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Ultimate 8-day Trip to Chicago Itinerary

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day 1

Exploring the City's Landmarks

Chicago Itinerary - February 28

Morning. Start your day by taking a 1.5-hour guided architecture cruise on the Chicago River [290485]. Marvel at the stunning skyline and learn about the city's iconic buildings. After the cruise, visit the Art Institute of Chicago [3877] to admire its world-class collection.
Afternoon. Head to Millennium Park [1212] and take a selfie at the famous Cloud Gate sculpture, also known as "The Bean." Explore the nearby Grant Park [1207] and enjoy a picnic lunch. In the afternoon, visit the Field Museum [1206] to discover fascinating exhibits on natural history and anthropology.
Evening. For dinner, indulge in a gourmet meal at Alinea, one of Chicago's most renowned restaurants. Afterward, take a stroll along the Chicago Riverwalk [20620] and enjoy the vibrant atmosphere of the city at night.
day 2

Chicago's Architectural Marvels

Chicago Itinerary - February 29

Morning. Start your day with a visit to the Chicago River Architecture Center Cruise on Chicago's First Lady [466232]. Explore the city's architectural wonders while cruising along the river. Afterward, take a walk along The Magnificent Mile [3871] and do some shopping.
Afternoon. Head to the 360 Chicago Observation Deck [1208] for breathtaking views of the city. Enjoy a late lunch at The Purple Pig, known for its delicious Mediterranean-inspired dishes. In the afternoon, take a guided tour of the historic Rookery Building [18483].
Evening. Experience the vibrant nightlife of Chicago by visiting one of the city's speakeasies. Take a Prohibition Speakeasies Bus Tour or Walking Tour [419643] to discover hidden bars and learn about Chicago's bootlegging history.
day 3

Chicago's Cultural Side

Chicago Itinerary - March 1

Morning. Start your day with a visit to the Museum of Science and Industry [1213]. Explore interactive exhibits and learn about scientific discoveries. Afterward, take a stroll through Lincoln Park & Zoo [1211] and enjoy the beautiful surroundings.
Afternoon. Head to the Chicago Cultural Center [8298] and admire its stunning architecture. Grab lunch at Eataly Chicago, a vibrant Italian marketplace with various dining options. In the afternoon, visit the Adler Planetarium [1209] to explore the wonders of the universe.
Evening. Enjoy a relaxing dinner cruise on Lake Michigan with the Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise [276152]. Indulge in a delicious meal while taking in the stunning views of the city skyline.
day 4

Chicago's Gangster History

Chicago Itinerary - March 2

Morning. Start your day with a Chicago Gangsters and Ghosts 2-Hour Walking Tour [234682]. Explore the city's notorious past and visit sites associated with gangsters like Al Capone. After the tour, grab a quick bite at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs.
Afternoon. Embark on the Chicago Mob and Crime Bus Tour [40483] to delve deeper into the city's mob history. Learn about famous gangsters and their activities in Chicago. In the afternoon, visit the Chicago History Museum [Activity ID] to learn more about the city's history.
Evening. Enjoy a delicious dinner at Gibsons Bar & Steakhouse, known for its prime steaks and lively atmosphere. Afterward, explore the vibrant nightlife of Chicago's River North neighborhood.
day 5

Chicago's Food Scene

Chicago Itinerary - March 3

Morning. Start your day with a food, history, and architecture tour with tastings [243137]. Explore Chicago's diverse culinary scene and learn about the city's history. Afterward, visit the Chicago Riverwalk [20620] and enjoy a coffee at a local cafe.
Afternoon. Head to the West Loop neighborhood and have lunch at Girl & the Goat, a popular restaurant known for its creative dishes. Afterward, visit the United Center [22646], home to the Chicago Bulls and Chicago Blackhawks, for a sports experience.
Evening. Enjoy dinner at Little Goat Diner, a trendy spot serving comfort food with a twist. Afterward, explore the vibrant nightlife of the West Loop neighborhood and visit one of the local bars or lounges.
day 6

Chicago's Skyline and Museums

Chicago Itinerary - March 4

Morning. Start your day by visiting the 360 Chicago Observation Deck Sip and View Ticket [384698]. Enjoy panoramic views of the city while sipping on a refreshing drink. Afterward, visit the Chicago River [1219] and take a leisurely walk along its banks.
Afternoon. Head to the Museum of Ice Cream [421097] for a fun and interactive experience. Enjoy sweet treats and immerse yourself in a world of ice cream. In the afternoon, visit the Shedd Aquarium [1210] to explore its diverse marine life.
Evening. For dinner, try Big Star, a popular taqueria known for its delicious tacos and margaritas. Afterward, take a stroll along Navy Pier [1214] and enjoy the stunning views of Lake Michigan.
day 7

Chicago's Neighborhoods

Chicago Itinerary - March 5

Morning. Start your day by exploring the vibrant neighborhood of Wicker Park. Visit local shops, boutiques, and art galleries. Grab breakfast at a cozy cafe in the area.
Afternoon. Head to the historic neighborhood of Hyde Park and visit the Museum of Science and Industry [1213]. Explore its fascinating exhibits and interactive displays. In the afternoon, take a walk through the beautiful campus of the University of Chicago.
Evening. Enjoy dinner at Lula Cafe, a farm-to-table restaurant known for its seasonal dishes. Afterward, explore the nightlife of Wicker Park and visit one of the local bars or live music venues.
day 8

Farewell to Chicago

Chicago Itinerary - March 6

Morning. Start your day with a visit to the Chicago Riverwalk [20620] and enjoy a leisurely stroll along the river. Grab breakfast at a local cafe and savor your last moments in the city.
Afternoon. Head to the neighborhood of Pilsen and explore its vibrant street art scene. Visit local galleries and murals. Enjoy lunch at Xoco, a Mexican street food-inspired restaurant.
Evening. End your trip with a visit to the Skydeck Chicago at Willis Tower [1215]. Experience breathtaking views from the glass-bottomed Skydeck and step onto The Ledge for a thrilling experience. Afterward, enjoy a farewell dinner at The Publican, known for its farm-to-table cuisine.
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