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Experience Chicago

4 Days

 Sail the Chicago River, savor deep-dish pizza, and uncover architectural wonders.
🎯 Grab Your Spot Before It's Gone!        

  • Solo Traveler Rate

    Solo Traveler Rate


    $1398 CAN /Per Person

    Taxes Included


$ 1298 CAN  p / p

 ✅ Taxes included 🛏️ Double Occupancy

Your Chicago  Experience Includes:

  • Fully Guided Two-Day Sightseeing Tour: Explore Chicago’s top landmarks with expert narration along the way.
  • Visit to the Chicago Cultural Center: Discover the rich history and stunning architecture of this iconic landmark.
  • State Street Walking Tour: Stroll through one of Chicago’s most famous streets, lined with shops, history, and culture.
  • Scenic Drive: Enjoy a relaxing ride through Chicago’s most celebrated attractions and breathtaking skyline views.
  • Dinner at the Historic Italian Village: Savor a pre-set meal at Chicago’s oldest Italian restaurant, established in 1927. (Gratuity included, additional items available at extra cost.)
  • Three-Night Stay at a Luxurious Suburban Hotel: Relax in a peaceful, upscale hotel just minutes from Chicago’s vibrant downtown.
  • Daily Breakfast: Start each day with a delicious breakfast at the hotel, included in your package.
  • Comfortable Coach Bus Travel: Enjoy round-trip travel in a climate-controlled, comfortable coach bus from Toronto.
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About This Tour

Step into the vibrant rhythm of Chicago, where world-famous architecture, rich history, and incredible dining come together for an unforgettable journey.

Soak in the skyline as you cruise along the Chicago River, admiring the architectural wonders that define the city.
Feel the energy of the bustling streets, from historic landmarks to lively entertainment districts.


Choose Your Perfect Travel Date

Dive Into Chicago's  Top Attractions!

Millennium Park

Step into the heart of Chicago at Millennium Park, home to the iconic Cloud Gate—affectionately known as The Bean. Marvel at its seamless, reflective surface, capturing the city skyline in a mesmerizing display.

Navy Pier

Step into the excitement of Navy Pier, Chicago’s premier lakefront destination! Take in breathtaking views of Lake Michigan, explore lively shops, and indulge in delicious local flavors.

 Architecture River Cruise

Step aboard a scenic river cruise and witness Chicago’s iconic skyline from the water. Glide along the Chicago River, passing by world-renowned architectural marvels, from the historic Wrigley Building to the towering Willis Tower.

Step into a world of timeless Italian flavors at The Italian Village, a Chicago institution established in 1927. This legendary restaurant has been serving authentic Italian cuisine for nearly a century, capturing the heart and soul of Italy in every dish.

Itinerary Icon

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 (departure times may vary). We’ll head towards the Sarnia Canada/U.S. border, so be sure to have your essential travel documents ready for U.S. entry. Enjoy a refreshing coffee break along the way.

    11:30 AM – Quick stop at duty-free before crossing the border into the U.S.

    1:30 PM – 2:30 PM – Take a 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, located in a Chicago suburb, just minutes from downtown. The rest of the evening is yours to enjoy at your leisure.


  • Day 2 | Discovering Chicago

    NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.


    8:00 AM – Depart hotel for a day of exploration.

    8:45-9:00 AM – Arrive at the iconic United Center for a brief stop.

    9:15-9:30 AM – Depart for the next destination.

    9:45-10:00 AM – Arrive at Millennium Park, Chicago’s top attraction.

    10:30-10:45 AM – Enjoy a 45-minute guided walking tour featuring highlights like the Pritzker Pavilion, Cloud Gate (The Bean), and Crown Fountain. (Clean, free restrooms available.)

    11:30-11:45 AM – Cross the street for a free, escorted 30-minute visit to the Chicago Cultural Center, housed in the city’s original library. (Restrooms available.)

    12:00-12:15 PM – Scenic drive through The Loop, taking in the Riverwalk, Willis Tower (formerly Sears Tower), and more. Continue to North Michigan Avenue, passing by landmarks like the Wrigley Building, Tribune Tower, and Water Tower Place.

    12:20-12:30 PM – Enjoy approximately 4 hours of free time at Water Tower Place, offering upscale shopping and a variety of indoor dining options.

    5:00 PM – Begin the return journey.

    5:45-6:00 PM – Arrive at Oak Brook Center for an independent dinner in the restaurant area. (Bus will return at the agreed time to pick up the group.)


  • DAY 3 | Uncover Chicago’s Iconic Landmarks & Hidden Gems

    NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.


    8:00 AM – Depart the hotel for Buckingham Fountain.

    8:45 AM – Brief stop to disembark and take photos of the stunning 1927 fountain, a majestic gateway to Lake Michigan.

    9:15 AM – After a scenic drive along Chicago’s sandy beaches, arrive at the iconic Wrigley Field. Explore the surrounding area of this 110-year-old stadium during your one-hour independent time.

    10:15 AM – Depart Wrigley Field for a drive through the Gold Coast and Inner Lake Shore Drive.

    Stop for a view and photo op at the famous Mies van der Rohe-designed apartments (1948-56), a landmark of modern architecture.

    11:30 AM – Arrive at the Michigan Avenue Bridge for an exceptional architecture river cruise (cost not included)

    1:45 PM –  Head directly to Navy Pier.

     Arrive at historic Navy Pier (1916), originally a shipping terminal and later transformed into a lively hub of restaurants, sculptures, attractions, and breathtaking lake views.

    2:00 PM – 4:00 PM – Enjoy free time to explore Navy Pier at your own pace.

    4:00 PM – Reboard the bus and head to Museum Campus. Disembark at Planetarium Point for a group photo with the city’s best view, blending lake and skyline.

    4:15 PM – Arrive on State Street for a walking tour, including former Marshall Field’s (now Macy’s) and the historic Carson Pirie Scott building (designed by Louis Sullivan). Learn about the area’s rich architectural history.

    5:30 PM – Dinner drop-off at the legendary Italian Village (est. 1927), Chicago’s oldest and best Italian restaurant, still owned by the founding family. Enjoy special seating and a free wine discussion by the wine director, featuring the city’s most extensive wine collection. 

    As a bonus, take in the newly unveiled Tuscany-inspired mural by renowned local artist Nancy Wright Gelband, with the possibility of a personal appearance by the artist to discuss her work.

    8:00 PM – 8:15 PM – Depart for the hotel.

    9:00 PM – Approximate arrival back at the hotel.



  • DAY 4 | Depart for home » Toronto

    NOTE: The itinerary is subject to change due to weather, traffic, local events, attraction availability, and other unforeseen circumstances.


    6:30 AM - 7:30 AM

    Enjoy a delicious breakfast at the hotel (included) before checking out.

    7:30 AM

    Depart from the hotel and begin your journey back to Toronto.

    10:00 AM

    Take a refreshing coffee break on the way.

    2:00 PM - 4:00 PM

    Stop at the Prime Outlet Mall in Birch Run, Michigan. Shop, enjoy lunch, and explore!

    4:00 PM

    Continue your journey and cross the border.

    6:00 PM

    Another coffee break to keep you energized.

    7:30 PM - 9:30 PM

    Anticipate your return to Toronto. We'll drop you off at the same location where you were picked up.

Meeting Points

Your journey, your way!

 We'll confirm the most convenient pick-up location for you two weeks before departure — tailored to suit your needs.

Unwind in style and wake up refreshed—your urban escape awaits!

After exploring the bustling city, retreat to our luxurious hotel, conveniently located near downtown Chicago. Enjoy three nights of comfort, complete with modern amenities and three delightful hotel breakfasts to kick-start your day.

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