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Ultimate 6-Day Chicago Adventure with Iconic Landmarks and Culinary Delights

Ultimate 6-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Riverfront Marvels and Sky-High Views

Morning
Begin your Chicago journey with a delightful breakfast at The Green Door Tavern, a historic spot with a cozy atmosphere. Afterward, take a leisurely stroll along the Chicago Riverwalk, admiring the city's architecture and the iconic Wrigley Building.
Afternoon
For lunch, head to The Gage, where you can enjoy a sophisticated meal in a relaxed environment. Post-lunch, experience the city from the water with the Chicago River 1.5-Hour Guided Architecture Cruise. Learn about the history and design of Chicago's famous buildings.
Evening
Cap off your day with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Skip the line and enjoy a drink with a view using your Chicago 360 Chicago Observation Deck Sip and View Ticket. For dinner, savor the flavors at Bar Siena, known for its Italian cuisine and vibrant ambiance.
Bedtime
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Cultural Icons and Navy Pier Fun

Morning
Start your day with a hearty breakfast at Five Star Bar, a local favorite. Then, make your way to the Art Institute of Chicago with your fast-pass ticket. Explore the impressive collections and don't miss the famous "Bean" at Millennium Park nearby.
Afternoon
Enjoy a diverse and satisfying lunch at Burger Bar Chicago. Afterward, take a walk down the vibrant Magnificent Mile and do some shopping. Continue to Navy Pier for an afternoon of entertainment, including the Chicago Children's Museum or a ride on the Centennial Wheel.
Evening
Dine at The Dearborn, offering a modern take on classic American fare. After dinner, if you're up for some laughs, catch a show at the famous The Second City, known for launching the careers of many comedy legends.
Bedtime
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Historic Treasures and Culinary Delights

Morning
Enjoy a delicious breakfast at Lockwood Restaurant & Bar, located in the historic Palmer House. Post-breakfast, take a guided tour of the Chicago Theatre (if available) to learn about its rich history and glamorous architecture.
Afternoon
For lunch, head to Fadó Irish Pub for a warm and welcoming atmosphere. Spend your afternoon exploring the Field Museum, where you can encounter Sue, the largest and most complete T. rex ever discovered.
Evening
Experience the vibrant atmosphere of State Street and enjoy dinner at Sweetwater Tavern & Grille (Michigan Plaza - Chicago). Afterward, take a leisurely walk to Adler Planetarium and enjoy the stunning views of the city skyline and Lake Michigan.
Bedtime
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Neighborhood Charm and Evening Elegance

Morning
Start your day with a delightful breakfast at The Franklin Room, known for its upscale yet comfortable setting. After breakfast, take a morning stroll through the charming streets of Lincoln Park & Zoo, where you can enjoy the greenery and visit the animals.
Afternoon
For lunch, head to House of Blues Restaurant & Bar for a unique dining experience with live music. Afterward, explore the boutiques and cafes of Armitage Avenue and Halsted Street in the Lincoln Park neighborhood.
Evening
Dress up for an elegant evening at The Signature Room at the 95th. Enjoy a sophisticated dinner with panoramic views of the city. Afterward, if you're in the mood for some nightlife, explore the bars and lounges of the Rush and Division Streets area.
Bedtime
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Sports, Science, and Scenic Views

Morning
Grab a quick breakfast at Miller's Pub before heading to the iconic Wrigley Field. Take a guided tour of this historic ballpark and learn about its storied past.
Afternoon
For lunch, visit FireLake Grill House and Cocktail Bar at the Radisson Blu Aqua Hotel. Post-lunch, immerse yourself in the wonders of the Museum of Science and Industry, where you can explore interactive exhibits and even board a real submarine.
Evening
Enjoy a relaxing dinner at The Beetle Bar and Grill, a cozy spot with a diverse menu. Afterward, take a scenic walk or bike ride along the Lakefront Trail and soak in the beautiful views of Lake Michigan and the city skyline.
Bedtime
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Final Flavors and Farewell Landmarks

Morning
Indulge in a sumptuous breakfast at 676 Restaurant & Bar, known for its innovative cuisine and stylish setting. After breakfast, take a morning stroll through the serene Grant Park, also known as "Chicago's front yard."
Afternoon
For your final lunch in Chicago, head to Bar Louie - Printers Row for a laid-back meal with a wide range of options. Afterward, visit the Skydeck Chicago at Willis Tower (Sears Tower) and step out onto The Ledge for a thrilling experience with glass-floored balconies.
Evening
Conclude your Chicago adventure with a gourmet dinner cruise on the Chicago Odyssey Dinner Cruise. Enjoy a luxurious evening on the water, savoring delicious dishes and taking in the glittering skyline.
Bedtime
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