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7 Days of Chicago Exploration: Museums, Gastronomy, and Lake Michigan Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your Chicago adventure with a delicious brunch at The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture.
Afternoon
For the best views of the city, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory). After taking in the skyline, have a late lunch at The Signature Room at the 95th, a fine dining restaurant with panoramic views.
Evening
In the evening, experience the city from the water with a Chicago River Guided Sunset Cocktail & Architecture Tour. After the cruise, enjoy a dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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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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Museum Day in Chicago
Morning
Enjoy a hearty breakfast at Lou Malnati's Pizzeria, a famous spot for deep-dish pizza. Then, spend the morning exploring the Art Institute of Chicago, home to a world-class art collection.
Afternoon
For lunch, try the iconic Chicago-style hot dogs at Portillo's Hot Dogs. Afterward, visit the Field Museum to learn about natural history and anthropology.
Evening
End your day with a dinner at The Publican, known for its eclectic menu and vibrant atmosphere.
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 Gourmet Delights
Morning
Start your day with a brunch cruise on Lake Michigan with Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Enjoy the views of the city from the water.
Afternoon
After the cruise, embark on a Chicago Gangsters and Food Tasting Walking Tour to explore the city's mobster history and sample some local delicacies.
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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4.67Chicago Gangsters and Food Tasting Walking Tour
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4.67Chicago Gangsters and Food Tasting Walking Tour
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A Day of Sights and Bites
Morning
Have a leisurely breakfast at Lula Cafe, a cozy spot known for its farm-to-table fare. Then, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's architecture.
Afternoon
For lunch, head to Xoco, a restaurant by Rick Bayless known for its gourmet Mexican cuisine. Afterward, visit the Adler Planetarium to explore the wonders of the universe.
4.46Chicago Architecture Center Cruise on Chicago's First Lady
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4.46Chicago Architecture Center Cruise on Chicago's First Lady
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4.61Adler Planetarium
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4.61Adler Planetarium
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Cultural Immersion in the Windy City
Morning
Start your day with a visit to the Chicago Cultural Center, a historic building that hosts art exhibitions and cultural events. Grab a coffee at the center's cafe.
Afternoon
For lunch, try the gourmet sandwiches at Little Goat Diner, a favorite spot of locals and visitors alike. Afterward, explore the Museum of Science and Industry, a fascinating museum with interactive exhibits.
Evening
Dine at Girl & the Goat, a renowned restaurant offering a creative menu with a focus on local and seasonal ingredients.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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Relaxing Day by Lake Michigan
Morning
Enjoy a leisurely brunch at Cafe Ba-Ba-Reeba!, a Spanish tapas restaurant with a lively atmosphere. Then, take a walk or bike ride along the Lake Michigan Skyline Cruise.
Afternoon
Spend the afternoon at Navy Pier, where you can ride the Centennial Wheel and explore the shops and attractions. Have a late lunch at one of the pier's restaurants.
Evening
For dinner, savor the Italian cuisine at RPM Italian, a stylish restaurant with a modern twist on classic dishes.
Bedtime
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4.59Lake Michigan Skyline Cruise
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4.59Lake Michigan Skyline Cruise
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4.48Navy Pier
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4.48Navy Pier
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Farewell to Chicago with Culinary Delights
Morning
On your last day in Chicago, indulge in a decadent breakfast at Au Cheval, famous for its burgers and egg dishes. Take a walk through Millennium Park and see the iconic Cloud Gate sculpture.
Afternoon
For your final meal in the city, enjoy a late lunch at Giordano's for their famous stuffed deep-dish pizza. Spend the rest of the afternoon shopping and exploring the shops along The Magnificent Mile.
4.69Millennium Park
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4.69Millennium Park
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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