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5-Day Chicago and Great Lakes Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Icons and River Cruise
Morning
Start your Chicago adventure with a delicious breakfast at Miller's Pub, a historic gastropub in the heart of the city. Afterward, take a stroll along the iconic Chicago Riverwalk to admire the architecture and the morning hustle of the city.
Afternoon
For lunch, head to The Gage, known for its upscale American cuisine. Post-lunch, enjoy a comprehensive tour of the city with the Chicago Big Bus Hop-on Hop-off Open-Top Sightseeing Tour. Hop off at the Magnificent Mile for some world-class shopping and explore the nearby Wrigley Building and Tribune Tower.
Evening
Dine at Cindy's Rooftop, offering stunning views of Millennium Park. After dinner, experience the city from above at the 360 Chicago Observation Deck Sip and View Ticket with a drink in hand.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.28Chicago Big Bus Hop-on Hop-off Open-Top Sightseeing Tour
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4.28Chicago Big Bus Hop-on Hop-off Open-Top Sightseeing Tour
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Museum Marvels and Navy Pier
Morning
Enjoy a hearty breakfast at Lockwood Restaurant & Bar before immersing yourself in science and history at the Museum of Science and Industry. Explore the museum at your own pace or opt for a VIP tour.
Afternoon
Grab a quick bite at South Branch Tavern & Grille (The Loop - Chicago) and then head to the Navy Pier. Use your Chicago Navy Pier Centennial Wheel Regular & Express Ticket to take a spin and enjoy the pier's attractions.
Evening
Indulge in a gourmet dinner cruise on Lake Michigan with the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Savor the flavors of the city while taking in the stunning skyline from the water.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.48Navy Pier
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4.48Navy Pier
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Culinary Delights and Evening Entertainment
Morning
Start your day with a delightful brunch at Plymouth Restaurant & Rooftop Bar. Post-brunch, take a guided Chicago Favorite Foods Guided Walking Tour to sample a variety of local dishes and learn about the city's culinary scene.
Afternoon
After the tour, explore the vibrant neighborhood of Wrigleyville and visit the historic Wrigley Field. Grab a snack at the nearby Five Star Bar before heading to the Lincoln Park & Zoo for a leisurely afternoon.
Evening
For dinner, experience the speakeasy vibe at Untitled Supper Club. End the night with a live performance at the iconic Chicago Theatre or enjoy some laughs at a local comedy club.
Bedtime
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4.82Chicago Favorite Foods Guided Walking Tour
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4.82Chicago Favorite Foods Guided Walking Tour
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4.86Wrigley Field
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4.86Wrigley Field
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Architectural Wonders and Ghostly Tales
Morning
Fuel up for the day with breakfast at Reviver. Then, embark on the highly-rated Chicago River 1.5-Hour Guided Architecture Cruise to witness the city's famous skyline and learn about its impressive buildings.
Afternoon
Enjoy a guided Chicago Gangsters and Ghosts Guided Walking Tour through the city's darker history. For lunch, stop by Fadó Irish Pub for some traditional Irish fare.
4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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Cultural Immersion and Farewell Feasts
Morning
Begin your day with breakfast at LUXBAR, a popular spot for its classic American dishes. Then, explore the Art Institute of Chicago, home to a world-class collection of art spanning centuries and continents.
Afternoon
For lunch, head to Bar Siena for some Italian flavors. Post-lunch, visit the Field Museum and immerse yourself in natural history and anthropology. Alternatively, you can opt for a VIP tour experience.
Evening
Conclude your Chicago journey with a memorable dinner at Emerald Loop Bar & Grill, offering a diverse menu in a casual, friendly atmosphere. Raise a glass to the fantastic time you've had in the Windy City.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.56Field Museum
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4.56Field Museum
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