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Ultimate 17-Day Route 66 Road Trip Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and River Cruise

Morning

Start your Route 66 adventure with a classic Chicago breakfast at Miller's Pub, a historic establishment. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture.

Afternoon

Board the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the famous buildings and bridges. For lunch, enjoy the vibrant atmosphere and diverse cuisine options at State and Lake Chicago Tavern.

Evening

Experience the dazzling city views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a skip-the-line ticket. Cap off the evening with a delightful dinner at Cindy's Rooftop, offering both great food and a stunning panorama.

Bedtime

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4.72
Chicago Riverwalk
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4.77
Chicago River 1.5-Hour Guided Architecture Cruise
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Art, Museums, and Gourmet Dining

Morning

Begin with a hearty breakfast at Staytion Market & Bar. Then, immerse yourself in art at the world-renowned Art Institute of Chicago with a fast-pass ticket, allowing you to explore the extensive collection at your own pace.

Afternoon

Enjoy a gourmet lunch on a Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, where you can savor the flavors of the city while cruising along the Chicago River. Afterward, take a leisurely walk through the lush greenery of Millennium Park and visit the famous "Bean" sculpture.

Evening

Dine at The Gage, known for its upscale twist on traditional pub fare. Then, indulge in the vibrant nightlife of the city, perhaps catching a live performance at a local venue or exploring the bars and lounges of the River North neighborhood.

Bedtime

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4.61
Art Institute of Chicago
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4.60
Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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Chicago's Culinary Delights and Evening Entertainment

Morning

Start your day with a breakfast at The Franklin Room, offering a cozy and elegant atmosphere. Then, take a guided Chicago Favorite Foods Guided Walking Tour to sample a variety of the city's iconic dishes and learn about its culinary history.

Afternoon

After the tour, explore the vibrant shopping and dining district of The Magnificent Mile. For lunch, stop at Gilt Bar, a stylish spot known for its creative menu and craft cocktails.

Evening

Enjoy a sophisticated dinner at Travelle at The Langham, Chicago, followed by an evening of entertainment. You might catch a show at the historic Chicago Theatre or opt for a more laid-back experience at a local jazz club.

Bedtime

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4.82
Chicago Favorite Foods Guided Walking Tour
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4.65
The Magnificent Mile
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Chicago's Sports and Skyline

Morning

Grab a quick breakfast at Sweetwater Tavern & Grille (Michigan Plaza - Chicago) before heading to the iconic Wrigley Field for a guided tour of this historic baseball stadium.

Afternoon

For lunch, enjoy the casual atmosphere and delicious pub food at Emerald Loop Bar & Grill. Afterward, take a self-guided walk through the charming neighborhood of Lakeview, exploring its shops, cafes, and the scenic Lake Michigan shoreline.

Evening

Dine at Hoyt's Chicago, a local favorite known for its welcoming ambiance and diverse menu. End the day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower), where you can step out onto The Ledge and admire the city lights from 1,353 feet above the ground.

Bedtime

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4.86
Wrigley Field
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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago's Parks and Zoos

Morning

Enjoy a leisurely breakfast at Five Star Bar before heading to Lincoln Park & Zoo, one of the oldest zoos in the country. Spend the morning exploring the zoo and the surrounding Lincoln Park, which also features gardens, a conservatory, and the peaceful North Avenue Beach.

Afternoon

For lunch, try the delicious sandwiches at House of Blues Restaurant & Bar. Afterward, continue your park exploration with a visit to Grant Park, known as Chicago's "front yard," and home to iconic landmarks like Buckingham Fountain and Maggie Daley Park.

Evening

Dine at Bar Louie - Printers Row and then take a relaxing evening stroll along the Chicago Lakefront Trail, enjoying the beautiful views of the city skyline and Lake Michigan.

Bedtime

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4.29
Lincoln Park & Zoo
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4.70
Grant Park
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Chicago's History and Haunts

Morning

Start with breakfast at Exchequer Restaurant & Pub, a historic spot in the heart of the city. Then, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the darker side of Chicago's history, visiting famous crime scenes and haunted locations.

Afternoon

After the tour, have lunch at The Green Door Tavern, one of Chicago's oldest taverns. Then, continue your historical journey with a visit to the Tribune Tower, where you can see fragments of famous buildings from around the world embedded in the exterior walls.

Evening

Dine at Bar Siena, known for its warm and inviting atmosphere. For a unique evening experience, visit the Chicago Medieval Torture Museum and engage in some ghost hunting activities to end the day with a thrill.

Bedtime

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4.68
Chicago Gangsters and Ghosts Guided Walking Tour
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4.61
Tribune Tower
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Chicago's Science and Sweets

Morning

Enjoy a breakfast at The Franklin Room before starting your day at the Museum of Science and Industry, where you can explore interactive exhibits and learn about a wide range of scientific topics.

Afternoon

For lunch, head to 676 Restaurant & Bar, located in the heart of the city. Afterward, satisfy your sweet tooth with a visit to the Chicago Museum of Ice Cream, where you can indulge in a world of ice cream-themed fun and treats.

Evening

Dine at Lockwood Restaurant & Bar, known for its elegant setting and innovative cuisine. Then, take a leisurely evening walk along the Chicago River, enjoying the city lights and the lively atmosphere of the riverfront.

Bedtime

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4.31
Museum of Science and Industry
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4.09
Chicago Museum of Ice Cream
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Chicago's Music and Culinary Scene

Morning

Start your day with a breakfast at State and Lake Chicago Tavern. Then, explore the vibrant neighborhood of Wicker Park, known for its eclectic mix of shops, restaurants, and street art.

Afternoon

For lunch, head to Gilt Bar, a stylish spot with a creative menu. Afterward, immerse yourself in the local music scene with a visit to a live music venue in Wrigleyville or Lincoln Park.

Evening

Dine at The Gage, located near Millennium Park. After dinner, enjoy a performance at the Chicago Symphony Center or explore the nearby The Loop with its theaters and nightlife.

Bedtime

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Wrigleyville
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4.69
Millennium Park
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Chicago's Neighborhoods and Local Eats

Morning

Start with breakfast at Staytion Market & Bar. Then, take a food tour of one of Chicago's diverse neighborhoods, such as Chinatown, Little Italy, or Andersonville, sampling local favorites and learning about the area's history.

Afternoon

After the tour, explore the neighborhood on your own, visiting unique shops, galleries, and landmarks. For lunch, try one of the recommended spots from the tour or opt for a casual meal at a local cafe or deli.

Evening

Dine at Travelle at The Langham, Chicago, known for its upscale dining experience. Afterward, take a leisurely evening walk through the neighborhood, soaking in the local atmosphere and perhaps stopping for a drink at a neighborhood bar or lounge.

Bedtime

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Little Italy
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4.80
Andersonville
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Chicago's Hidden Gems and Local Flavors

Morning

Enjoy a breakfast at Sweetwater Tavern & Grille (Michigan Plaza - Chicago) before heading to one of Chicago's hidden gems, such as the Garfield Park Conservatory, Alfred Caldwell Lily Pool, or Promontory Point, where you can enjoy the natural beauty and tranquility of these lesser-known spots.

Afternoon

For lunch, try a local favorite like Hoyt's Chicago or Five Star Bar. Afterward, explore the unique shops and boutiques of a neighborhood like Logan Square, Bucktown, or Hyde Park, where you can find everything from vintage clothing to handmade crafts.

Evening

Dine at House of Blues Restaurant & Bar, located in the vibrant River North neighborhood. After dinner, catch a live performance at the House of Blues Chicago or explore the nearby galleries and nightlife.

Bedtime

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Logan Square
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Hyde Park
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Chicago's Cultural Heritage and Ethnic Cuisine

Morning

Start with a breakfast at The Franklin Room. Then, visit one of Chicago's cultural institutions, such as the DuSable Museum of African American History, the National Museum of Mexican Art, or the Swedish American Museum, where you can learn about the history and contributions of different ethnic groups to the city.

Afternoon

For lunch, explore the culinary offerings of a neighborhood like Pilsen, Little Village, or Devon Avenue, known for their diverse and authentic restaurants and markets.

Evening

Dine at Bar Siena, offering a warm and inviting atmosphere. Afterward, enjoy a performance at a local theater or music venue, or simply take a leisurely evening stroll through the neighborhood, soaking in the sights and sounds.

Bedtime

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4.50
National Museum of Mexican Art
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4.89
Swedish American Museum
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Chicago's Parks and Picnics

Morning

Start your day with a breakfast at Exchequer Restaurant & Pub. Then, gather some picnic supplies and head to one of Chicago's beautiful parks, such as Washington Park, Jackson Park, or Northerly Island, where you can enjoy a leisurely morning surrounded by nature.

Afternoon

After your picnic, take a walk or bike ride along the Chicago Lakefront Trail, with its stunning views of the city skyline and Lake Michigan. For a late lunch or early dinner, stop at a nearby beachside cafe or restaurant, or head back to the city to try a new spot.

Evening

Dine at The Green Door Tavern, one of Chicago's oldest taverns with a cozy and historic atmosphere. Afterward, enjoy a relaxed evening exploring the shops, galleries, and nightlife of a neighborhood like Roscoe Village, Ukrainian Village, or Wrigleyville.

Bedtime

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5.00
Washington Park
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Northerly Island
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Chicago's Literary Legacy and Bookstore Tour

Morning

Start with a breakfast at Bar Louie - Printers Row. Then, visit the American Writers Museum to learn about the literary history of the United States and its impact on the cultural landscape. Explore interactive exhibits and discover the works of famous American writers.

Afternoon

For lunch, enjoy the casual atmosphere and delicious food at Five Star Bar. Afterward, take a self-guided tour of Chicago's independent bookstores, including 57th Street Books, Myopic Books, Quimby's Bookstore, and more. Browse the shelves and find hidden literary gems.

Evening

Bedtime

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Myopic Books
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3.25
Quimby's Bookstore
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Chicago's Architecture and Culinary Tour

Morning

Enjoy a breakfast at The Franklin Room. Then, embark on a guided Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings and their history. Take in the stunning skyline views from the water.

Afternoon

For lunch, indulge in the gourmet offerings of Travelle at The Langham, Chicago, known for its upscale dining experience. Afterward, take a guided Chicago Favorite Foods Guided Walking Tour to sample a variety of the city's culinary delights and learn about its food culture.

Evening

Dine at Cindy's Rooftop, offering both great food and a stunning panorama. After dinner, enjoy the vibrant nightlife of the city, perhaps catching a live performance at a local venue or exploring the bars and lounges of the River North neighborhood.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.77
Chicago River 1.5-Hour Guided Architecture Cruise
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4.82
Chicago Favorite Foods Guided Walking Tour
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Chicago's Music and Nightlife Scene

Morning

Start with a breakfast at State and Lake Chicago Tavern. Then, explore the vibrant neighborhood of Wicker Park, known for its eclectic mix of shops, restaurants, and street art.

Afternoon

For lunch, head to Gilt Bar, a stylish spot with a creative menu. Afterward, immerse yourself in the local music scene with a visit to a live music venue in Wrigleyville or Lincoln Park.

Evening

Dine at The Gage, located near Millennium Park. After dinner, enjoy a performance at the Chicago Symphony Center or explore the nearby The Loop with its theaters and nightlife.

Bedtime

Find amazing hotels in Chicago, Illinois.