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Ultimate 5-Day Chicago Adventure: Landmarks, Food, and Culture Itinerary
Last updated: 2024 Jun 14Chicago River Cruise & Iconic Skyline Views
Morning
Start your day with a delightful breakfast at Lula Cafe, known for its fresh and creative dishes. Afterward, embark on the Chicago River 1.5-Hour Guided Architecture Cruise, where you'll learn about the city's stunning architecture from the water.
Afternoon
For lunch, head to Pequod's Pizza for their famous deep-dish pizza. Afterward, visit the The Magnificent Mile for some shopping and sightseeing. Don't miss the iconic Wrigley Building and the beautiful Millennium Park.
Evening
Enjoy a delicious dinner at Girl & The Goat, a renowned restaurant offering a unique dining experience. End your evening with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you can enjoy breathtaking views of the city.
Bedtime
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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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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Museums, Parks, and Cultural Delights
Morning
Start your day with a hearty breakfast at Little Goat Diner, known for its comfort food with a twist. Afterward, visit the Art Institute of Chicago with a fast-pass ticket to explore its impressive collection.
Afternoon
For lunch, indulge in the famous Lou Malnati's Pizzeria deep-dish pizza. Spend the afternoon at the Field Museum or take a leisurely stroll through Grant Park.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. Afterward, take a relaxing walk along the Chicago Riverwalk.
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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Gangsters, Ghosts, and Navy Pier Fun
Morning
Start your day with a quick breakfast at Portillo's Hot Dogs, a Chicago classic. Join the Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's darker history.
Afternoon
For lunch, head to Xoco for some delicious Mexican cuisine. Spend the afternoon at Navy Pier, enjoying the Chicago Navy Pier Centennial Wheel Regular & Express Ticket and the various attractions.
Evening
Enjoy a casual dinner at Big Star, known for its tacos and whiskey selection. End your evening with a Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
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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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4.48Navy Pier
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4.48Navy Pier
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Sports, Brews, and City Views
Morning
Start your day with a delicious breakfast at Kuma's Corner, a rock 'n' roll-themed burger joint. Visit the Wrigley Field for a tour or catch a Chicago Chicago Bulls Basketball Game Ticket if there's a game.
Afternoon
For lunch, head to Smoque BBQ for some mouthwatering barbecue. Spend the afternoon on a Chicago Craft Brewery Tour by Barrel Bus to experience the city's vibrant craft beer scene.
Evening
Enjoy a steak dinner at Gibsons Bar & Steakhouse, a Chicago institution. Afterward, take a leisurely walk along the Marina City and enjoy the unique architecture.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.70Chicago Chicago Bulls Basketball Game Ticket
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4.70Chicago Chicago Bulls Basketball Game Ticket
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Culinary Delights and Cultural Gems
Morning
Start your day with a delightful breakfast at Cafe Ba-Ba-Reeba!, known for its Spanish tapas. Visit the Museum of Science and Industry to explore its fascinating exhibits.
Afternoon
For lunch, enjoy a meal at The Purple Pig, offering a variety of Mediterranean-inspired dishes. Spend the afternoon at the Lincoln Park & Zoo or take a walk through the charming neighborhood.
Evening
End your trip with a memorable dinner at Au Cheval, known for its mouthwatering burgers. Afterward, take a stroll through the Tribune Tower and enjoy the city's architectural gems.
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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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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