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Chicago, Illinois

Ultimate 10-day Trip to Chicago Itinerary

Published: 2023 Oct 25
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Exploring the City's Icons

Morning
Start your day with a delicious breakfast at Au Cheval, known for their mouthwatering burgers and decadent brunch options. Afterward, head to The Magnificent Mile for a shopping spree at the city's premier retail district.
Afternoon
Grab a quick bite at Portillo's Hot Dogs for a classic Chicago-style hot dog. Then, visit the iconic Wrigley Building and take a stroll along the beautiful Chicago Riverwalk. End your afternoon with a visit to the renowned Art Institute of Chicago to admire its impressive collection.
Evening
Indulge in a fine dining experience at Alinea, a three-Michelin-star restaurant known for its innovative and artistic cuisine. Afterward, catch a show at the historic Chicago Theatre for a memorable evening of entertainment.
Bedtime
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Architecture and History

Morning
Start your day with a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's stunning skyline and learn about its architectural marvels. After the cruise, enjoy a delightful brunch at Little Goat Diner, known for its creative twists on classic dishes.
Afternoon
Embark on a Chicago Gangsters and Ghosts 2-Hour Walking Tour to explore the city's notorious past and visit infamous gangster sites. For lunch, savor the flavors of authentic Mexican cuisine at Xoco.
Evening
Experience the vibrant atmosphere of Navy Pier and take a ride on the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for breathtaking views of the city. Enjoy a delicious dinner at The Purple Pig, known for its Mediterranean-inspired small plates.
Bedtime
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Museums and Parks

Morning
Immerse yourself in science and innovation at the Museum of Science and Industry. Explore the museum's fascinating exhibits and interactive displays. For a quick snack, grab a bite at Eataly Chicago, a vibrant Italian marketplace.
Afternoon
Visit the Field Museum to discover the wonders of natural history. Afterward, enjoy a leisurely picnic at Grant Park while taking in the stunning views of Lake Michigan. For dinner, head to Lula Cafe for farm-to-table cuisine.
Evening
Take a relaxing Chicago River Guided Sunset Cocktail & Architecture Tour and enjoy the city's skyline as the sun sets. End your evening with a romantic dinner at Girl & the Goat, known for its inventive and flavorful dishes.
Bedtime
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Sky-high Views and Cultural Gems

Morning
Start your day by visiting the 360 Chicago Observation Deck Skip-the-Line Ticket at the John Hancock Center. Enjoy panoramic views of the city from the 94th floor. For breakfast, grab a coffee and pastry at Lula Cafe.
Afternoon
Explore the vibrant neighborhood of Wicker Park and indulge in a delicious lunch at Big Star, known for its mouthwatering tacos and margaritas. Visit the Chicago Cultural Center, a stunning architectural gem, and immerse yourself in its art exhibitions.
Evening
Experience the lively atmosphere of Wrigley Field by catching a Chicago Cubs baseball game. Enjoy a classic Chicago-style deep-dish pizza for dinner at Lou Malnati's Pizzeria.
Bedtime
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Lakefront Adventures

Morning
Start your day with a refreshing walk along the Chicago Lake Michigan Skyline Tour & Lake Hopper Cruise. Take in the breathtaking views of the city's skyline and enjoy the cool lake breeze. For breakfast, grab a bagel and coffee at Bagel Art.
Afternoon
Visit the Shedd Aquarium to explore the wonders of marine life. Afterward, enjoy a leisurely lunch at The Publican, known for its farm-to-table cuisine and extensive beer selection.
Evening
Take a romantic Chicago 1.5-Hour Romantic Sunset Cruise and admire the city's skyline as the sun sets over Lake Michigan. Indulge in a gourmet dinner at Gibsons Bar & Steakhouse, renowned for its prime steaks and elegant ambiance.
Bedtime
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Cultural Delights

Morning
Start your day with a visit to the Adler Planetarium to explore the wonders of the universe. For breakfast, enjoy a delicious pastry and coffee at Floriole Cafe & Bakery.
Afternoon
Discover the vibrant Mexican culture of Chicago's Pilsen neighborhood on a Chicago Gangsters and Food Tasting Walking Tour. Sample delicious Mexican dishes and learn about the neighborhood's history. For lunch, savor the flavors of authentic Chicago-style deep-dish pizza at Giordano's.
Evening
Immerse yourself in the world of jazz at Green Mill Cocktail Lounge, a historic jazz club known for its live performances. Enjoy a late-night dinner at Kuma's Corner, famous for its gourmet burgers and rock-inspired atmosphere.
Bedtime
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Art and History

Morning
Explore the stunning architecture of Frank Lloyd Wright on a visit to the Frederick C. Robie House in Oak Park, a suburb of Chicago. For breakfast, enjoy a delicious brunch at Berwyn's Cafe.
Afternoon
Visit the Chicago History Museum to learn about the city's rich history and culture. For lunch, indulge in mouthwatering barbecue at Smoque BBQ.
Evening
Take a leisurely stroll through the picturesque Lincoln Park and visit the Lincoln Park Zoo. Enjoy a delightful dinner at Longman & Eagle, known for its innovative American cuisine and extensive whiskey selection.
Bedtime
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Neighborhood Exploration

Morning
Start your day with a visit to the charming neighborhood of Andersonville. Explore the unique shops and boutiques, and enjoy a delicious breakfast at Hopleaf Bar.
Afternoon
Discover the vibrant food scene of Chicago's West Loop neighborhood on a Chicago Food, History and Architecture Tour with Tastings. Sample a variety of culinary delights and learn about the neighborhood's history. For lunch, savor the flavors of gourmet burgers at Au Cheval.
Evening
Enjoy a craft beer tasting experience at Revolution Brewing and indulge in a delicious dinner at their brewpub.
Bedtime
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Parks and Recreation

Morning
Start your day with a visit to the beautiful Millennium Park. Take a selfie at the famous Chicago Bean and enjoy the stunning outdoor art installations. For breakfast, grab a coffee and pastry at Intelligentsia Coffee.
Afternoon
Explore the natural beauty of Garfield Park Conservatory and immerse yourself in its lush greenery and exotic plants. For lunch, enjoy a delicious sandwich at Potbelly Sandwich Shop.
Evening
Experience the vibrant nightlife of Chicago's River North neighborhood. Enjoy a cocktail at The Aviary and savor a gourmet dinner at RPM Steak.
Bedtime
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Farewell to Chicago

Morning
Take a leisurely stroll along the beautiful Lakefront Trail and enjoy the scenic views of Lake Michigan. For breakfast, grab a delicious pastry at Do-Rite Donuts.
Afternoon
Visit the Chicago Architecture Center to deepen your understanding of the city's architectural heritage. For lunch, savor the flavors of authentic Chicago-style pizza at Pequod's Pizza.
Evening
End your trip with a memorable dinner at Frontera Grill, renowned for its vibrant Mexican cuisine created by celebrity chef Rick Bayless. Raise a glass to an unforgettable time in Chicago at The Violet Hour, a speakeasy-style cocktail bar.
Bedtime
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