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3 Days of Comedy and Music in Chicago Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and fresh ingredients. After breakfast, head over to Millennium Park, where you can see the iconic Cloud Gate sculpture (The Bean) and enjoy a leisurely stroll through the park.

Afternoon

For lunch, visit Giordano's to try Chicago's famous deep-dish pizza. Afterward, take a walk along the Chicago Riverwalk, where you can enjoy beautiful views of the city skyline and perhaps even take a boat tour.

Evening

In the evening, dine at The Purple Pig, which offers a variety of Mediterranean-inspired dishes. Then head to Second City for a night of laughter at one of Chicago's most famous comedy clubs.

Bedtime

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Exploring Culture and Cuisine

Morning

Begin your day with breakfast at Lou Malnati's Pizzeria, another iconic spot for deep-dish pizza. Then visit the Art Institute of Chicago, home to an extensive collection of art from around the world.

Afternoon

For lunch, stop by Portillo's Hot Dogs to sample some classic Chicago-style hot dogs. Spend your afternoon exploring the exhibits at the Field Museum, one of the largest natural history museums in the world.

Evening

Enjoy dinner at Alinea, a three-Michelin-star restaurant known for its innovative cuisine. End your evening with live music at House of Blues, where you can enjoy performances by local and national artists.

Bedtime

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Field Museum
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Historic Sites and Nightlife

Morning

Kick off your morning with breakfast at The Signature Room at the 95th, offering stunning views from atop the John Hancock Center. Visit Skydeck Chicago at Willis Tower (Sears Tower) next for breathtaking views from one of the tallest buildings in North America.

Afternoon

Have lunch at Girl & The Goat, known for its inventive small plates. Spend your afternoon visiting historic sites like the Chicago Theatre and taking a stroll down The Magnificent Mile.

Evening

Dine at Bavette's Bar & Boeuf, a stylish steakhouse with an old-school vibe. Conclude your trip with more laughs or live music by visiting another comedy club or music venue in downtown Chicago.

Bedtime

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