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Ultimate 11-Day Chicago Exploration with Top Attractions and Dining

Ultimate 11-Day Chicago Exploration with Top Attractions and Dining Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning
Start your Chicago adventure with a delicious breakfast at Au Cheval, known for its famous egg-topped burger. Afterward, head to The Magnificent Mile for some upscale shopping and to admire the historic Wrigley Building.
Afternoon
For lunch, savor the deep-dish pizza at Lou Malnati's Pizzeria. Afterward, take a walk to Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean."
Evening
Enjoy a delightful dinner at The Signature Room at the 95th, offering stunning views of the city. End your day with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a panoramic night view of Chicago.
Bedtime
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The Magnificent Mile

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Millennium Park

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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Art and Science in the Windy City

Morning
Indulge in a brunch at Lula Cafe, a local favorite for its farm-to-table dishes. Afterward, explore the world-class exhibits at the Art Institute of Chicago.
Afternoon
For a late lunch, experience the innovative cuisine at Alinea, a three-Michelin-star restaurant. Then, continue your artistic journey at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with the "Sip and View" experience.
Evening
Dine at The Purple Pig, known for its Mediterranean-inspired small plates. Conclude your day with a visit to the Adler Planetarium for a glimpse into the universe.
Bedtime
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Art Institute of Chicago

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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Adler Planetarium

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Culinary Delights and River Cruises

Morning
Start your day with a delightful breakfast at Little Goat Diner, a cozy spot with a creative menu. After breakfast, take a leisurely walk along the Chicago Riverwalk.
Afternoon
Enjoy a lunch cruise with Chicago's First Lady Architecture River Cruise, where you can learn about the city's iconic buildings. After the cruise, visit the Field Museum.
Evening
For dinner, head to Girl & the Goat, a popular restaurant serving bold flavors. Conclude your evening with a Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
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Chicago Riverwalk

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Chicago Architecture Center Cruise on Chicago's First Lady

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Field Museum

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Chicago River Guided Sunset Cocktail & Architecture Tour

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Gangsters, Ghosts, and Gourmet Food

Morning
Enjoy a relaxed breakfast at Big Star, known for its tacos and patio ambiance. Afterward, embark on the Chicago Gangsters and Ghosts Guided Walking Tour.
Afternoon
For lunch, experience the city's food scene on the Chicago Gangsters and Food Tasting Walking Tour. Afterward, visit the Chicago History Museum.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Conclude your day with a Prohibition Speakeasies Bus Tour.
Bedtime
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Chicago Gangsters and Ghosts Guided Walking Tour

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Chicago Gangsters and Food Tasting Walking Tour

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Chicago Prohibition Speakeasies Bus Tour or Walking Tour

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Neighborhood Exploration and Local Eats

Morning
Start your day with a hearty breakfast at Kuma's Corner, a rock music-themed burger joint. Then, take a Chicago Lakefront Neighborhoods Bike Tour to discover the city's diverse communities.
Afternoon
Enjoy a late lunch at Pequod's Pizza, known for its caramelized crust. Afterward, visit the Lincoln Park Zoo.
Evening
For dinner, savor the flavors of Mexico at Xoco, a restaurant by award-winning chef Rick Bayless. After dinner, take a leisurely walk in Lincoln Park.
Bedtime
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Chicago Lakefront Neighborhoods Bike Tour

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Lincoln Park & Zoo

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Lincoln Park & Zoo

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Museum Day and Culinary Experiences

Morning
Have a relaxed breakfast at Longman & Eagle, a Michelin-starred gastropub. Then, spend the morning at the Museum of Science and Industry.
Afternoon
For lunch, enjoy the barbecue at Smoque BBQ, a local favorite. Afterward, visit the Chicago Cultural Center.
Evening
Dine at The Publican, known for its beer selection and pork dishes. Conclude your day with a visit to the Chicago Theatre for a show.
Bedtime
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Museum of Science and Industry

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Chicago Cultural Center

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Chicago Theatre

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Architectural Wonders and Gastronomic Delights

Morning
Start your day with a gourmet breakfast at Alinea, a three-Michelin-star restaurant. Afterward, take the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's skyline.
Afternoon
Enjoy a fine dining experience at Alinea, known for its innovative and multi-sensory dishes. After lunch, visit the Chicago Architecture Center.
Evening
For dinner, indulge in the tasting menu at Alinea. Conclude your day with a Chicago Architecture Boat Tour with Drinks.
Bedtime
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Chicago River 1.5-Hour Guided Architecture Cruise

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Art Institute of Chicago

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Chicago Architecture Boat Tour with Drinks

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Skyline Views and Culinary Journeys

Morning
Begin your day with a delicious breakfast at The Purple Pig, known for its Mediterranean small plates. Afterward, take a Chicago Lake Michigan Skyline Cruise to admire the city from the water.
Afternoon
For lunch, enjoy the seafood at The Publican, a popular spot for oysters and beer. Afterward, visit the Willis Tower Skydeck and The Ledge.
Evening
Dine at The Signature Room at the 95th, offering panoramic views of the city. Conclude your day with a Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
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Chicago Lake Michigan Skyline Cruise

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Chicago Willis Tower Skydeck and The Ledge Ticket

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Chicago River Guided Sunset Cocktail & Architecture Tour

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Culinary Diversity and Cultural Immersion

Morning
Start your day with a leisurely breakfast at Lula Cafe, a neighborhood gem. Then, explore the vibrant neighborhoods of Chinatown and Little Italy.
Afternoon
Enjoy a multicultural lunch at Eataly Chicago, where you can sample Italian delicacies. Afterward, visit the Chicago History Museum.
Evening
For dinner, experience the flavors of Spain at Cafe Ba-Ba-Reeba!, known for its tapas. Conclude your day with a flamenco show at the restaurant.
Bedtime
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Fountains of Bellagio

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Final Day of Exploration and Farewell to Chicago

Morning
Have a classic Chicago breakfast at Portillo's Hot Dogs, known for its hot dogs and Italian beef. Then, take a Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's history.
Afternoon
Enjoy a farewell lunch at Giordano's, famous for its stuffed deep-dish pizza. Afterward, spend your afternoon at the Navy Pier.
Evening
For your last dinner in Chicago, savor the steak at Gibsons Bar & Steakhouse, a favorite among locals and celebrities. Conclude your trip with a ride on the Chicago Navy Pier Centennial Wheel.
Bedtime
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Chicago Prohibition Speakeasies Bus Tour or Walking Tour

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Navy Pier

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Chicago Navy Pier Centennial Wheel Regular & Express Ticket

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Departure Day - Goodbye, Chicago!

Morning
On your departure day, grab a quick breakfast at Xoco before heading to the airport. If time allows, take a final stroll along the Chicago Riverwalk to soak in the city's energy before saying goodbye to Chicago.
Afternoon
Evening
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Chicago Riverwalk

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