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Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and Sky-High Views
Morning
Start your Chicago adventure with a delightful breakfast at LUXBAR, known for its upscale American cuisine. Afterward, take a stroll down the iconic Magnificent Mile, where you can shop at high-end boutiques and admire the historic Wrigley Building .
Afternoon
For lunch, head to The Gage, located near Millennium Park. Post-lunch, enjoy an immersive experience at the Art Institute of Chicago with a skip-the-line ticket. Spend your afternoon exploring the impressive art collections.
Evening
Dine with a view at Cindy's Rooftop, offering a panoramic vista of the city. Afterward, skip the line and ascend to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a Sip and View ticket, where you can enjoy the city lights and signature cocktails.
Bedtime
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4.65Magnificent Mile
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4.65Magnificent Mile
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Lakefront Serenity and Navy Pier Excitement
Morning
Enjoy a morning coffee at State and Lake Chicago Tavern before heading to the serene Chicago Riverwalk. Take in the views and the morning breeze as you walk along the river.
Afternoon
Have a delightful lunch at Five Star Bar, a local favorite. Afterward, spend your afternoon at the lively Navy Pier, where you have a Regular & Express Ticket for the Centennial Wheel. Explore the pier's attractions and enjoy the waterfront.
Evening
Experience the city's skyline from a different perspective with a Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Indulge in a sumptuous meal with live music and unmatched views of the Chicago Lake Michigan Skyline.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.48Navy Pier
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4.48Navy Pier
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Museum Marvels and Evening Entertainment
Morning
Start your day with breakfast at Old Town Pour House (Old Town - Chicago). Then, immerse yourself in science and industry at the Chicago Museum of Science and Industry with a ticket or VIP tour. Spend your morning exploring the fascinating exhibits.
Afternoon
For lunch, head to Miller's Pub, a Chicago institution. Post-lunch, continue your museum journey at the Field Museum with a skip-the-line ticket. Discover the natural history and cultural artifacts.
Evening
Dine at FireLake Grill House and Cocktail Bar, offering a warm and inviting atmosphere. Afterward, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history and haunted locations.
Bedtime
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4.31Chicago Museum of Science and Industry
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4.31Chicago Museum of Science and Industry
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4.56Field Museum
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4.56Field Museum
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Historic Landmarks and Culinary Delights
Morning
Enjoy a classic breakfast at Billy Goat Tavern (Millennium Park), a Chicago legend. Then, take a guided architecture cruise along the Chicago River with a 1.5-Hour Guided Architecture Cruise. Learn about the city's famous buildings and their stories.
Afternoon
Have lunch at Sweetwater Tavern & Grille (Michigan Plaza - Chicago) and then visit the iconic Wrigley Field for a guided tour. Immerse yourself in the history of this legendary baseball stadium.
Evening
Dine at The Green Door Tavern, a historic speakeasy with a cozy atmosphere. Afterward, enjoy a live performance at the Chicago Theatre with a skip-the-line ticket, and witness the grandeur of this iconic venue.
Bedtime
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4.61Chicago River
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4.61Chicago River
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4.86Wrigley Field
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4.86Wrigley Field
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Parks, Zoos, and Farewell Bites
Morning
Start your day with breakfast at The Beetle Bar and Grill. Then, spend your morning at Lincoln Park & Zoo, enjoying the beautiful greenery and the diverse animal exhibits.
Afternoon
For lunch, head to El Hefe Chicago for a vibrant atmosphere and delicious Mexican cuisine. Afterward, take a leisurely walk through Grant Park and visit the serene Buckingham Fountain.
Evening
Conclude your Chicago journey with a memorable dinner at Burger Bar Chicago, savoring gourmet burgers and a relaxed ambiance. Reflect on your trip as you enjoy your meal, reminiscing about the iconic landmarks and experiences of the Windy City.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.70Grant Park
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4.70Grant Park
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