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Ultimate 10-Day Chicago Exploration with Iconic Sights and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Introduction and Skyline Views
Morning
Start your Chicago adventure with a delightful brunch at Lula Cafe, known for its farm-to-table dishes. Afterward, take a leisurely walk along the iconic Chicago Riverwalk to soak in the city's architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Post that, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of the city.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering not just exquisite cuisine but also a breathtaking view of the city from the 95th floor of the John Hancock Center.
Bedtime
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Chicago Riverwalk
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Art and Culture Immersion
Morning
Indulge in a gourmet breakfast at The Publican, known for its eclectic menu. Then, spend the morning exploring the world-renowned Art Institute of Chicago.
Afternoon
For lunch, experience the unique culinary creations at Alinea, a three-Michelin-star restaurant. Afterward, visit the Field Museum to delve into natural history and anthropology.
Evening
Conclude your day with a pre-theater dinner at Girl & The Goat, a top-rated restaurant, before enjoying a performance at the historic Chicago Theatre.
Bedtime
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Art Institute of Chicago
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Field Museum
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Chicago Theatre
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Lakefront Serenity and Navy Pier Fun
Morning
Start your day with a relaxed breakfast at Little Goat Diner, a favorite spot for comfort food. Then, take a leisurely bike ride along the Lakefront Trail, enjoying the stunning views of Lake Michigan.
Afternoon
Evening
Dine at RPM Italian, known for its modern Italian dishes, and take a stroll along the pier to enjoy the evening lights and entertainment.
Bedtime
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Navy Pier
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Architectural Marvels and River Cruises
Morning
Enjoy a classic Chicago breakfast at Wildberry Pancakes and Cafe, famous for its variety of pancakes. Then, embark on the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings.
Afternoon
Have a casual lunch at Big Star, known for its tacos and whiskey selection. Afterward, visit the Chicago Architecture Center to further explore the city's architectural heritage.
Evening
For dinner, try the famous Italian beef sandwich at Al's Beef. End your day with a Chicago River Guided Sunset Cocktail & Architecture Tour, combining history with a scenic cruise.
Bedtime
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Chicago River 1.5-Hour Guided Architecture Cruise
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Chicago River Guided Sunset Cocktail & Architecture Tour
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Museum and Culinary Delights
Morning
Start your day with a hearty breakfast at Au Cheval, home to one of the best burgers in the city. Then, visit the Museum of Science and Industry, a fascinating institution for all ages.
Afternoon
Enjoy a diverse culinary experience at Eataly Chicago, where you can sample a variety of Italian dishes. After lunch, take a relaxing walk in Grant Park.
Evening
Dine at The Purple Pig, a popular spot for Mediterranean-inspired small plates. Afterward, take a leisurely evening stroll along the Millennium Park to see the famous Cloud Gate sculpture.
Bedtime
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Museum of Science and Industry
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Grant Park
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Millennium Park
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Gangsters, Ghosts, and Local Flavors
Morning
Start your day with a classic Chicago hot dog at Portillo's Hot Dogs. Then, immerse yourself in the city's history with the Chicago Gangsters and Ghosts Guided Walking Tour.
Afternoon
For lunch, enjoy the vibrant atmosphere and seafood at Gibsons Bar & Steakhouse. Afterward, take a self-guided tour of the Chicago Cultural Center, known for its stunning architecture.
Evening
Indulge in a memorable dining experience at Alinea, one of the best restaurants in the world. After dinner, join the Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's clandestine past.
Bedtime
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Chicago Gangsters and Ghosts Guided Walking Tour
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Chicago Cultural Center
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Chicago Prohibition Speakeasies Bus Tour or Walking Tour
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Neighborhood Exploration and Local Brews
Morning
Enjoy a leisurely brunch at Longman & Eagle, a Michelin-starred gastropub. Then, take a guided tour of the Lincoln Park & Zoo.
Afternoon
For lunch, head to Kuma's Corner, a rock music-themed burger joint. Afterward, explore the trendy shops and cafes in the Wicker Park neighborhood.
Evening
Dine at The Publican, known for its extensive beer selection and pork-centric menu. Conclude your day with a craft beer tasting at one of the local breweries in the area.
Bedtime
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Lincoln Park & Zoo
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Sports and Local Eats
Morning
Start your day with a classic Chicago breakfast at Wildberry Pancakes and Cafe. Then, visit the United Center for a tour of the home of the Chicago Bulls and Blackhawks.
Afternoon
For lunch, enjoy the famous Italian beef sandwich at Al's Beef. Afterward, take a self-guided tour of Wrigley Field and the surrounding Wrigleyville neighborhood.
Evening
Dine at Pequod's Pizza for their unique caramelized crust deep-dish pizza. After dinner, experience the local nightlife in the Lakeview or Lincoln Park neighborhoods.
Bedtime
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United Center
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Wrigley Field
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Culinary Tour and Riverfront Dining
Morning
Embark on a culinary adventure with the Chicago Gangsters and Food Tasting Walking Tour, sampling a variety of local dishes.
Afternoon
Enjoy a leisurely lunch at The Purple Pig, known for its Mediterranean-inspired menu. Afterward, take a walk along the Chicago Riverwalk.
Evening
For your final dinner in Chicago, savor the flavors of the city at Girl & The Goat, a renowned restaurant offering a creative menu. Conclude your trip with a Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, enjoying the city's skyline from the water.
Bedtime
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Chicago Gangsters and Food Tasting Walking Tour
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Chicago Riverwalk
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Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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Farewell to the Windy City
Morning
On your last day in Chicago, enjoy a relaxed breakfast at Lula Cafe, reminiscing about your favorite moments in the city. Take a final walk along the Magnificent Mile and do some last-minute shopping.
Afternoon
For lunch, savor the flavors of Spain at Cafe Ba-Ba-Reeba!, known for its tapas and paella. Afterward, visit the Chicago Riverwalk for one last view of the city.
Evening
As a farewell dinner, indulge in a steak at Gibsons Bar & Steakhouse, a Chicago institution. After dinner, take a night cruise on Lake Michigan to see the city lights from the water.
Bedtime
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The Magnificent Mile
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Chicago Riverwalk
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