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Ultimate 14-Day Illinois Adventure: From Chicago to St. Louis Itinerary
Last updated: 2024 Jun 14Iconic Chicago Beginnings
Morning
Start your adventure with a classic Chicago breakfast at Lou Mitchell's, known for its hearty meals. Afterward, take a self-guided walk along the Chicago Riverwalk to admire the city's architecture.
Afternoon
For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to immerse yourself in world-class art.
Evening
Have a delightful dinner at Giordano's, another renowned spot for Chicago's famous deep-dish pizza. Afterward, take a leisurely walk around Millennium Park and marvel at the "Bean" and the city skyline.
Bedtime
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City Sights and Skyline Views
Morning
Enjoy a delicious breakfast at Xoco, a favorite for Mexican cuisine. Then, take a stroll along the Magnificent Mile for some shopping and iconic city views.
Afternoon
For lunch, savor the flavors of Rick Bayless' Frontera Grill. Afterward, visit the 360 Chicago Observation Deck for panoramic views of the city.
Evening
Dine at the award-winning Alinea for a culinary experience like no other. Conclude your day with a visit to the Chicago Theatre.
Bedtime
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Cultural Immersion in the Windy City
Morning
Start your day with a leisurely breakfast at The Purple Pig, known for its Mediterranean-inspired dishes. Then, explore the Field Museum and learn about natural history.
Afternoon
Enjoy a seafood lunch at Gibsons Bar & Steakhouse. Afterward, visit the Shedd Aquarium and the Adler Planetarium.
Evening
For dinner, indulge in a unique dining experience at Girl & the Goat. Afterward, take a nighttime stroll at Navy Pier.
Bedtime
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Historic Railways and Quaint Charm
Morning
Arrive in Bowling Green, Kentucky, and have a southern-style breakfast at Boyce General Store. Then, visit the Historic RailPark and Train Museum.
Afternoon
Enjoy a BBQ lunch at Smoke Shack BBQ. Spend the afternoon exploring the National Corvette Museum.
Evening
For dinner, try the local favorite, Home Cafe & Marketplace. Take a relaxing walk around the charming downtown area.
Bedtime
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Nature and Heritage
Morning
Start your day with a hearty breakfast at White Squirrel Brewery. Then, head to Mammoth Cave National Park for a guided cave tour.
Afternoon
Have a picnic lunch at the park. Afterward, visit the Ashland The Henry Clay Estate.
Evening
Enjoy a dinner at 440 Main in downtown Bowling Green. Take a leisurely evening walk in a local park.
Bedtime
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Gateway to the West
Morning
Arrive in St. Louis and have a classic St. Louis breakfast at Rooster. Then, visit the iconic Gateway Arch.
Afternoon
Enjoy a lunch at Bogart's Smokehouse. Afterward, explore the City Museum, a unique and interactive art installation.
Evening
Dine at The Shaved Duck for a taste of local BBQ. Take a relaxing evening stroll in Forest Park.
Bedtime
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Historic and Cultural Exploration
Morning
Start your day with a delicious breakfast at The Mud House. Then, visit the Campbell House Museum to learn about St. Louis's history.
Afternoon
Enjoy a leisurely lunch at Baileys' Range. Spend the afternoon at the Missouri Botanical Garden.
Evening
For dinner, try the local favorite, Blueberry Hill. Afterward, explore the Delmar Loop area.
Bedtime
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Family Fun and Entertainment
Morning
Have a family-friendly breakfast at Crown Candy Kitchen. Then, visit the St. Louis Zoo in Forest Park.
Afternoon
Enjoy a casual lunch at Three Sixty. Spend the afternoon at the Citygarden, an urban sculpture park.
Evening
Dine at Charlie Gitto's on the Hill for authentic Italian cuisine. Take a twilight river cruise on the Mississippi.
Bedtime
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Music and History
Morning
Start your day with a soulful breakfast at Southern. Then, visit the National Blues Museum.
Afternoon
Enjoy a BBQ lunch at Pappy's Smokehouse. Spend the afternoon at the Cahokia Mounds State Historic Site.
Evening
For dinner, try the local favorite, Bogart's. Afterward, explore the The Pageant for live music.
Bedtime
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Riverfront and Culinary Delights
Morning
Have a leisurely breakfast at Cafe Osage. Then, take a riverfront walk and visit the Old Courthouse.
Afternoon
Enjoy a seafood lunch at Broadway Oyster Bar. Spend the afternoon at the Campbell House Museum.
Evening
Dine at Revolution for a modern dining experience. Take a sunset river cruise.
Bedtime
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Art and Architecture
Morning
Start your day with a French-inspired breakfast at Brasserie by Niche. Then, visit the City Museum.
Afternoon
Enjoy a leisurely lunch at The Fountain on Locust. Spend the afternoon at the Laumeier Sculpture Park.
Evening
Dine at Sardella for a contemporary Italian meal. Take a nighttime stroll in the Grand Center Arts District.
Bedtime
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Parks and Recreation
Morning
Have a picnic breakfast at Tower Grove Park. Then, visit the Missouri Botanical Garden.
Afternoon
Enjoy a casual lunch at Bluewood Brewing. Spend the afternoon at the St. Louis Science Center.
Evening
Dine at Elmwood for a farm-to-table experience. Take a moonlight bike ride in Forest Park.
Bedtime
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Final Day in St. Louis
Morning
Enjoy a hearty breakfast at Cafe Madeleine. Then, take a self-guided walking tour of the Soulard Historic District.
Afternoon
Have a late lunch at Baileys' Chocolate Bar. Spend the afternoon at the Anheuser-Busch Brewery.
Evening
For your final dinner in St. Louis, savor the flavors of Farmhaus. Conclude your trip with a visit to the Top of the Riverfront for a farewell drink with a view.
Bedtime
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Departure Day
Morning
On your departure day, enjoy a relaxed breakfast at Cafe Ventana. Take a morning walk in Forest Park before heading to the airport for your flight home.
Afternoon
Evening
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