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Ultimate 22-Day Route 66 Road Trip Adventure

Ultimate 22-Day Route 66 Road Trip Adventure Itinerary

Last updated: 2024 Jun 14

City Icons and River Cruise

Morning

Start your iconic Route 66 journey with a hearty breakfast at Miller's Pub, a historic Chicago establishment. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture and the famous Wrigley Building.

Afternoon

Enjoy a classic Chicago experience with a Chicago River 1.5-Hour Guided Architecture Cruise. For lunch, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for their signature dishes.

Evening

Conclude your first day with a visit to the The Magnificent Mile, Chicago's premier shopping district. For dinner, indulge in the vibrant atmosphere and cuisine at The Gage.

Bedtime

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4.72
Chicago Riverwalk
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4.39
Wrigley Building
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Museum Marvels and Sky-high Views

Morning

Begin with a visit to the renowned Art Institute of Chicago. After exploring the art, have breakfast at The Dearborn, located nearby.

Afternoon

Spend your afternoon at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), enjoying skip-the-line access with a Chicago 360 Chicago Observation Deck Skip-the-Line Ticket. For lunch, head to Bar Louie - Printers Row for a casual yet satisfying meal.

Evening

Dine with a view at Cité, a restaurant with stunning skyline panoramas. Afterward, take a leisurely walk in Millennium Park and witness the famous "Bean" sculpture, also known as Cloud Gate.

Bedtime

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4.61
Art Institute of Chicago
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4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Family Fun and Navy Pier

Morning

Start with a visit to the family-friendly Navy Pier, where you can enjoy various attractions and the scenic lakefront. Have breakfast at Doc B's Restaurant (River North) before you begin your day of fun.

Afternoon

Explore the underwater world at the Shedd Aquarium, located near the pier. For lunch, head to Bub City for some delicious barbecue.

Evening

Cap off the day with a ride on the Centennial Wheel at Navy Pier, offering stunning views of the city and Lake Michigan. Enjoy dinner at FireLake Grill House and Cocktail Bar for a cozy and relaxing atmosphere.

Bedtime

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4.48
Navy Pier
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4.75
Shedd Aquarium
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Historic Buildings and Evening Delights

Morning

Immerse yourself in history with a visit to the Tribune Tower and the Chicago History Museum. For breakfast, try the delightful pastries at LUXBAR.

Afternoon

Afterward, take a guided tour of the Chicago Theatre to learn about its rich history and stunning architecture. Enjoy a lunch break at Bar Mar by José Andrés, known for its innovative dishes.

Evening

Experience the vibrant nightlife of Chicago at River North, known for its array of bars and entertainment venues. Enjoy a dinner at Bar Siena and then explore the area's offerings.

Bedtime

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4.61
Tribune Tower
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4.77
Chicago History Museum
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Artistic Exploration and Culinary Delights

Morning

Begin your day with a visit to the Museum of Contemporary Art Chicago, where you can explore the latest in contemporary art. Enjoy breakfast at Plymouth Restaurant & Rooftop Bar with a view of the city.

Afternoon

For lunch, head to Burger Bar Chicago for a satisfying burger experience. Afterward, take a guided tour of the Marina City, also known as the "Corn Cob Towers," to learn about its unique architecture and history.

Evening

Conclude your day with a gourmet dinner at Bar Siena, offering a refined Italian dining experience. Afterward, take a leisurely walk along the Chicago River to enjoy the city lights and the evening ambiance.

Bedtime

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4.84
Marina City
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4.61
Chicago River
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Culinary and Cultural Wonders

Morning

Start with a delightful breakfast at The Gage, known for its innovative cuisine. Afterward, take a guided tour of the Chicago Cultural Center, a historic landmark with stunning architecture and cultural exhibits.

Afternoon

For lunch, head to State and Lake Chicago Tavern for a modern take on classic American dishes. Spend your afternoon exploring the Chicago Pedway, an underground network of walkways and shops, providing a unique perspective of the city.

Evening

Enjoy a memorable dinner at The Signature Room at the 95th, located on the 95th floor of the John Hancock Center, offering breathtaking views of the city skyline. Afterward, take a stroll along the Chicago Riverwalk and enjoy the evening breeze.

Bedtime

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4.72
Chicago Riverwalk
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Sports and Scenic Views

Morning

Start your day with a visit to the iconic Wrigley Field, home of the Chicago Cubs. For breakfast, enjoy the lively atmosphere at Sluggers World Class Sports Bar & Grill, located near the stadium.

Afternoon

Afterward, take a leisurely walk in the nearby Lincoln Park, one of the city's most charming neighborhoods. For lunch, head to The J. Parker, a rooftop bar and restaurant with panoramic views of the city skyline and Lake Michigan.

Evening

Enjoy a relaxing dinner cruise on the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, where you can savor delicious food and drinks while taking in the beautiful sights along the Chicago River.

Bedtime

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4.86
Wrigley Field
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4.29
Lincoln Park
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Music, Museums, and More

Morning

Start your day with a visit to the Chicago Blues Museum, where you can learn about the history and impact of blues music in the city. Enjoy breakfast at Hard Rock Cafe Chicago, located in the heart of the vibrant River North neighborhood.

Afternoon

Afterward, explore the Magnificent Mile for some world-class shopping and cultural attractions. For lunch, head to The Purple Pig, known for its eclectic menu and lively atmosphere.

Evening

Spend your evening at the House of Blues Chicago, where you can catch a live music performance in an intimate setting. Enjoy dinner at The Dearborn, offering a modern take on classic American fare.

Bedtime

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4.65
Magnificent Mile
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Hidden Gems and Local Flavors

Morning

Start with a visit to the Chicago Pedway, an underground network of walkways and shops that provides a unique perspective of the city. For breakfast, enjoy the local flavors at BomboBar, known for its creative pastries and coffee.

Afternoon

Explore the vibrant neighborhood of Wicker Park, known for its eclectic mix of shops, restaurants, and street art. For lunch, head to Big Star, a popular spot for tacos and margaritas.

Evening

Conclude your day with a visit to The 606, also known as the Bloomingdale Trail, a unique elevated park and trail system. Enjoy dinner at Au Cheval, famous for its indulgent burgers and a lively atmosphere.

Bedtime

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Chicago's Green Spaces and Culinary Delights

Morning

Start your day with a visit to the Garfield Park Conservatory, one of the largest and most stunning conservatories in the United States. Enjoy breakfast at Dove's Luncheonette, known for its delicious Mexican-inspired dishes.

Afternoon

Afterward, explore the beautiful Humboldt Park, a vibrant neighborhood with a large park that offers a peaceful escape from the city. For lunch, head to Parson's Chicken & Fish, a local favorite for fried chicken and refreshing cocktails.

Evening

Conclude your day with a visit to Logan Square, a hip and trendy neighborhood with a wide range of bars, restaurants, and shops. Enjoy dinner at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection.

Bedtime

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Chicago's South Side and Cultural Heritage

Morning

Start with a visit to the DuSable Museum of African American History, the first museum of its kind in the country. For breakfast, enjoy the soulful flavors at Lem's Bar-B-Q, a local institution known for its ribs and hot links.

Afternoon

Afterward, explore the historic Bronzeville neighborhood, known as the "Black Metropolis" and a center of African American culture and heritage. For lunch, head to Valois Restaurant, a classic diner that has been serving the community for decades.

Evening

Conclude your day with a visit to Hyde Park, home to the prestigious University of Chicago and the Museum of Science and Industry. Enjoy dinner at Peach's Restaurant, a cozy spot known for its Southern-inspired dishes and hospitality.

Bedtime

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Hyde Park
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Chicago's North Side and Neighborhood Charms

Morning

Start with a visit to the Lincoln Park Zoo, one of the oldest and most beloved zoos in the country. For breakfast, enjoy the laid-back vibes and delicious food at Ann Sather, a local favorite for Swedish comfort food.

Afternoon

Afterward, explore the charming Lincoln Park neighborhood, with its tree-lined streets, boutique shops, and the serene Lakefront Trail. For lunch, head to The Wiener's Circle, a Chicago institution known for its hot dogs and lively atmosphere.

Evening

Conclude your day with a visit to Lakeview, a vibrant neighborhood with a diverse mix of bars, restaurants, and entertainment venues. Enjoy dinner at Schubas Tavern, a historic music venue with a cozy restaurant serving elevated pub fare.

Bedtime

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4.29
Lincoln Park Zoo
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4.29
Lincoln Park
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Chicago's West Side and Cultural Hotspots

Morning

Start with a visit to the Garfield Park Conservatory, one of the largest and most stunning conservatories in the United States. Enjoy breakfast at Dove's Luncheonette, known for its delicious Mexican-inspired dishes.

Afternoon

Afterward, explore the beautiful Humboldt Park, a vibrant neighborhood with a large park that offers a peaceful escape from the city. For lunch, head to Parson's Chicken & Fish, a local favorite for fried chicken and refreshing cocktails.

Evening

Conclude your day with a visit to Logan Square, a hip and trendy neighborhood with a wide range of bars, restaurants, and shops. Enjoy dinner at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection.

Bedtime

Find amazing hotels in Chicago.

Chicago's South Side and Cultural Heritage

Morning

Start with a visit to the DuSable Museum of African American History, the first museum of its kind in the country. For breakfast, enjoy the soulful flavors at Lem's Bar-B-Q, a local institution known for its ribs and hot links.

Afternoon

Afterward, explore the historic Bronzeville neighborhood, known as the "Black Metropolis" and a center of African American culture and heritage. For lunch, head to Valois Restaurant, a classic diner that has been serving the community for decades.

Evening

Conclude your day with a visit to Hyde Park, home to the prestigious University of Chicago and the Museum of Science and Industry. Enjoy dinner at Peach's Restaurant, a cozy spot known for its Southern-inspired dishes and hospitality.

Bedtime

Find amazing hotels in Chicago.

Hyde Park
Book Now

Chicago's North Side and Neighborhood Charms

Morning

Start with a visit to the Lincoln Park Zoo, one of the oldest and most beloved zoos in the country. For breakfast, enjoy the laid-back vibes and delicious food at Ann Sather, a local favorite for Swedish comfort food.

Afternoon

Afterward, explore the charming Lincoln Park neighborhood, with its tree-lined streets, boutique shops, and the serene Lakefront Trail. For lunch, head to The Wiener's Circle, a Chicago institution known for its hot dogs and lively atmosphere.

Evening

Conclude your day with a visit to Lakeview, a vibrant neighborhood with a diverse mix of bars, restaurants, and entertainment venues. Enjoy dinner at Schubas Tavern, a historic music venue with a cozy restaurant serving elevated pub fare.

Bedtime

Find amazing hotels in Chicago.

4.29
Lincoln Park Zoo
Book Now

4.29
Lincoln Park
Book Now

Chicago's West Side and Cultural Hotspots

Morning

Start with a visit to the Garfield Park Conservatory, one of the largest and most stunning conservatories in the United States. Enjoy breakfast at Dove's Luncheonette, known for its delicious Mexican-inspired dishes.

Afternoon

Afterward, explore the beautiful Humboldt Park, a vibrant neighborhood with a large park that offers a peaceful escape from the city. For lunch, head to Parson's Chicken & Fish, a local favorite for fried chicken and refreshing cocktails.

Evening

Conclude your day with a visit to Logan Square, a hip and trendy neighborhood with a wide range of bars, restaurants, and shops. Enjoy dinner at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection.

Bedtime

Find amazing hotels in Chicago.

Chicago's South Side and Cultural Heritage

Morning

Start with a visit to the DuSable Museum of African American History, the first museum of its kind in the country. For breakfast, enjoy the soulful flavors at Lem's Bar-B-Q, a local institution known for its ribs and hot links.

Afternoon

Afterward, explore the historic Bronzeville neighborhood, known as the "Black Metropolis" and a center of African American culture and heritage. For lunch, head to Valois Restaurant, a classic diner that has been serving the community for decades.

Evening

Conclude your day with a visit to Hyde Park, home to the prestigious University of Chicago and the Museum of Science and Industry. Enjoy dinner at Peach's Restaurant, a cozy spot known for its Southern-inspired dishes and hospitality.

Bedtime

Find amazing hotels in Chicago.

Hyde Park
Book Now

Chicago's North Side and Neighborhood Charms

Morning

Start with a visit to the Lincoln Park Zoo, one of the oldest and most beloved zoos in the country. For breakfast, enjoy the laid-back vibes and delicious food at Ann Sather, a local favorite for Swedish comfort food.

Afternoon

Afterward, explore the charming Lincoln Park neighborhood, with its tree-lined streets, boutique shops, and the serene Lakefront Trail. For lunch, head to The Wiener's Circle, a Chicago institution known for its hot dogs and lively atmosphere.

Evening

Conclude your day with a visit to Lakeview, a vibrant neighborhood with a diverse mix of bars, restaurants, and entertainment venues. Enjoy dinner at Schubas Tavern, a historic music venue with a cozy restaurant serving elevated pub fare.

Bedtime

Find amazing hotels in Chicago.

4.29
Lincoln Park Zoo
Book Now

4.29
Lincoln Park
Book Now

Chicago's West Side and Cultural Hotspots

Morning

Start with a visit to the Garfield Park Conservatory, one of the largest and most stunning conservatories in the United States. Enjoy breakfast at Dove's Luncheonette, known for its delicious Mexican-inspired dishes.

Afternoon

Afterward, explore the beautiful Humboldt Park, a vibrant neighborhood with a large park that offers a peaceful escape from the city. For lunch, head to Parson's Chicken & Fish, a local favorite for fried chicken and refreshing cocktails.

Evening

Conclude your day with a visit to Logan Square, a hip and trendy neighborhood with a wide range of bars, restaurants, and shops. Enjoy dinner at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection.

Bedtime

Find amazing hotels in Chicago.

Chicago's South Side and Cultural Heritage

Morning

Start with a visit to the DuSable Museum of African American History, the first museum of its kind in the country. For breakfast, enjoy the soulful flavors at Lem's Bar-B-Q, a local institution known for its ribs and hot links.

Afternoon

Afterward, explore the historic Bronzeville neighborhood, known as the "Black Metropolis" and a center of African American culture and heritage. For lunch, head to Valois Restaurant, a classic diner that has been serving the community for decades.

Evening

Conclude your day with a visit to Hyde Park, home to the prestigious University of Chicago and the Museum of Science and Industry. Enjoy dinner at Peach's Restaurant, a cozy spot known for its Southern-inspired dishes and hospitality.

Bedtime

Find amazing hotels in Chicago.

Hyde Park
Book Now

Chicago's North Side and Neighborhood Charms

Morning

Start with a visit to the Lincoln Park Zoo, one of the oldest and most beloved zoos in the country. For breakfast, enjoy the laid-back vibes and delicious food at Ann Sather, a local favorite for Swedish comfort

Afternoon

Evening

4.29
Lincoln Park Zoo
Book Now

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