8 Days of Culture and City in Chicago & Toronto Itinerary

Begin your morning with the Chicago Architecture River Cruise Skip-the-Ticket Line. This cruise provides an excellent overview of Chicago's architectural history and stunning skyline. After the cruise, grab breakfast at Au Cheval, famous for its mouth-watering burgers.

Spend your afternoon exploring the historic Chicago Board of Trade Building. This landmark is an architectural gem and offers guided tours that delve into its rich history. For lunch, head over to Portillo's Hot Dogs for a taste of Chicago's famous hot dogs.

In the evening, catch a game or concert at the iconic United Center. Whether you're into sports or music, this venue has something for everyone. Enjoy dinner at Gibsons Bar & Steakhouse, renowned for its prime steaks and elegant setting.

Kick off your day with a visit to the renowned Chicago Art Institute of Chicago Fast-Pass Ticket. This museum houses an impressive collection of art from around the world. Enjoy breakfast at the museum's cafe before diving into the exhibits.

After soaking in some art, take a leisurely walk along the picturesque Chicago Riverwalk. It's a perfect spot for people-watching and enjoying views of the city. For lunch, stop by Lou Malnati's Pizzeria to try some authentic Chicago deep-dish pizza.

Conclude your day with an evening visit to Adler Planetarium, where you can gaze at the stars and learn about our universe. Have dinner at nearby Frontera Grill, which offers delicious Mexican cuisine in a lively atmosphere.

Start your morning with a tour of the historic Rookery Building, one of Chicago's oldest high-rises designed by Frank Lloyd Wright. Grab breakfast afterward at nearby cafe Wildberry Pancakes & Cafe.

Spend your afternoon exploring Grant Park (1207), often referred to as 'Chicago's front yard.' It's home to Buckingham Fountain and offers plenty of green space for relaxation. Have lunch at Smoque BBQ (R-Smoque BBQ) for some mouthwatering barbecue delights.

Wrap up your day by visiting Marina City (26036), known as 'the corn cob towers.' These iconic buildings offer stunning views from their observation decks. Enjoy dinner at The Signature Room on 95th (not on wishlist but highly recommended) located in John Hancock Center offering panoramic views along with exquisite dining experience.

Begin your day with a visit to Toronto Islands. These islands offer beautiful parks, beaches, and stunning views of the Toronto skyline. You can rent a bike or take a leisurely walk around the islands. For breakfast, grab a coffee and pastry at the nearby Miku Toronto, known for its delicious offerings.

In the afternoon, head over to Ripley's Aquarium of Canada. This popular attraction features a wide variety of marine life and interactive exhibits. For lunch, enjoy some fresh seafood at Byblos Toronto, which is just a short distance away.

Conclude your day with an evening visit to the iconic CN Tower. Take in breathtaking views of the city from the observation deck. For dinner, savor some exquisite dishes at Alo, one of Toronto's top-rated restaurants.

Royal Ontario Museum (ROM) is your first stop today. This museum offers an extensive collection of art, culture, and natural history from around the world. Enjoy breakfast at the museum's cafe before exploring its vast exhibits.

Distillery Historic District awaits you in the afternoon. This pedestrian-only village is filled with galleries, boutiques, and cafes housed in historic buildings. For lunch, try some Italian cuisine at Terroni Adelaide, located within walking distance.

Toronto Guided Night Tour with CN Tower Entry will be your evening highlight. This tour provides a unique perspective of Toronto's landmarks illuminated at night. Afterward, dine at Scaramouche Restaurant, known for its elegant ambiance and gourmet dishes.

Art Gallery of Ontario is your morning destination. This gallery boasts an impressive collection of Canadian and international art. Start your day with breakfast at their on-site cafe before diving into the exhibits.

Toronto Chinatown and Kensington Market Guided Tour offers a vibrant cultural experience in the afternoon. Explore these bustling neighborhoods filled with unique shops and eateries. For lunch, enjoy some Asian fusion cuisine at DaiLo nearby.

Entertainment District comes alive in the evening with theaters, restaurants, and nightlife options. Catch a show or simply stroll around this lively area. Have dinner at Richmond Station, known for its farm-to-table dining experience.

Start your final day with a visit to Humber Bay Park (17390). This scenic park offers walking trails along Lake Ontario's shoreline perfect for relaxation & bird watching.Enjoy breakfast picnic style by grabbing some pastries from local bakery Blackbird Baking Co.(not on wishlist but highly recommended)

Spend afternoon exploring Queen's Park (28654), home to Ontario Legislative Building & beautiful gardens ideal spot for leisurely strolls.For lunch head over Pai Northern Thai Kitchen(R-Pai Northern Thai Kitchen) offering authentic Thai flavors.

End trip on high note by taking private helicopter tour two(A-Toronto Private Helicopter Tour Two) providing aerial view cityscape.Dine farewell dinner Jacobs Co.Steakhouse(R-Jacobs Co.Steakhouse) renowned premium steaks elegant setting.