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Route 66 USA Adventure 15 Days Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to Millennium Park, where you can see the iconic Cloud Gate sculpture and enjoy the beautiful gardens. This park is a must-see for any visitor to Chicago.
Afternoon
Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world.
Evening
For dinner, make a reservation at Alinea, one of Chicago's most acclaimed restaurants. Enjoy an unforgettable dining experience with innovative dishes that push culinary boundaries.
Bedtime
Find amazing hotels in Chicago, Illinois.
Exploring Chicago's Rich History
Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Take in breathtaking views of the city from one of the tallest buildings in the world.
Afternoon
Afterward, explore Chicago Loop, where you can admire historic architecture and visit landmarks like The Rookery Building and the Chicago Board of Trade Building.
Evening
Dine at Girl & the Goat, a popular restaurant known for its creative small plates and vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois.
Cultural Gems and Local Flavors
Morning
Start your morning at Field Museum, home to fascinating exhibits on natural history and culture. Don't miss Sue, the largest T. rex skeleton ever discovered.
Afternoon
Take a leisurely stroll along Chicago Riverwalk, where you can enjoy scenic views of the river and city skyline. Stop by one of the many cafes for a coffee break.
Evening
For dinner, head to Joe's Seafood, Prime Steak & Stone Crab for some delicious seafood and steak options.
Bedtime
Find amazing hotels in Chicago, Illinois.
Entertainment and Relaxation
Morning
Visit Shedd Aquarium in the morning to see an impressive array of marine life from around the world. It's perfect for families or anyone interested in aquatic creatures.
Afternoon
Spend your afternoon at Navy Pier, which offers various attractions including shops, restaurants, and entertainment options. Take a ride on the Ferris wheel for great views!
Evening
End your day with dinner at Lou Malnati's Pizzeria, famous for its deep-dish pizza—a true Chicago classic.
Bedtime
Find amazing hotels in Chicago, Illinois.
Architectural Wonders and Local Eats
Morning
Start your day with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city and Lake Michigan from this iconic skyscraper.
Afternoon
Explore Chicago Cultural Center, known for its stunning architecture and free art exhibits. Take your time to appreciate the beautiful Tiffany dome.
Evening
Dine at Portillo's Hot Dogs, a beloved Chicago institution known for its delicious hot dogs, Italian beef sandwiches, and chocolate cake.
Bedtime
Find amazing hotels in Chicago, Illinois.
Historic Landmarks and Vibrant Neighborhoods
Morning
Museum of Science and Industry is a must-visit. Spend your morning exploring interactive exhibits on science, technology, and industry.
Afternoon
Lincoln Park & Zoo offers a relaxing afternoon with beautiful gardens and a variety of animals. It's one of the oldest zoos in the country and free to enter.
Evening
Gibsons Bar & Steakhouse is perfect for dinner. Enjoy classic American steakhouse fare in an upscale setting.
Bedtime
Find amazing hotels in Chicago, Illinois.
Music, Sports, and Scenic Views
Morning
House of Blues is a great spot to start your day with some live music or even just to explore the venue's unique decor.
Afternoon
Wrigley Field is next on the list. Take a tour of this historic baseball stadium or catch a game if you're lucky!
Evening
The Purple Pig offers Mediterranean-inspired dishes in a lively atmosphere—perfect for ending your day.
Bedtime
Find amazing hotels in Chicago, Illinois.
Artistic Exploration and Culinary Delights
Morning
Visit Adler Planetarium in the morning to explore fascinating exhibits about space and astronomy. The planetarium also offers stunning views of the city skyline.
Afternoon
Head over to Chicago Theatre for an afternoon tour of this historic venue. Learn about its rich history and architectural beauty.
Evening
For dinner, make your way to Au Cheval, renowned for its burgers that are often considered some of the best in America.
Bedtime
Find amazing hotels in Chicago, Illinois.
Exploring the Waterfront
Morning
Begin your day with a visit to Navy Pier. This iconic Chicago landmark offers various attractions including shops, restaurants, and entertainment options. Take a ride on the Ferris wheel for great views!
Afternoon
Afterward, take a leisurely stroll along Chicago Riverwalk, where you can enjoy scenic views of the river and city skyline. Stop by one of the many cafes for a coffee break.
Evening
For dinner, head to Joe's Seafood, Prime Steak & Stone Crab for some delicious seafood and steak options.
Bedtime
Find amazing hotels in Chicago, Illinois.
Historic Architecture and Local Flavors
Morning
Start your morning at Rookery Building, an architectural masterpiece designed by Frank Lloyd Wright. Take a guided tour to learn about its history and design.
Afternoon
Explore Chicago Loop, where you can admire historic architecture and visit landmarks like The Rookery Building and the Chicago Board of Trade Building.
Evening
Dine at Girl & the Goat, a popular restaurant known for its creative small plates and vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois.
Cultural Gems and Scenic Views
Morning
Begin your day with a visit to Field Museum, home to fascinating exhibits on natural history and culture. Don't miss Sue, the largest T. rex skeleton ever discovered.
Afternoon
Take in breathtaking views from 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city and Lake Michigan from this iconic skyscraper.
Evening
For dinner, make your way to Au Cheval, renowned for its burgers that are often considered some of the best in America.
Bedtime
Find amazing hotels in Chicago, Illinois.
Artistic Exploration and Culinary Delights
Morning
Visit Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world.
Afternoon
Head over to Chicago Theatre for an afternoon tour of this historic venue. Learn about its rich history and architectural beauty.
Evening
End your day with dinner at Lou Malnati's Pizzeria, famous for its deep-dish pizza—a true Chicago classic.
Bedtime
Find amazing hotels in Chicago, Illinois.
Science and Industry Marvels
Morning
Start your day with a visit to Museum of Science and Industry. This museum offers interactive exhibits on science, technology, and industry. It's a great place to spend a few hours exploring and learning.
Afternoon
Afterward, head over to Lincoln Park & Zoo. This beautiful park offers gardens and a variety of animals. It's one of the oldest zoos in the country and free to enter.
Evening
For dinner, make your way to Smoque BBQ, known for its delicious barbecue dishes. Enjoy some mouth-watering ribs or brisket.
Bedtime
Find amazing hotels in Chicago, Illinois.
Historic Landmarks and Local Eats
Morning
Wrigley Field is a must-visit. Take a tour of this historic baseball stadium or catch a game if you're lucky!
Afternoon
Chicago Cultural Center is next on the list. Known for its stunning architecture and free art exhibits, it's a great place to spend your afternoon.
Evening
Frontera Grill is perfect for dinner. Enjoy delicious Mexican cuisine in an upscale setting.
Bedtime
Find amazing hotels in Chicago, Illinois.
Final Day in Chicago
Morning
Adler Planetarium is a great spot to start your day. Explore fascinating exhibits about space and astronomy while enjoying stunning views of the city skyline.
Afternoon
Chicago Riverwalk offers scenic views of the river and city skyline. Take a leisurely stroll along the riverwalk and stop by one of the many cafes for a coffee break.
Evening
The Purple Pig offers Mediterranean-inspired dishes in a lively atmosphere—perfect for ending your trip on a high note.
Bedtime
Find amazing hotels in Chicago, Illinois.
Adjacent Cities
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