Ultimate Baseball Road Trip from Toronto to Chicago Itinerary

Begin your day with a visit to the Royal Ontario Museum (ROM), home to a diverse collection of art, culture, and nature.

Enjoy a unique dining experience at Pai Northern Thai Kitchen, known for its traditional Thai dishes. After lunch, explore the eclectic Kensington Market.

For dinner, savor the flavors of Spain at Pizzeria Libretto - Danforth. Afterward, take a leisurely stroll at Sugar Beach.

Embark on a guided day trip to Niagara Falls with the option of a boat cruise. Experience the majestic falls up close and take in the breathtaking views.

Enjoy a leisurely lunch at Terroni, known for its authentic Italian cuisine. Afterward, explore the charming town of Niagara-on-the-Lake.

Conclude your day with a delightful dinner at The Black Hoof, a popular spot for charcuterie and unique dishes.

Cross the border into the United States and head to Detroit, Michigan. Visit the Detroit Institute of Arts to explore one of the most significant art collections in the country.

For lunch, enjoy the famous Detroit-style pizza at Buddy's Pizza. Afterward, visit the Detroit Historical Museum to learn about the city's rich history.

Attend a Detroit Tigers baseball game at Comerica Park, immersing yourself in the passion of American baseball. Stay overnight in Detroit.

Travel to Cleveland, Ohio, and start your day with a visit to the Rock and Roll Hall of Fame, a mecca for music lovers.

Enjoy a classic Cleveland meal at Slyman's Restaurant, famous for its corned beef sandwiches. After lunch, take a walk along the Cleveland Lakefront Nature Preserve.

Watch a Cleveland Guardians baseball game at Progressive Field, known for its electric atmosphere. Spend the night in Cleveland.

Arrive in Chicago, the final stop on your baseball road trip. Start with a visit to the Field Museum to explore natural history and anthropology.

Enjoy a Chicago-style hot dog for lunch at Portillo's. Afterward, take a stroll in Millennium Park and see the famous Cloud Gate.

Immerse yourself in the baseball culture of Chicago with a game at Wrigley Field or Guaranteed Rate Field, depending on the schedule. Celebrate the end of your trip with a deep-dish pizza dinner at Lou Malnati's.

Take an architectural boat tour to admire the stunning skyline of Chicago and learn about the city's famous buildings.

For your final meal, indulge in a steak at Gibsons Bar & Steakhouse, a Chicago institution. Spend your last afternoon shopping on the Magnificent Mile.

Depending on your departure time, you may have the opportunity to catch a Chicago White Sox game at Guaranteed Rate Field or simply enjoy a leisurely evening in the city.