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Ultimate 5-Day Chicago Exploration Itinerary Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and River Cruises
Morning
Start your Chicago adventure with a hearty breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll to the Chicago Riverwalk to enjoy the morning views and architecture.
Afternoon
For lunch, head to The Purple Pig, where you can indulge in a variety of artisanal cheeses and charcuterie. Spend your afternoon soaring above the city at the Chicago Willis Tower Skydeck and The Ledge Ticket, experiencing the breathtaking views and heart-pounding glass balconies.
Evening
Dine at The Signature Room at the 95th and enjoy a gourmet meal with stunning panoramic views of the city. End your day with a relaxing Chicago 45-Minute Family-Friendly Architecture River Cruise, learning about Chicago's famous architecture.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.41Chicago Willis Tower Skydeck and The Ledge Ticket
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4.41Chicago Willis Tower Skydeck and The Ledge Ticket
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Museums and Lake Michigan
Morning
Start with a delicious breakfast at Au Cheval, known for its mouthwatering burgers. Then, immerse yourself in art and history at the Art Institute of Chicago with a Fast-Pass ticket, allowing you to explore the renowned collections with ease.
Afternoon
Enjoy a leisurely lunch at Giordano's, famous for its stuffed deep-dish pizza. Afterward, visit the Navy Pier to experience the lakeside entertainment and stunning views of Lake Michigan.
Evening
Savor a dinner at Girl & the Goat, known for its bold flavors and innovative dishes. Cap off the evening with a delightful Lake Michigan cruise and a sumptuous meal on the Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.48Navy Pier
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4.48Navy Pier
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Cultural Delights and Skyline Views
Morning
Start your day with a breakfast at Eataly Chicago, offering a variety of high-quality Italian foods. Then, take a stroll through the vibrant Millennium Park, where you can't miss the famous "Bean" at the Cloud Gate sculpture.
Afternoon
For lunch, head to Xoco and enjoy gourmet Mexican street food. Spend your afternoon at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you'll have a 360-degree view of the city and Lake Michigan.
Evening
Dine at RPM Italian, known for its modern Italian cuisine and stylish ambiance. After dinner, experience the city lights from above with a drink at the Chicago 360 Chicago Observation Deck Sip and View Ticket.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Historical Tours and Culinary Exploration
Morning
Start with a breakfast at The Bongo Room, famous for its creative pancakes and brunch dishes. Then, embark on a journey through Chicago's history with the Chicago Prohibition Speakeasies Bus Tour or Walking Tour.
Afternoon
Enjoy a delightful lunch at Lula Cafe, a neighborhood favorite known for its seasonal and locally-sourced menu. Spend your afternoon exploring the vibrant and diverse neighborhoods of Chicago on a Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus.
Evening
Dine at Big Star, a popular spot for its creative tacos and extensive selection of tequila. End your day with a guided culinary journey through the city's vibrant Chinatown on the Chicago Taste of Chinatown Food Walking Tour.
Bedtime
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4.90Chicago Prohibition Speakeasies Bus Tour or Walking Tour
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4.90Chicago Prohibition Speakeasies Bus Tour or Walking Tour
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4.28Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
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4.28Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
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Nature, Science, and Evening Elegance
Morning
Start with a breakfast at Mindy's HotChocolate, where you can enjoy artisanal pastries and a cup of gourmet hot chocolate. Then, spend your morning exploring the natural world at the Shedd Aquarium and the Field Museum.
Afternoon
For lunch, head to Smoque BBQ and savor some of the best barbecue in the city. Afterward, take a leisurely walk through the beautiful Lincoln Park & Zoo, enjoying the greenery and the animals.
Evening
Dine at Longman & Eagle, a Michelin-starred gastropub known for its innovative menu and extensive whiskey selection. End your trip with a visit to the iconic The Chicago Theatre, where you can take a tour and enjoy a live performance.
Bedtime
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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4.56Field Museum
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4.56Field Museum
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