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Roam Around

14 Days Road Trip from Chicago to Niagara Falls

14 Days Road Trip from Chicago to Niagara Falls Itinerary

Last updated: 2024 Jun 14

Exploring Chicago's Culinary Scene

Morning

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. Then, embark on a food walking tour with bike/kayak rental to explore the city's culinary delights Chicago Full Day Food Walking Tour + FREE Bike/Kayak Rental.

Afternoon

Indulge in a mouth-watering lunch at The Purple Pig. Afterward, visit the iconic Chicago Loop for some sightseeing and shopping.

Evening

Enjoy a delightful dinner at Girl & the Goat known for its innovative dishes. End your evening with a relaxing drink at The Signature Room at the 95th for stunning views of the city.

Bedtime

Find amazing hotels in Chicago.

5.00
Chicago Full Day Food Walking Tour + FREE Bike/Kayak Rental
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4.83
Chicago Loop
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Art and Adventure in Chicago

Morning

Start your day with a skip-the-line tour of the Chicago Art Institute Skip-the-Line Tour with Guide.

Afternoon

Embark on a thrilling adventure with a craft brewery tour by barrel bus Chicago Craft Brewery Tour by Barrel Bus.

Evening

Dine at the famous Alinea for a unique culinary experience in Chicago.

Bedtime

Find amazing hotels in Chicago.

4.96
Chicago Art Institute Skip-the-Line Tour with Guide
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4.95
Chicago Craft Brewery Tour by Barrel Bus
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Exploring Chicago's Landmarks

Morning

Explore the historic Wrigley Field and enjoy a neighborhood bike tour Chicago Lakefront Neighborhoods Bike Tour.

Afternoon

Visit the iconic United Center and learn about its history and significance.

Evening

Savor a delicious dinner at Lou Malnati's Pizzeria known for its deep-dish pizza.

Bedtime

Find amazing hotels in Chicago.

4.86
Wrigley Field
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4.87
Chicago Lakefront Neighborhoods Bike Tour
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Adventure and Entertainment

Morning

Embark on a fun-filled escape room adventure Chicago 1-Hour Escape Room Adventure for an exciting start to the day.

Afternoon

Enjoy a leisurely bike ride along the lakefront with a museum campus segway tour Chicago Lakefront and Museum Campus Segway Tour

Evening

Experience the vibrant nightlife of Chicago with a prohibition speakeasies bus tour or walking tour Chicago Prohibition Speakeasies Bus Tour or Walking Tour. End the day with dinner at Gibsons Bar & Steakhouse.

Bedtime

Find amazing hotels in Chicago.

4.93
Chicago 1-Hour Escape Room Adventure
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4.93
Chicago Lakefront and Museum Campus Segway Tour
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Chicago's Architectural Marvels

Morning

Embark on a guided architecture riverboat tour Chicago Architecture River Cruise Skip-the-Ticket Line to admire the city's stunning architecture.

Afternoon

Explore the secret interiors of Chicago with an architecture walking tour Chicago Secret Interiors Architecture Walking Tour

Evening

Dine at Xoco for a taste of authentic Mexican cuisine.

Bedtime

Find amazing hotels in Chicago.

4.83
Chicago Architecture River Cruise Skip-the-Ticket Line
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4.92
Chicago Secret Interiors Architecture Walking Tour
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Nature and Relaxation

Morning

Enjoy a relaxing morning at the Chicago Pedway exploring the underground city.

Afternoon

Spend the afternoon biking through the city's neighborhoods on a guided bike tour Chicago Lakefront Neighborhoods Bike Tour

Evening

Indulge in a delightful dinner at Pequod's Pizza known for its delicious pan-style pizza.

Bedtime

Find amazing hotels in Chicago.

4.94
Chicago Pedway
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4.87
Chicago Lakefront Neighborhoods Bike Tour
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Cultural Exploration in Chicago

Morning

Discover the treasures of the Golden Age with a walking tour Chicago Treasures of the Golden Age Walking Tour

Afternoon

Visit the iconic Marina City and learn about its architectural significance.

Evening

Enjoy a cultural dining experience at Cafe Ba-Ba-Reeba! known for its Spanish tapas.

Bedtime

Find amazing hotels in Chicago.

4.77
Chicago Treasures of the Golden Age Walking Tour
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4.84
Marina City
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Chicago's Hidden Gems

Morning

Explore the secret food spots of Chicago with a food walking tour Chicago Secret Food Tour

Afternoon

Discover the vibrant street art scene of Chicago with a private art experience Shooting + Spinning Private Art Experience

Evening

Dine at The Publican for a farm-to-table dining experience.

Bedtime

Find amazing hotels in Chicago.

4.83
Chicago Secret Food Tour
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5.00
Shooting + Spinning Private Art Experience
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Chicago's Culinary Delights

Morning

Start your day with a delicious breakfast at Lula Cafe. Then, embark on a food walking tour to explore the city's culinary scene Chicago Classic Food Walking Tour with Bike or Kayak Rental

Afternoon

Indulge in a mouth-watering lunch at Kuma's Corner. Afterward, visit the Chicago Board of Trade Building for some sightseeing.

Evening

Enjoy a delightful dinner at Duck Duck Goat known for its Asian-inspired dishes.

Bedtime

Find amazing hotels in Chicago.

4.82
Chicago Classic Food Walking Tour with Bike or Kayak Rental
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4.87
Chicago Board of Trade Building
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Chicago's Unique Experiences

Morning

Embark on a unique city exploration game with the Pink Panther Chicago The Pink Panther City Exploration Game - App Guided

Afternoon

Experience the vibrant atmosphere of the House of Blues House of Blues

Evening

Dine at Crisp for a taste of Korean fried chicken.

Bedtime

Find amazing hotels in Chicago.

Chicago The Pink Panther City Exploration Game - App Guided
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5.00
House of Blues
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Adventure and Relaxation

Morning

Start your day with a thrilling NHL game at the United Center Chicago Chicago Blackhawks NHL Game Ticket at United Center

Afternoon

Relax and unwind with a Christmas Eve gourmet dinner cruise on Lake Michigan Chicago Christmas Eve Gourmet Dinner Cruise Lake Michigan

Evening

Indulge in a delicious dinner at Frontera Grill known for its Mexican cuisine.

Bedtime

Find amazing hotels in Chicago.

5.00
Chicago Chicago Blackhawks NHL Game Ticket at United Center
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5.00
Chicago Christmas Eve Gourmet Dinner Cruise Lake Michigan
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Chicago's Hidden Treasures

Morning

Discover the hidden gems of Chicago with a walking tour Chicago Downtown Donut Tour with Tastings

Afternoon

Explore the vibrant neighborhood of Chinatown with a taste of Chinatown food walking tour Chicago Taste of Chinatown Food Walking Tour

Evening

Dine at Beatnik for a bohemian dining experience.

Bedtime

Find amazing hotels in Chicago.

4.80
Chicago Downtown Donut Tour with Tastings
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4.79
Chicago Taste of Chinatown Food Walking Tour
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Final Day in Chicago

Morning

Spend your morning exploring the Chicago River on a guided architecture cruise Chicago River 1.5-Hour Guided Architecture Riverboat Tour

Afternoon

Visit the iconic Navy Pier for some leisure time and shopping.

Evening

End your Chicago adventure with a dinner at Sepia known for its contemporary American cuisine.

Bedtime

Find amazing hotels in Chicago.

4.71
Chicago River 1.5-Hour Guided Architecture Riverboat Tour
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Road Trip to Niagara Falls

Morning

Embark on a road trip from Chicago to Niagara Falls enjoying the scenic views along the way.

Afternoon

Arrive in Niagara Falls and check into your accommodation. Enjoy a relaxing afternoon exploring the city.

Evening

Dine at Weinkeller for a taste of local cuisine in Niagara Falls.

Bedtime

Find amazing hotels in Niagara Falls.

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