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Ultimate 5-Day Chicago Adventure in May Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks
Morning
Start your Chicago adventure with a delightful breakfast at Lula Cafe, known for its creative dishes and cozy atmosphere. Afterward, head to the famous The Magnificent Mile for some high-end shopping and a leisurely stroll. Don't miss the chance to take a photo at the iconic Wrigley Building.
Afternoon
For lunch, savor the flavors of Italy at RPM Italian, a modern restaurant with a vibrant ambiance. Afterward, visit the Art Institute of Chicago, home to an impressive collection of art from around the world. Take your time exploring the museum's diverse exhibits.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city skyline. Afterward, take a relaxing evening stroll along the Chicago Riverwalk and admire the city lights reflected in the water.
Bedtime
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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4.39Wrigley Building
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4.39Wrigley Building
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Cultural Immersion and Sky-High Views
Morning
Start your day with a hearty breakfast at Lou Malnati's Pizzeria, a Chicago institution known for its deep-dish pizza. Afterward, visit the Field Museum, where you can explore exhibits on natural history and anthropology.
Afternoon
For lunch, head to The Purple Pig, a popular spot for Mediterranean small plates. Afterward, experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Don't miss the thrilling TILT experience.
Evening
Indulge in a dinner at Girl & The Goat, a renowned restaurant offering a creative menu. Afterward, take a leisurely walk around Millennium Park and admire the iconic Cloud Gate sculpture, also known as "The Bean."
Bedtime
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4.56Field Museum
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4.56Field Museum
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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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Lakefront Serenity and Evening Elegance
Morning
Enjoy a relaxing morning at Lincoln Park & Zoo, where you can stroll through the gardens and visit the animals. For breakfast, try the unique offerings at Little Goat Diner, known for its comfort food with a twist.
Afternoon
For lunch, head to Au Cheval, a popular spot for its famous burger. Afterward, take a cruise on Lake Michigan Skyline Cruise and enjoy the picturesque views of the city from the water.
Evening
Dine in style at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, catch a performance at the historic Chicago Theatre, known for its stunning architecture and top-notch entertainment.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.59Lake Michigan Skyline Cruise
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4.59Lake Michigan Skyline Cruise
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Architectural Marvels and Culinary Delights
Morning
Start your day with a breakfast at Portillo's Hot Dogs, a Chicago favorite. Then, embark on a Chicago Architecture River Cruise Skip-the-Line Ticket to learn about the city's iconic buildings.
Afternoon
For lunch, try the authentic Mexican cuisine at Big Star. Afterward, visit the Chicago River and take a leisurely walk along its banks, enjoying the urban oasis.
Evening
Enjoy a dinner at Kuma's Corner, known for its heavy metal-inspired burgers. Afterward, experience the city's nightlife at one of the local bars or lounges in the vibrant neighborhood of Wicker Park.
Bedtime
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4.83Chicago Architecture River Cruise Skip-the-Line Ticket
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4.83Chicago Architecture River Cruise Skip-the-Line Ticket
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4.61Chicago River
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4.61Chicago River
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Culinary Exploration and Farewell to Chicago
Morning
Start your final day with a breakfast at Xoco, a casual spot known for its Mexican street food. Then, take a guided tour of the city's culinary scene with a Chicago Private custom tour with a local guide.
Afternoon
For lunch, enjoy the flavors of Spain at Cafe Ba-Ba-Reeba!, a tapas restaurant with a lively atmosphere. Afterward, visit the Navy Pier and take a ride on the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for panoramic views of the city.
Evening
Conclude your Chicago adventure with a farewell dinner at Eataly Chicago, a vibrant marketplace offering a variety of dining options. Reflect on your trip as you enjoy your meal and prepare for your journey home.
Bedtime
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4.67Chicago Private custom tour with a local guide
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4.67Chicago Private custom tour with a local guide
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4.48Navy Pier
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4.48Navy Pier
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