Midwest Road Trip: From Montana to Chicago Itinerary

Enjoy a delicious breakfast at Honeypie, known for its farm-to-table comfort food. Then, spend the morning exploring the Harley-Davidson Museum and learning about the history of this iconic American brand.

For lunch, head to The Vanguard, a gastropub with a creative menu. Afterward, take a brewery tour at Lakefront Brewery and sample some of their award-winning beers.

In the evening, have dinner at Goodkind, a restaurant focused on local and seasonal ingredients. Afterward, explore the vibrant nightlife of the Bay View neighborhood.

Start your day with a classic Chicago breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Then, head to the Art Institute of Chicago to explore one of the oldest and largest art museums in the country.

For lunch, indulge in a deep dish pizza at Lou Malnati's Pizzeria, a Chicago institution. Afterward, take a stroll in Millennium Park and see the famous Cloud Gate "Bean".

Enjoy a scenic dinner at The Signature Room at the 95th, with stunning views of the city. Afterward, take a Chicago Riverwalk to see the city lights reflected in the water.

Start your day with a brunch at The Publican, a popular spot for its eclectic menu. Then, take the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's famous architecture.

For a late lunch, try the innovative cuisine at Alinea, a three-Michelin-star restaurant. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.

Dine at Girl & The Goat, a top-rated restaurant known for its bold flavors. After dinner, take a Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city.

Enjoy a leisurely breakfast at Little Goat Diner, a cozy spot with a creative menu. Then, spend the morning exploring the Field Museum and the Shedd Aquarium.

For lunch, savor the flavors of Mexico at Frontera Grill, a renowned restaurant by chef Rick Bayless. Afterward, visit the Adler Planetarium for a journey through the universe.

Conclude your trip with a memorable dinner at Au Cheval, famous for its burger. Afterward, take a Chicago Riverwalk to enjoy the city's nightlife.