Chicago Bus Tour from Toronto – 4 Days of Iconic City Vibes
$1,249 CAN
💵 Price per person ✔️ Taxes included
🛏️ Double occupancy
💼 Solo traveller rate: $1,399
The City Is Calling — Are You Coming?
Get swept away by the skyline, the sounds of jazz, and the irresistible energy of Chicago. On this fully guided 4-day bus tour from Toronto, you’ll experience the best of the Windy City — from Millennium Park to the Magnificent Mile — with deluxe coach travel, premium hotel stays, and zero planning stress.
✨ Discover more luxury guided bus tours from Toronto to exciting North American cities.
Upcoming Tour Dates
What's Included?
✅ Tap to Expand
Fully Guided Two-Day Sightseeing Tour
Explore Chicago’s top landmarks with expert narration and local insights along the way.
Visit to the Chicago Cultural Center
Discover the rich history and stunning architecture of this beloved Chicago landmark.
State Street Walking Tour
Stroll one of Chicago’s most famous streets, lined with shops, stories, and culture.
Scenic Drive
Enjoy a comfortable ride through Chicago’s most iconic neighborhoods and skyline views.
Dinner at the Historic Italian Village
Savor a pre-set meal at Chicago’s oldest Italian restaurant, established in 1927.
Three-Night Stay at a Luxurious Suburban Hotel
Relax at a premium hotel just minutes from downtown Chicago — quiet, comfortable, and convenient.
Daily Hotel Breakfast
Start each morning with a full breakfast, included with your stay.
Round-Trip Coach Travel from Toronto
Travel in comfort aboard a climate-controlled coach bus with friendly staff and smooth logistics.
What's Included?
🎯 Fully Guided Two-Day Sightseeing Experience
Explore Chicago’s top attractions with a friendly local guide. Hear the stories, snap the sights, and soak in the skyline.
🏛 Visit to the Chicago Cultural Center
Marvel at the historic architecture and discover one of Chicago’s most beloved cultural gems.
🚶♀️ State Street Walking Tour
Wander Chicago’s legendary State Street — filled with shops, stories, and signature city energy.
🚌 Scenic City Drive
Enjoy a panoramic drive through Chicago’s famous neighborhoods, with stunning skyline views along the way.
🍽 Dinner at the Historic Italian Village
Dine at Chicago’s oldest Italian restaurant, serving tradition since 1927. (Gratuity included.)
🛏 3-Night Stay at a Premium Suburban Hotel
Unwind in a modern, quiet hotel just outside the city — the perfect place to rest after your urban adventures.
🍳 Daily Hot Breakfast
Start each day with a full breakfast included at your hotel.
🚍 Round-Trip Coach Travel from Toronto
Relax on a climate-controlled coach with friendly staff, smooth logistics, and scenic travel.
Tour Itinerary
Day 1: Toronto → Chicago
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
6:30 AM – 11:00 AM: Begin your adventure as you board the coach at your selected pick-up location. We’ll travel toward the Sarnia Canada/U.S. border, with a coffee break along the way.
11:30 AM: Stop at Duty-Free before crossing into the U.S. (Have your travel documents ready for U.S. entry).
1:30 PM – 2:30 PM: Restroom break en route to Chicago.
5:00 PM – 6:00 PM: Dinner break (meals not included).
8:00 PM: Arrive at your luxurious hotel in a Chicago suburb. Enjoy the rest of your evening at leisure.
Day 2: Discovering Chicago’s Artistic and Architectural Treasures
8:00 AM: Depart the hotel for Buckingham Fountain.
8:45 AM: Photo stop at the iconic 1927 fountain overlooking Lake Michigan.
9:15 AM: Scenic drive along Chicago’s sandy beaches, arriving at Wrigley Field for an hour of independent exploration.
10:15 AM: Drive through the Gold Coast and Inner Lake Shore Drive, with a photo stop at the Mies van der Rohe-designed apartments.
11:30 AM: Arrive at the Michigan Avenue Bridge for an optional Architecture River Cruise (cost not included).
1:45 PM: Head directly to Navy Pier.
2:00 PM – 4:00 PM: Free time to explore Navy Pier’s attractions, restaurants, and breathtaking lake views.
4:00 PM: Board the bus for Museum Campus, with a stop at Planetarium Point for stunning skyline views.
4:15 PM: Walking tour of State Street, featuring historic landmarks like the former Marshall Field's (now Macy's) and the Carson Pirie Scott building.
5:30 PM: Dinner at Italian Village – Chicago’s oldest and finest Italian restaurant. Enjoy special seating, a wine discussion by the wine director, and view the Tuscany-inspired mural by artist Nancy Wright Gelband.
8:00 PM – 8:15 PM: Depart for the hotel.
9:00 PM: Approximate arrival back at the hotel.
Day 3: Chicago’s Iconic Landmarks & Hidden Gems
8:00 AM: Depart the hotel for a full day of exploration.
8:45 AM: Brief stop at the United Center for photos.
9:15 AM: Depart for Millennium Park – Chicago's top attraction.
9:45 AM – 10:30 AM: Guided walking tour of Millennium Park, featuring Cloud Gate (The Bean), Pritzker Pavilion, and Crown Fountain.
11:30 AM: Visit the Chicago Cultural Center for a 30-minute escorted tour.
12:00 PM: Scenic drive through The Loop, showcasing the Riverwalk, Willis Tower, Wrigley Building, and Tribune Tower.
12:20 PM – 4:00 PM: Free time at Water Tower Place for upscale shopping and dining.
5:00 PM: Begin the return journey.
5:45 PM – 6:00 PM: Dinner break at Oak Brook Center. Enjoy independent dining before reboarding the bus.
8:00 PM: Return to the hotel.
Day 4: Chicago → Toronto
6:30 AM – 7:30 AM: Enjoy breakfast at the hotel (included) before checkout.
7:30 AM: Depart for the journey back to Toronto.
10:00 AM: Coffee break along the way.
2:00 PM – 4:00 PM: Stop at Prime Outlet Mall in Birch Run, Michigan for shopping and lunch.
4:00 PM: Continue toward the border.
6:00 PM: Coffee break before the final stretch.
7:30 PM – 9:30 PM: Arrive back in Toronto at your original pick-up location.
🚍 Easy Pick-Up Options Across the GTA
Start your Chicago adventure with ease! We offer several convenient pick-up points throughout the Greater Toronto Area, making it simple to hop aboard your 4-day guided bus tour to Chicago. Just choose the location that works best for you — and let the journey begin.
🌆 Your Next Great Escape Starts Here
Join us on a 4-day guided adventure to the Windy City, filled with iconic sights, great food, and unforgettable moments — all from the comfort of a deluxe coach.
✅ Limited seats available
✅ Perfect for seniors and solo traveler
✅ Fully guided, no hidden fee
Chicago Bus Tour from Toronto –
4 Days of Iconic City Vibes
$1,249 CAN
💵 Price per person ✔️Taxes included
🛏️ Double occupancy
💼 Solo traveller rate: $1,399
📅 Tour Dates
Oct 10-13, 2025
The City Is Calling — Are You Coming?
Get swept away by the skyline, the sounds of jazz, and the irresistible energy of Chicago. On this fully guided 4-day bus tour from Toronto, you’ll experience the best of the Windy City — from Millennium Park to the Magnificent Mile — with deluxe coach travel, premium hotel stays, and zero planning stress.
✨ Discover more luxury guided bus tours from Toronto to exciting North American cities.
What's Included?
🎯 Fully Guided Two-Day Sightseeing Experience
Explore Chicago’s top attractions with a friendly local guide. Hear the stories, snap the sights, and soak in the skyline.
🏛 Visit to the Chicago Cultural Center
Marvel at the historic architecture and discover one of Chicago’s most beloved cultural gems.
🚶♀️ State Street Walking Tour
Wander Chicago’s legendary State Street — filled with shops, stories, and signature city energy.
🚌 Scenic City Drive
Enjoy a panoramic drive through Chicago’s famous neighborhoods, with stunning skyline views along the way.
🍽 Dinner at the Historic Italian Village
Dine at Chicago’s oldest Italian restaurant, serving tradition since 1927. (Gratuity included.)
🛏 3-Night Stay at a Premium Suburban Hotel
Unwind in a modern, quiet hotel just outside the city — the perfect place to rest after your urban adventures.
🍳 Daily Hot Breakfast
Start each day with a full breakfast included at your hotel.
🚍 Round-Trip Coach Travel from Toronto
Relax on a climate-controlled coach with friendly staff, smooth logistics, and scenic travel.
Tour Itinerary
Day 1: Toronto → Chicago
NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.
6:30 AM – 11:00 AM: Begin your adventure as you board the coach at your selected pick-up location. We’ll travel toward the Sarnia Canada/U.S. border, with a coffee break along the way.
11:30 AM: Stop at Duty-Free before crossing into the U.S. (Have your travel documents ready for U.S. entry).
1:30 PM – 2:30 PM: Restroom break en route to Chicago.
5:00 PM – 6:00 PM: Dinner break (meals not included).
8:00 PM: Arrive at your luxurious hotel in a Chicago suburb. Enjoy the rest of your evening at leisure.
Day 2: Discovering Chicago’s Artistic and Architectural Treasures
8:00 AM: Depart the hotel for Buckingham Fountain.
8:45 AM: Photo stop at the iconic 1927 fountain overlooking Lake Michigan.
9:15 AM: Scenic drive along Chicago’s sandy beaches, arriving at Wrigley Field for an hour of independent exploration.
10:15 AM: Drive through the Gold Coast and Inner Lake Shore Drive, with a photo stop at the Mies van der Rohe-designed apartments.
11:30 AM: Arrive at the Michigan Avenue Bridge for an optional Architecture River Cruise (cost not included).
1:45 PM: Head directly to Navy Pier.
2:00 PM – 4:00 PM: Free time to explore Navy Pier’s attractions, restaurants, and breathtaking lake views.
4:00 PM: Board the bus for Museum Campus, with a stop at Planetarium Point for stunning skyline views.
4:15 PM: Walking tour of State Street, featuring historic landmarks like the former Marshall Field's (now Macy's) and the Carson Pirie Scott building.
5:30 PM: Dinner at Italian Village – Chicago’s oldest and finest Italian restaurant. Enjoy special seating, a wine discussion by the wine director, and view the Tuscany-inspired mural by artist Nancy Wright Gelband.
8:00 PM – 8:15 PM: Depart for the hotel.
9:00 PM: Approximate arrival back at the hotel.
Day 3: Chicago’s Iconic Landmarks & Hidden Gems
8:00 AM: Depart the hotel for a full day of exploration.
8:45 AM: Brief stop at the United Center for photos.
9:15 AM: Depart for Millennium Park – Chicago's top attraction.
9:45 AM – 10:30 AM: Guided walking tour of Millennium Park, featuring Cloud Gate (The Bean), Pritzker Pavilion, and Crown Fountain.
11:30 AM: Visit the Chicago Cultural Center for a 30-minute escorted tour.
12:00 PM: Scenic drive through The Loop, showcasing the Riverwalk, Willis Tower, Wrigley Building, and Tribune Tower.
12:20 PM – 4:00 PM: Free time at Water Tower Place for upscale shopping and dining.
5:00 PM: Begin the return journey.
5:45 PM – 6:00 PM: Dinner break at Oak Brook Center. Enjoy independent dining before reboarding the bus.
8:00 PM: Return to the hotel.
Day 4: Chicago → Toronto
6:30 AM – 7:30 AM: Enjoy breakfast at the hotel (included) before checkout.
7:30 AM: Depart for the journey back to Toronto.
10:00 AM: Coffee break along the way.
2:00 PM – 4:00 PM: Stop at Prime Outlet Mall in Birch Run, Michigan for shopping and lunch.
4:00 PM: Continue toward the border.
6:00 PM: Coffee break before the final stretch.
7:30 PM – 9:30 PM: Arrive back in Toronto at your original pick-up location.
🚍 Easy Pick-Up Options Across the GTA
Start your Chicago adventure with ease! We offer several convenient pick-up points throughout the Greater Toronto Area, making it simple to hop aboard your 4-day guided bus tour to Chicago. Just choose the location that works best for you — and let the journey begin.
🌆 Your Next Great Escape Starts Here
Join us on a 4-day guided adventure to the Windy City, filled with iconic sights, great food, and unforgettable moments — all from the comfort of a deluxe coach.
✅ Limited seats available
✅ Perfect for seniors and solo traveler
✅ Fully guided, no hidden fee
Frequently Asked Questions about Your Chicago Bus Tour
Is this tour suitable for seniors?
Yes! This 4-day guided tour to Chicago is thoughtfully designed with seniors in mind. With a relaxed pace, premium accommodations, and smooth coach travel, it's ideal for those seeking comfort and cultural enrichment. Many of our guests are also solo senior travelers.
What are the pickup spots for the tour?
We offer multiple convenient pickup locations in the Greater Toronto Area, including Scarborough, Etobicoke, and Mississauga. Full pickup details are confirmed 2–3 days before departure. Please arrive at your designated location at least 15 minutes early.
How much walking is involved?
Expect light to moderate walking during city tours and attractions. The itinerary includes regular breaks and a comfortable pace.
Is there a restroom on the bus?
Yes. All our luxury motorcoaches are equipped with onboard washrooms for your convenience during travel days.
How many bags can I bring?
Each guest may bring one suitcase (stored under the coach) and one small carry-on that fits in the overhead bin.
Will there be free time to explore?
Definitely! While we include guided tours in each city, you'll also enjoy free time to explore **Chicago's** vibrant downtown.
Can I join this tour solo?
Absolutely! Many of our guests travel solo and love the friendly, social atmosphere of our group tours. It’s a great way to meet people and share amazing memories.
🧳 First time joining a bus tour?
Our easy-to-follow Preparation Guide covers everything — from luggage tags and packing tips to hotel check-ins and daily routines.
📘 Visit the Tour Preparation Guide →