Chicago’s world-famous food scene — from deep-dish pizza to global cuisine — at your own pace.
Is there a restroom on the bus?
Yes — our modern coach buses are equipped with onboard restrooms for your comfort during the drive.
Can I join this tour solo?
Absolutely! Many of our guests travel solo. Our tours are welcoming and social, so you’ll feel part of the group right from the start.