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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Exploring the Windy City

Morning
Start your day with a delicious cup of coffee from Intelligentsia Coffee Millennium Park. Afterward, head to Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city. Take in the panoramic sights and snap some photos on "The Ledge."
Afternoon
For lunch, indulge in Mediterranean-inspired dishes at The Purple Pig. Afterward, take a stroll along the Chicago Riverwalk and admire the beautiful architecture and river views.
Evening
Enjoy dinner at Girl & the Goat, known for its innovative small plates and vibrant atmosphere. End the evening with drinks at one of Chicago's speakeasy-style bars like The Violet Hour or Three Dots and a Dash.
Bedtime
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Cultural Delights and Lakefront Views

Morning
Start your day by exploring Millennium Park , home to iconic landmarks such as "The Bean" (Cloud Gate) and Crown Fountain. Visit nearby attractions like the Art Institute of Chicago or take a guided architecture cruise along the Chicago River .
Afternoon
Grab lunch at Au Cheval, famous for its mouthwatering burgers. Afterward, visit Shedd Aquarium to discover an incredible variety of marine life. Alternatively, explore the Field Museum or Adler Planetarium .
Evening
Experience stunning views of the city skyline from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) . Consider having dinner at a restaurant with a view, such as Signature Room at the 95th or Cindy's Rooftop. Alternatively, take a romantic sunset cruise on Lake Michigan .
Bedtime
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Exploring Neighborhoods and Landmarks

Morning
Start your day by visiting iconic landmarks like the Chicago Theatre , Tribune Tower , and Wrigley Building . Explore the vibrant neighborhood of River North and enjoy brunch at one of its trendy restaurants.
Afternoon
Take a stroll along The Magnificent Mile , known for its upscale shops and boutiques. Stop by Marina City to admire its unique architecture. Consider taking a gangsters and ghosts walking tour to learn about Chicago's fascinating history.
Evening
Enjoy dinner at a local favorite like Lou Malnati's Pizzeria or Portillo's. Afterward, head to Navy Pier for entertainment options such as fireworks, live music, or a ride on the Centennial Wheel.
Bedtime
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Museums and Cultural Experiences

Morning
Start your day with breakfast at Yolk or Wildberry Pancakes and Cafe. Visit the Museum Campus area, home to the Field Museum , Shedd Aquarium , and Adler Planetarium . Choose one or two museums to explore in-depth.
Afternoon
Grab lunch at Portillo's or Giordano's for some classic Chicago deep-dish pizza. Spend the afternoon exploring Grant Park and Buckingham Fountain. If you're interested in history, consider taking a mob and crime bus tour .
Evening
Experience breathtaking views of the city skyline during a lakefront gourmet brunch, lunch, or dinner cruise . Indulge in delicious food while enjoying the sights and sounds of Lake Michigan.
Bedtime
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Final Day in the Windy City

Morning
Start your day with a visit to the Chicago River for a scenic river cruise . Learn about the city's architecture and history as you sail along the water. Afterward, explore the neighborhood of Lincoln Park and visit the Lincoln Park Zoo.
Afternoon
Enjoy lunch at Lou Malnati's Pizzeria or try some Chicago-style hot dogs at Portillo's. Spend the afternoon shopping along The Magnificent Mile or visiting unique attractions like the Money Museum or American Writers Museum.
Evening
End your trip with dinner at a trendy restaurant in West Loop, such as Girl & the Goat or Au Cheval. Alternatively, take a sunset cruise on Lake Michigan to bid farewell to the beautiful city of Chicago.
Bedtime
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