5-Day Road Trip from Chicago to Michigan Itinerary

Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Take in breathtaking views from one of the tallest buildings in the Western Hemisphere. Next, explore Chicago Loop, where you'll find architectural marvels like the historic Rookery Building.

In the afternoon, embark on another wishlist tour: Chicago: Lakefront and Museum Campus Segway Tour. This tour will take you along Chicago's beautiful lakefront and through its famous Museum Campus. Afterward, visit Adler Planetarium for some celestial exploration.

Dine at Alinea, one of Chicago's most acclaimed restaurants offering an unforgettable culinary experience. Post-dinner, catch a show at the historic Chicago Theatre, known for its grand architecture and world-class performances.

Kick off your last day in Chicago with a visit to Field Museum, home to Sue—the largest T-Rex skeleton ever discovered—and other fascinating exhibits. Then head over to nearby Shedd Aquarium for an underwater adventure.

Take part in another wishlist tour: Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This riverboat tour offers an informative and scenic journey through Chicago's architectural history. Following this tour, explore more marine life at Shedd Aquarium if time permits.

Enjoy dinner at Pizzeria Uno, famous for its deep-dish pizza that originated right here in Chicago. Afterward, visit Navy Pier for some evening fun—ride the Centennial Wheel or simply enjoy lakeside views before preparing for your road trip to Michigan.

Start your day with a visit to the Detroit Institute of Arts, home to an extensive collection of art from around the world. This museum is renowned for its Diego Rivera murals and diverse exhibits. Afterward, take a stroll through the historic Historic Third Ward, where you can admire the architecture and perhaps do some shopping.

In the afternoon, participate in a wishlist tour: Kalamazoo, MI: Murder Mystery Detective Experience. This interactive experience will have you solving a thrilling mystery while exploring Kalamazoo. Afterward, visit the Kalamazoo Nature Center to enjoy some outdoor activities and learn about local wildlife.

For dinner, head to Selden Standard, a highly-rated restaurant known for its farm-to-table cuisine. After dinner, explore downtown Detroit and perhaps catch a live performance at one of the city's many theaters or music venues.

Grand Teton National Park awaits you this morning. Take in the stunning mountain views and perhaps go for a hike on one of the park's many trails. The park is known for its breathtaking scenery and abundant wildlife.

Jenny Lake Trail is your next stop. This trail offers beautiful views of Jenny Lake and the surrounding mountains. It's a great place for hiking, picnicking, or simply relaxing by the water.

The Cook's House is your dining destination this evening. Known for its locally-sourced ingredients and creative dishes, this restaurant offers a memorable dining experience. After dinner, unwind with a visit to Lakefront Brewery, where you can sample some local brews and enjoy live music.