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Ultimate 5-Day Chicago Adventure

Ultimate 5-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks

Morning
Start your day with a delicious breakfast at Lou Malnati's Pizzeria to fuel up for a busy day. Then, head to the iconic Willis Tower Skydeck and The Ledge for breathtaking views of the city.
Afternoon
After taking in the city from above, grab a quick lunch at Portillo's Hot Dogs before embarking on a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's stunning architecture.
Evening
For dinner, indulge in the gourmet offerings at Gibsons Bar & Steakhouse. Afterward, take a leisurely stroll along the Chicago Riverwalk to enjoy the city lights.
Bedtime
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Museums and Science

Morning
Enjoy a hearty breakfast at The Signature Room at the 95th before immersing yourself in the wonders of the Museum of Science and Industry.
Afternoon
For lunch, savor the flavors of Italy at Eataly Chicago. Then, continue your cultural exploration with a visit to the Art Institute of Chicago.
Evening
End your day with a delightful dinner at Girl & The Goat, known for its innovative cuisine. Afterward, unwind with a nightcap at the 360 Chicago Observation Deck Sip and View.
Bedtime
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Chicago's Culinary Scene

Morning
Start your day with a scrumptious brunch at Lula Cafe. Then, explore the vibrant neighborhood of Wicker Park and Bucktown.
Afternoon
For lunch, head to Big Star for some delicious tacos. Afterward, take a guided tour to discover the city's mob and crime history with the Chicago Mob and Crime Bus Tour.
Evening
Enjoy a memorable dinner at Kuma's Corner, known for its unique burgers. Afterward, experience the lively nightlife in the area.
Bedtime
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Lakefront and Parks

Morning
Start your day with a refreshing breakfast at Little Goat Diner. Then, take a leisurely stroll through the beautiful Millennium Park and enjoy the iconic Cloud Gate (The Bean).
Afternoon
For lunch, try the mouthwatering dishes at The Purple Pig. Then, visit the serene Lincoln Park & Zoo and enjoy the greenery and wildlife.
Evening
End your day with a delightful dinner at RPM Italian. Afterward, take a relaxing evening walk along the Chicago Lakefront Trail.
Bedtime
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Navy Pier and Beyond

Morning
Enjoy a delightful breakfast at Cafe Ba-Ba-Reeba!. Then, head to the iconic Navy Pier and take a ride on the Centennial Wheel for stunning views of the city.
Afternoon
For lunch, indulge in the flavors of Spain at The Purple Pig. Then, explore the interactive exhibits at the Chicago Museum of Science and Industry.
Evening
End your trip with a memorable dinner at Au Cheval, known for its famous burger. Afterward, take a relaxing evening walk along the Chicago Riverwalk to soak in the city's atmosphere.
Bedtime
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