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Ultimate 10-Day Chicago Exploration Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks
Morning
Start your Chicago adventure with a delicious brunch at Lula Cafe, known for its vibrant atmosphere and farm-to-table dishes. Afterward, head to Millennium Park to see the famous Cloud Gate, also known as "The Bean," and take a leisurely walk around the park.
Afternoon
For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Afterward, visit the Art Institute of Chicago and spend the afternoon exploring its world-class art collection.
Evening
End your day with a delightful dinner at The Purple Pig, known for its Mediterranean-inspired small plates. After dinner, take a stroll along the Chicago Riverwalk and enjoy the beautiful city lights.
Bedtime
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Lakefront and Skyline Views
Morning
Enjoy a scenic breakfast at The Publican, known for its rustic fare and extensive beer selection. After breakfast, take a bike ride along the Lakefront Trail and soak in the stunning views of Lake Michigan.
Afternoon
For lunch, savor the flavors of Mexico at Xoco, a restaurant by award-winning chef Rick Bayless. Afterward, visit the Adler Planetarium and enjoy the interactive exhibits.
Evening
Dine at The Signature Room at the 95th for dinner and experience panoramic views of the city. After dinner, take a sunset cruise on Lake Michigan for a different perspective of the skyline.
Bedtime
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Cultural Immersion in Chicago
Morning
Start your day with a hearty breakfast at Au Cheval, famous for its indulgent burgers and a must-visit in Chicago. After breakfast, visit the Museum of Contemporary Art and explore the cutting-edge works of art.
Afternoon
For lunch, enjoy a taste of Spain at Cafe Ba-Ba-Reeba!, known for its authentic tapas. Afterward, take a guided tour of the Chicago Theatre and learn about its rich history.
Sports and Outdoor Fun
Morning
Enjoy a classic Chicago breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Afterward, visit Wrigley Field and take a guided tour of this historic baseball stadium.
Afternoon
For lunch, head to Big Star for some of the best tacos in the city. Afterward, spend the afternoon at the Lincoln Park Zoo, one of the oldest zoos in the country.
Evening
Have a casual dinner at Kuma's Corner, a rock music-themed burger joint. After dinner, take a walk along North Avenue Beach and enjoy the views of the city skyline.
Bedtime
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Museum and Science Day
Morning
Start your day with a quick breakfast at Portillo's Hot Dogs, a Chicago institution. Then, visit the Museum of Science and Industry and spend the morning exploring its fascinating exhibits.
Afternoon
For lunch, enjoy some authentic barbecue at Smoque BBQ. Afterward, take a water taxi to the Museum Campus and visit the Shedd Aquarium.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. After dinner, take a night walk on the Chicago Riverwalk.
Bedtime
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Shopping and Magnificent Mile
Morning
Start your day with a delightful breakfast at Little Goat Diner, known for its creative take on classic diner dishes. Then, spend the morning shopping on the Magnificent Mile.
Afternoon
For lunch, enjoy a casual meal at Pequod's Pizza, famous for its caramelized crust. Afterward, visit the 360 Chicago Observation Deck and experience the TILT.
Evening
Dine at Girl & The Goat, a popular restaurant with a focus on bold flavors. After dinner, take a stroll through the historic Water Tower Place.
Bedtime
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Relaxation and Entertainment
Morning
Enjoy a leisurely breakfast at Longman & Eagle, known for its farm-to-table fare. Afterward, spend the morning at the Chicago Riverwalk, taking in the sights and sounds of the city.
Afternoon
For lunch, try the famous Italian dishes at RPM Italian. Afterward, visit the Navy Pier and take a ride on the Centennial Wheel.
Evening
Have a fun evening at a drive-in movie theater and enjoy a unique cinematic experience. Grab some snacks and enjoy a movie under the stars.
Bedtime
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Historic Chicago and Culinary Delights
Morning
Start your day with a classic Chicago breakfast at Wildberry Pancakes and Cafe. Then, take a guided walking tour of the city's historic sites, including the Tribune Tower and the Wrigley Building.
Afternoon
For lunch, indulge in a gourmet experience at Alinea, known for its innovative and artistic dishes. Afterward, take a food tasting walking tour and sample a variety of local flavors.
Evening
Dine at Girl & The Goat, a popular restaurant with a focus on bold flavors. After dinner, take a stroll through the historic Water Tower Place.
Bedtime
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Final Day of Exploration
Morning
Enjoy a relaxed breakfast at Lula Cafe, known for its vibrant atmosphere and farm-to-table dishes. Afterward, take a guided architecture cruise on the Chicago River and learn about the city's iconic buildings.
Afternoon
For lunch, savor the flavors of Italy at Eataly Chicago, a vibrant marketplace with a variety of dining options. Afterward, visit the Willis Tower Skydeck and experience "The Ledge."
Departure Day
Morning
On your last morning in Chicago, enjoy a farewell breakfast at The Purple Pig, known for its Mediterranean-inspired dishes. Take a final walk around the city and soak in the vibrant atmosphere before heading to the airport for your departure.
Afternoon
Evening
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