Welcome to a 15-day adventure that takes you through the eclectic streets of Portland, Oregon, and the architectural wonders of Chicago, Illinois. Portland, known as the "City of Roses," offers a unique blend of natural beauty and urban charm, while Chicago, the "Windy City," is a hub of culture and history with its iconic skyline and vibrant neighborhoods. This itinerary is designed to immerse you in the local culture, from the lush landscapes of the Pacific Northwest to the bustling streets of the Midwest.

Portland is a city that thrives on creativity and sustainability, with a rich history dating back to its founding in 1845. Known for its coffee culture, craft breweries, and food carts, Portland is a haven for foodies and nature lovers alike. Meanwhile, Chicago's history is deeply intertwined with its architecture, from the Great Chicago Fire of 1871 to the rise of the skyscraper. The city's diverse neighborhoods offer a tapestry of experiences, from world-class museums to deep-dish pizza.

As you journey from the serene landscapes of Portland to the dynamic energy of Chicago, you'll experience the best of both worlds. Whether you're hiking through the Columbia River Gorge or cruising along the Chicago River, this itinerary promises a blend of relaxation and excitement, with plenty of opportunities to savor local flavors and create lasting memories.

Portland

Days 1-5: Exploring Portland's Natural and Urban Wonders

Begin your journey in Portland, a city that seamlessly blends urban sophistication with natural beauty. Start your mornings with a visit to Stumptown Coffee Roasters, a local favorite known for its expertly brewed coffee. For breakfast, head to Tasty n Alder, where you can indulge in their famous Korean Fried Chicken and Eggs.

Spend your days exploring the city's lush parks and gardens. Don't miss the Multnomah Falls and Columbia River Gorge Half-Day Hiking Tour, where you'll witness breathtaking waterfalls and ancient forests.

For a unique dining experience, embark on a 2.5-hour Dinner Cruise on the Willamette River, where you'll enjoy locally sourced cuisine against the backdrop of Portland's city lights.

For accommodations, consider staying at The Nines, a Luxury Collection Hotel, or the Embassy Suites by Hilton Portland Downtown for a blend of comfort and convenience.

Chicago

Days 6-15: Discovering Chicago's Architectural and Culinary Delights

Fly from Portland to Chicago using Trip.com or Kiwi.com for the best deals.

Chicago is a city that captivates with its stunning architecture and vibrant culture. Start your exploration with a Chicago River 90-Minute Architecture Tour to admire the city's iconic skyline.

For a taste of Chicago's culinary scene, join the Chicago Favorites Ultimate Food and Walking Tour, where you'll sample deep-dish pizza, hot dogs, and more.

For a unique perspective of the city, visit the 360 CHICAGO Observation Deck for panoramic views of the city and Lake Michigan.

Stay at The Peninsula Chicago or Freehand Chicago for a luxurious and comfortable stay.

As your journey comes to an end, you'll leave with a deeper appreciation for the diverse cultures and landscapes of Portland and Chicago. From the serene beauty of the Pacific Northwest to the vibrant energy of the Midwest, this itinerary offers a perfect blend of relaxation and adventure.