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![Kentucky and Chicago Adventure](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f3163-5bd8-7e95-b0cc-9411f8a807b6/location121.jpg)
Kentucky and Chicago Adventure Itinerary
Last updated: 2024 Jun 14Southern Charm in Louisville
Morning
Start your Kentucky adventure with a delightful Southern breakfast at Biscuit Belly, known for its mouthwatering biscuits and gravy.
Afternoon
Immerse yourself in the local history with a visit to the Ashland The Henry Clay Estate, the former home of statesman Henry Clay. Afterward, enjoy a traditional Kentucky lunch at Ramsey's Diner.
Evening
In the evening, take a leisurely stroll along the Waterfront Park, a scenic park on the banks of the Ohio River. For dinner, savor the famous Hot Brown at the historic The Brown Hotel.
Bedtime
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Ashland The Henry Clay Estate
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Ashland The Henry Clay Estate
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Bourbon and Beyond in Louisville
Morning
Indulge in a hearty breakfast at Wallace Station Deli and Bakery before embarking on a Bourbon distillery tour. Visit the Evan Williams Bourbon Experience or Angel's Envy Distillery for a taste of Kentucky's finest.
Afternoon
After the distillery tour, have a classic Southern lunch at Hammerheads, known for its unique and delicious dishes. Spend the afternoon exploring the Kentucky Derby Museum at Churchill Downs.
Evening
For dinner, enjoy a farm-to-table experience at Harvest Restaurant, known for its seasonal menu. Afterward, if you're up for some nightlife, head to Meta, a trendy bar with a great cocktail selection.
Bedtime
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4.83Angel's Envy Distillery
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![Visit Reykjavik ATV Reykjavik Peaks Half-Day Tour in Louisville, Kentucky](https://cdn.getyourguide.com/img/tour/62b2e5ace47be.jpeg/21.jpg)
Angel's Envy Distillery
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Horse Country in Lexington
Morning
Travel to Lexington, the heart of Kentucky's Bluegrass region. Start your day with a delicious breakfast at Wild Eggs.
Afternoon
Explore the Kentucky Horse Park, a working horse farm and equine education center. Afterward, have a leisurely lunch at Smithtown Seafood.
Evening
In the evening, take a scenic drive along the Old Frankfort Pike, known for its beautiful horse farms. For dinner, enjoy a fine dining experience at Lockbox.
Bedtime
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4.82Old Frankfort Pike
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Old Frankfort Pike
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Cultural Delights in Cincinnati
Morning
Cross the state border and head to Cincinnati, Ohio. Start your day with a tasty breakfast at Maplewood Kitchen and Bar.
Afternoon
Visit the Cincinnati Zoo and Botanical Garden, known for its diverse animal species and beautiful gardens. Afterward, have a relaxed lunch at Skyline Chili, a local favorite.
Evening
Explore the Cincinnati Art Museum or take a walk along the Smale Riverfront Park. For dinner, enjoy the vibrant food scene at The Eagle OTR.
Bedtime
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Cincinnati Zoo and Botanical Garden
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Cincinnati Zoo and Botanical Garden
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Urban Bourbon Trail in Louisville
Morning
Embark on the Urban Bourbon Trail in Louisville. Start your day with a bourbon-infused breakfast at MilkWood.
Afternoon
Visit some of the iconic stops on the Urban Bourbon Trail, such as Angel's Envy Distillery or Evan Williams Bourbon Experience. Enjoy a Southern lunch at Feast BBQ.
Evening
For dinner, experience the true spirit of Louisville at Jack Fry's, a historic restaurant with a reputation for excellent cuisine. Afterward, enjoy a nightcap at The Silver Dollar, known for its extensive bourbon selection.
Bedtime
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4.83Angel's Envy Distillery
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![Visit Reykjavik ATV Reykjavik Peaks Half-Day Tour in Louisville, Kentucky](https://cdn.getyourguide.com/img/tour/62b2e5ace47be.jpeg/21.jpg)
Angel's Envy Distillery
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Windy City Wonders
Morning
Fly to Chicago, the vibrant metropolis on the shores of Lake Michigan. Start your day with a classic Chicago breakfast at Wildberry Pancakes and Cafe.
Afternoon
Immerse yourself in the city's architecture with a boat tour on the Chicago River. Afterward, have a deep-dish pizza for lunch at Lou Malnati's Pizzeria.
Evening
Explore the iconic Millennium Park and take a selfie at the Cloud Gate. For dinner, enjoy a steak at Gibsons Bar and Steakhouse.
Bedtime
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4.61Chicago River
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Chicago River
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4.69Millennium Park
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Millennium Park
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4.31Cloud Gate
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Cloud Gate
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Art and Culture in Chicago
Morning
Start your day with a visit to the Art Institute of Chicago, home to a world-class collection of art. Have a light breakfast at the museum's Terzo Piano.
Afternoon
Explore the Museum Campus, where you can visit the Field Museum, Shedd Aquarium, and Adler Planetarium. Enjoy a seafood lunch at Shaw's Crab House.
Evening
In the evening, take a walk along the Chicago Riverwalk and enjoy the city lights. For dinner, savor the flavors of Italy at Spiaggia.
Bedtime
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4.61Art Institute of Chicago
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Art Institute of Chicago
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4.56Field Museum
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Field Museum
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![Visit Shedd Aquarium in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
4.75Shedd Aquarium
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![Visit Shedd Aquarium in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
Shedd Aquarium
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![Visit Adler Planetarium in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/59/29.jpg)
4.61Adler Planetarium
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Adler Planetarium
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![Visit Chicago Riverwalk in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
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Chicago Riverwalk
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Farewell to the Windy City
Morning
Spend your last morning in Chicago shopping along The Magnificent Mile. Stop for a coffee at Intelligentsia Coffee.
Afternoon
Visit the 360 Chicago Observation Deck for panoramic views of the city. Have a late lunch at The Signature Room at the 95th.
Evening
Conclude your trip with a sunset visit to the Willis Tower Skydeck. For a memorable farewell dinner, dine at Alinea, a three-Michelin-star restaurant.
Bedtime
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4.65The Magnificent Mile
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The Magnificent Mile
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![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
4.17360 Chicago Observation Deck
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360 Chicago Observation Deck
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![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
4.27Willis Tower Skydeck
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![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
Willis Tower Skydeck
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