15 Days of Adventure in the Midwest Itinerary

Begin your day with a hike on the French Canyon Trail. This trail is known for its picturesque canyon and waterfall, making it a must-see in Starved Rock.

After your morning hike, have lunch at Tangled Roots Brewing Company, where you can enjoy locally brewed beers and delicious pub fare. Then, continue your adventure with a visit to the Starved Rock Overlook, offering panoramic views of the Illinois River.

End your day with dinner at The Lone Buffalo, which offers farm-to-table dining in a rustic setting.

Start your day with a hike to LaSalle Canyon. This trail is known for its stunning waterfall and beautiful rock formations. It's a great way to experience the natural beauty of Starved Rock.

After your hike, enjoy lunch at Elements at Water Street, where you can savor delicious dishes with a view of the river. Then, explore the Starved Rock Visitor Center to learn more about the park's history and wildlife.

End your day with dinner at The Red Dog Grill, offering a variety of seafood and American dishes in a relaxed setting.

Kick off your day with some paddleboarding on Lake Michigan. The calm morning waters make for an ideal paddleboarding experience. Afterward, grab breakfast at Country Corner Cafe for some local flavors.

In the afternoon, head to Sleeping Bear Dunes National Lakeshore for some sand dune climbing. This area offers breathtaking views of Lake Michigan and is perfect for an adventurous hike. For lunch, stop by The Fishery to enjoy fresh seafood.

Wrap up your day with dinner at Lakeside Charlie's, where you can enjoy a variety of dishes while overlooking the lake.

Start your day with some beach time at Silver Beach County Park. This park offers beautiful sandy shores and clear waters, perfect for swimming or relaxing. For breakfast, visit Shoreline Cafe for some fresh pastries and coffee.

In the afternoon, rent a kayak or paddleboard to explore the lake further. For lunch, stop by The Galley Grill & Bar to enjoy some lakeside dining with great views.

Conclude your day with dinner at Mackinaw Trail Winery & Brewery, where you can enjoy local wines and craft beers along with a delicious meal.

Sleeping Bear Dunes National Lakeshore awaits you this morning for some exhilarating sand dune climbing. The views from the top are simply breathtaking. For breakfast, visit Country Corner Cafe for some hearty morning fare.

Paddleboarding on Lake Michigan is perfect for an afternoon adventure. The calm waters provide an ideal setting for paddleboarding. For lunch, stop by The Fishery to enjoy fresh seafood.

Lakeside Charlie's is your dinner destination tonight, offering a variety of dishes with a beautiful lakeside view.

Begin your day with a hike along the Dune Ridge Trail. This trail offers panoramic views of Lake Michigan and diverse ecosystems. For breakfast, visit Panini Panini for delicious sandwiches and coffee.

Spend your afternoon kayaking on Lake Michigan from Indiana Dunes National Park. The park offers rentals and guided tours that allow you to explore its scenic shoreline. For lunch, dine at Bartlett's Fish Camp, known for its fresh seafood and waterfront views.

Conclude your day with dinner at Holly's Restaurant and Pub, where you can enjoy hearty pub fare in a cozy setting.

Begin your day with a hike on the Cowles Bog Trail. This trail takes you through diverse habitats including wetlands, forests, and dunes. For breakfast, head to Leeds Public House for some hearty morning fare.

Spend your afternoon climbing the dunes at West Beach. The sweeping views of Lake Michigan from the top are worth the effort. Have lunch at Bridges Waterside Grille, which offers waterfront dining and fresh seafood.

Wrap up your day with dinner at Galveston Steakhouse, known for its mouthwatering steaks and cozy atmosphere.

Dune Ridge Trail offers panoramic views of Lake Michigan and diverse ecosystems. Start your day with this invigorating hike. For breakfast, visit Panini Panini for delicious sandwiches and coffee.

Kayaking on Lake Michigan from Indiana Dunes National Park provides an exciting way to explore the shoreline. Rent a kayak or join a guided tour for an unforgettable experience. For lunch, dine at Bartlett's Fish Camp, known for its fresh seafood and waterfront views.

Holly's Restaurant and Pub is perfect for dinner, offering hearty pub fare in a cozy setting.

Start your Chicago adventure with a visit to Millennium Park. Explore its iconic Cloud Gate sculpture (The Bean) and beautiful gardens. For breakfast, head to Lou Malnati's Pizzeria for their famous deep-dish pizza.

In the afternoon, take an architecture river cruise with the tour:  Chicago Architecture River Cruise Skip-the-Ticket Line. This guided tour provides fascinating insights into Chicago's architectural history while cruising along the river. Enjoy lunch afterward at Portillo's Hot Dogs, known for its classic Chicago-style hot dogs.

End your day by visiting  Wrigley Field for an evening baseball game if there's one scheduled or simply take a tour of this historic ballpark. For dinner, dine at  Girl & The Goat, renowned for its innovative dishes.

Start your day by visiting  Chicago Art Institute of Chicago Fast-Pass Ticket. Explore one of the world's greatest art collections. For breakfast, try  Au Cheval for their famous brunch offerings.

In the afternoon, take a stroll along  Chicago Riverwalk and enjoy its vibrant atmosphere. Stop by  The Purple Pig for lunch to savor Mediterranean-inspired small plates.

End your evening with an exciting show at  Chicago Theatre. Afterward, dine at  Joe's Seafood, Prime Steak & Stone Crab for an unforgettable meal.

Begin your Chicago adventure with a visit to Grant Park. Explore its vast green spaces and iconic Buckingham Fountain. For breakfast, head to Lou Malnati's Pizzeria for their famous deep-dish pizza.

In the afternoon, take an architecture river cruise with the tour: Chicago Architecture River Cruise Skip-the-Ticket Line. This guided tour provides fascinating insights into Chicago's architectural history while cruising along the river. Enjoy lunch afterward at Portillo's Hot Dogs, known for its classic Chicago-style hot dogs.

End your day by visiting Wrigley Fieldfor an evening baseball game if there's one scheduled or simply take a tour of this historic ballpark. For dinner, dine at{ R-Girl & The Goat}, renowned for its innovative dishes.

Start your day with a visit to Chicago Cultural Center. This stunning building offers free art exhibits and beautiful architecture. For breakfast, head to Smoque BBQ for some of the best barbecue in the city.

In the afternoon, explore Chicago Pedway, an underground walkway system that connects many of Chicago's downtown buildings. It's a unique way to see the city from a different perspective. For lunch, stop by Portillo's Hot Dogs for their famous Chicago-style hot dogs.

End your day with a visit to House of Blues for an evening of live music and entertainment. Enjoy dinner at Gibsons Bar & Steakhouse, known for its prime steaks and classic cocktails.

Chicago Lakefront Neighborhoods Bike Tour is a great way to start your day. Explore Chicago's beautiful lakefront neighborhoods on this guided bike tour. For breakfast, visit Au Cheval for their famous brunch offerings.

Chicago River 1.5-Hour Guided Architecture Cruise offers fascinating insights into Chicago's architectural history while cruising along the river. Enjoy lunch afterward at The Purple Pig, known for its Mediterranean-inspired small plates.

Adler Planetarium is perfect for an evening visit. Explore the stars and planets in this iconic planetarium. For dinner, dine at Frontera Grill, renowned for its innovative Mexican cuisine.

Begin your day with a visit to{ A-Grant Park[1207]}. Explore its vast green spaces and iconic Buckingham Fountain.For breakfast, head to{ R-Lou Malnati 's Pizzeria}for their famous deep - dish pizza.

In the afternoon, take an architecture river cruise with the tour:{ A-Chicago Architecture River Cruise Skip-the-Ticket Line[46389]}. This guided tour provides fascinating insights into Chicago 's architectural history while cruising along the river.Enjoy lunch afterward at{ R-Portillo 's Hot Dogs}, known for its classic Chicago - style hot dogs.

End your day by visiting{ A-Wrigley Field[1216]}for an evening baseball game if there 's one scheduled or simply take a tour of this historic ballpark.For dinner, dine at{ R-Girl & The Goat}, renowned for its innovative dishes.