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Ultimate 15-Day Route 66 Road Trip Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and River Cruise

Morning

Start your journey with breathtaking views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Then, enjoy a delightful breakfast at Sweetwater Tavern & Grille (Michigan Plaza - Chicago).

Afternoon

Immerse yourself in the city's architecture with a Chicago River 1.5-Hour Guided Architecture Cruise. After the cruise, savor a classic Chicago lunch at Billy Goat Tavern (Millennium Park).

Evening

Conclude your day with a visit to the iconic The Chicago Theatre Tour Experience. For dinner, indulge in the vibrant atmosphere of Bub City with its live music and delicious BBQ.

Bedtime

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4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.77
Chicago River 1.5-Hour Guided Architecture Cruise
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Art and Science in the Windy City

Morning

Explore the masterpieces at the Art Institute of Chicago and then have a cultural breakfast at The Dearborn.

Afternoon

Dive into the wonders of the natural world at the Field Museum. For lunch, enjoy the fresh and sustainable dishes at Doc B's Restaurant (River North).

Evening

Conclude your day with a visit to the Adler Planetarium, where you can explore the universe. For dinner, head to FireLake Grill House and Cocktail Bar for a cozy and elegant dining experience.

Bedtime

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4.61
Art Institute of Chicago
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4.56
Field Museum
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Magnificent Mile and Navy Pier

Morning

Take a stroll down the The Magnificent Mile, Chicago's premier shopping destination. Enjoy breakfast at LUXBAR to fuel up for the day.

Afternoon

Spend your afternoon at the lively Navy Pier, where you can enjoy rides, attractions, and the stunning lakefront. Have lunch with a view at Miller's Pub.

Evening

Dine at Bar Mar by José Andrés, offering a mix of traditional and avant-garde Spanish flavors. After dinner, take a leisurely walk along the Chicago Riverwalk to end the day.

Bedtime

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4.65
The Magnificent Mile
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4.48
Navy Pier
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Chicago's Parks and Skyline

Morning

Start your day with a visit to the beautiful Millennium Park, home to the famous "Bean." Enjoy breakfast at Roanoke Restaurant, known for its local and seasonal menu.

Afternoon

Explore the greenery of Grant Park and then head to the historic Wrigley Building. For lunch, try the innovative dishes at Bar Siena.

Evening

Witness the city lights from the Skydeck Chicago at Willis Tower (Sears Tower), and if you're feeling adventurous, step out onto The Ledge for a thrilling experience. Dinner can be enjoyed at The Gage, offering a rustic yet refined menu.

Bedtime

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4.69
Millennium Park
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4.70
Grant Park
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Chicago's Sports and Culinary Scene

Morning

Pay homage to the sporting history at Wrigley Field, home of the Chicago Cubs. Enjoy a breakfast at Randolph Tavern in the heart of the city's vibrant restaurant district.

Afternoon

Afterward, take a walk through the charming Lincoln Park & Zoo, one of the oldest zoos in the country. For lunch, head to Burger Bar Chicago for a wide selection of gourmet burgers.

Evening

Experience the lively atmosphere of the Wrigleyville neighborhood. Dine at State and Lake Chicago Tavern, known for its modern take on classic American fare.

Bedtime

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4.86
Wrigley Field
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4.29
Lincoln Park & Zoo
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Historic Springfield and Lincoln's Legacy

Morning

Begin your day with a visit to the Abraham Lincoln Presidential Library and Museum, where you can immerse yourself in the life and times of the 16th President. Enjoy a hearty breakfast at Obed & Isaac's Microbrewery and Eatery.

Afternoon

Explore the Illinois State Capitol and take a guided tour to learn about the state's political history. For lunch, savor the flavors of the region at D'Arcy's Pint.

Evening

Conclude your day with a visit to the Lincoln Home National Historic Site, where you can walk in the footsteps of the Lincolns. Enjoy a relaxing dinner at Charlie Parker's Diner, a local favorite.

Bedtime

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Gateway to the West

Morning

Start your day with a visit to the iconic Gateway Arch, the symbol of St. Louis. Enjoy breakfast with a view at Three Sixty.

Afternoon

Explore the interactive exhibits at the City Museum, a unique and creative space. For lunch, head to Bogart's Smokehouse for some of the best BBQ in the city.

Evening

Conclude your day with a leisurely stroll through the Missouri Botanical Garden, one of the oldest botanical institutions in the country. Enjoy a delightful dinner at Blueberry Hill, a St. Louis landmark.

Bedtime

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Historic and Cultural Delights

Morning

Begin with a visit to the St. Louis Union Station, a historic train station that has been transformed into a shopping and entertainment complex. Enjoy breakfast at The Fountain on Locust, known for its Art Deco ambiance.

Afternoon

Explore the exhibits at the St. Louis Art Museum, located in Forest Park. For lunch, head to Pappy's Smokehouse for some of the best ribs in the city.

Evening

Conclude your day with a visit to the Anheuser-Busch Brewery, where you can take a tour and learn about the brewing process. Enjoy a beer-themed dinner at Alpha Brewing Company.

Bedtime

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Family Fun and Educational Excursions

Morning

Spend the morning at the St. Louis Zoo, one of the top zoos in the country. Enjoy breakfast at Sugarfire Smoke House, known for its creative BBQ dishes.

Afternoon

After the zoo, visit the St. Louis Science Center and the Magic House, St. Louis Children's Museum for interactive and educational experiences. For lunch, head to Gringo Jones Imports for a unique dining atmosphere.

Evening

Conclude your day with a relaxing dinner cruise on the Spirit of St. Louis, where you can enjoy the city skyline from the water. Dine on board and enjoy live entertainment.

Bedtime

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Historic and Cultural Springfield

Morning

Begin your day with a visit to the Old State Capitol, where Abraham Lincoln served as a legislator. Enjoy breakfast at Head West Sub Stop.

Afternoon

Explore the Illinois State Museum and learn about the natural and cultural history of the state. For lunch, head to Long Nine Junction for a taste of local cuisine.

Evening

Conclude your day with a visit to the Dana-Thomas House, a stunning example of Frank Lloyd Wright's Prairie style architecture. Enjoy a fine dining experience at Maldaner's Restaurant, a Springfield institution.

Bedtime

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Chicago's Culinary Delights

Morning

Start your day with a visit to the Museum of Science and Industry, where you can explore the interactive exhibits. Enjoy breakfast at The Purple Pig, known for its Mediterranean-inspired menu.

Afternoon

After the museum, take a break and relax at Oak Street Beach. For lunch, head to Giordano's, a Chicago institution famous for its deep-dish pizza.

Evening

Conclude your day with a visit to the Chicago History Museum, where you can learn about the city's past. Enjoy a dinner cruise on the Odyssey Chicago River, where you can dine and enjoy the city skyline from the water.

Bedtime

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4.31
Museum of Science and Industry
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Chicago's Neighborhoods and Nightlife

Morning

Start your day with a visit to Chinatown, where you can explore the vibrant culture and enjoy breakfast at MingHin Cuisine.

Afternoon

After Chinatown, head to Wicker Park and Bucktown for some shopping and to explore the hipster neighborhoods. For lunch, head to Au Cheval, known for its famous burger.

Evening

Conclude your day with a visit to The Second City, where you can enjoy some comedy. For dinner, head to Alinea, one of the best restaurants in the city for a fine dining experience.

Bedtime

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Chicago's Music and Entertainment Scene

Morning

Start your day with a visit to Reggies, a famous music venue in the city. Enjoy breakfast at Portillo's Hot Dogs, a Chicago classic.

Afternoon

After breakfast, head to Millennium Park and Grant Park for some outdoor time. For lunch, head to Rick Bayless' Frontera Grill, known for its Mexican cuisine.

Evening

Conclude your day with a visit to The Green Mill, a historic jazz club. For dinner, head to Gene & Georgetti, one of the oldest steakhouses in the city.

Bedtime

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4.69
Millennium Park
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4.70
Grant Park
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Chicago's Sports and Recreation

Morning

Start your day with a visit to Soldier Field, home of the Chicago Bears. Enjoy breakfast at Portillo's Hot Dogs, a Chicago classic.

Afternoon

After breakfast, head to Lakefront Trail for a bike ride or a walk along the lake. For lunch, head to Rick Bayless' Frontera Grill, known for its Mexican cuisine.

Evening

Conclude your day with a visit to Wrigley Field, home of the Chicago Cubs. For dinner, head to Gene & Georgetti, one of the oldest steakhouses in the city.

Bedtime

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4.76
Soldier Field
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Wrigley Field
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Chicago's Final Farewell

Morning

Start your day with a visit to The Magnificent Mile for some last-minute shopping. Enjoy breakfast at The Signature Room at the 95th, where you can enjoy a meal with a view.

Afternoon

After breakfast, head to Navy Pier for some final fun and entertainment. For lunch, head to The Purple Pig, known for its Mediterranean-inspired menu.

Evening

Conclude your trip with a visit to Skydeck Chicago at Willis Tower (Sears Tower), where you can enjoy the city skyline one last time. For dinner, head to The Signature Room at the 95th, where you can enjoy a meal with a view.

Bedtime

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