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7 Days Portland to Chicago Road Trip Itinerary
Last updated: 2024 Jun 14Exploring Portland's Natural Beauty
Morning
Start your day with a delicious breakfast at Pine State Biscuits. Then, embark on a half-day Columbia River Gorge Waterfalls Tour From Portland Half Day Columbia River Gorge Waterfalls Tour to witness stunning waterfalls and scenic views.
Afternoon
For lunch, savor the flavors of Portland at Nong's Khao Man Gai. In the afternoon, take a guided walking tour of Downtown Portland Guided Walking Tour of Downtown Portland, Oregon to explore the city's vibrant culture and history.
Portland City Exploration
Morning
Enjoy a tasty breakfast at Blue Star Donuts. Then, discover the city on a Portland Half Day City Sightseeing Tour Portland Half Day City Sightseeing Tour to visit iconic landmarks and hidden gems.
Afternoon
For lunch, head to Tasty n Alder for a satisfying meal. In the afternoon, take a Portland Guided Foodie Bike Tour Portland Guided Foodie Bike Tour to experience the culinary delights of the city.
Nature and Adventure in Portland
Morning
Start your day with a delicious breakfast at Aviary. Then, embark on a full-day Gorge Waterfalls & Mt. Hood Tour From Portland Full Day Gorge Waterfalls & Mt. Hood Tour to explore the natural beauty of the region.
Afternoon
Enjoy a delightful lunch at Grassa. In the afternoon, experience the thrill of iFLY Portland First Time Flyer Experience iFLY Portland First Time Flyer Experience for a unique adventure.
Traveling to Chicago
Morning
Start your day with a delicious breakfast at a local cafe in Portland. Then, travel to Chicago for the next part of your adventure.
Afternoon
Upon arrival in Chicago, have lunch at Shake Shack. Explore the city with a Chicago Art Institute Skip-the-Line Tour with Guide Chicago Art Institute Skip-the-Line Tour with Guide in the afternoon.
Chicago City Exploration
Morning
Start your day with a delicious breakfast at Yolk. Explore the city with a Chicago Loop Bike Tour Chicago Loop Bike Adventures Custom Neighborhood Bike Rides in the morning.
Afternoon
For lunch, indulge in a meal at The Capital Grille. In the afternoon, take a Chicago Riverboat Tour to admire the city's architecture Chicago River 1.5-Hour Guided Architecture Riverboat Tour
Evening
Dine at the famous Gibsons Bar & Steakhouse for a classic Chicago dining experience. Wrap up your day with a visit to a local bar or lounge.
Bedtime
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Cultural Delights of Chicago
Morning
Enjoy a delicious breakfast at Eataly. Explore the city's cultural attractions with a visit to the Art Institute of Chicago Chicago Art Institute of Chicago Fast-Pass Ticket in the morning.
Afternoon
For lunch, savor the flavors of Chicago at Carnivale. In the afternoon, take a Chicago Prohibition Speakeasies Bus Tour Chicago Prohibition Speakeasies Bus Tour or Walking Tour for a unique experience.
Final Day in Chicago
Morning
Start your day with a delicious breakfast at Beatnik. Explore more of Chicago with a visit to iconic landmarks like Wrigley Field Wrigley Field in the morning.
Afternoon
For lunch, enjoy a meal at Joe's Seafood, Prime Steak & Stone Crab. In the afternoon, take a Chicago Lakefront Neighborhoods Bike Tour Chicago Lakefront Neighborhoods Bike Tour to discover the city's diverse neighborhoods.
Evening
End your road trip with a memorable dinner at Girl & the Goat. Reflect on your journey over drinks at a local bar or lounge.
Bedtime
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