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3 Days of Comedy and Live Music in Chicago Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Stroll through the park and take in the famous Cloud Gate sculpture (also known as 'The Bean'). The park is a great place to relax and enjoy some green space in the middle of the city.

Afternoon

Head over to Art Institute of Chicago for an afternoon immersed in art and culture. This world-renowned museum houses an extensive collection of artworks from various periods and regions. Don't miss the Impressionist and Post-Impressionist paintings. For lunch, enjoy a meal at The Purple Pig, known for its delicious Mediterranean-inspired dishes.

Evening

In the evening, catch a live comedy show at Second City, one of Chicago's most famous comedy clubs. Many famous comedians have started their careers here, so you're guaranteed a night full of laughs. For dinner, head to Girl & the Goat, a highly-rated restaurant offering innovative small plates.

Bedtime

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Millennium Park
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Art Institute of Chicago
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Cultural Gems and Nightlife

Morning

Begin your day with a visit to Chicago Cultural Center. This stunning building offers free art exhibits and cultural events throughout the year. It's also home to the world's largest Tiffany stained-glass dome.

Afternoon

After exploring the Cultural Center, take a walk along Chicago Riverwalk. This scenic pathway along the Chicago River offers beautiful views of the city's architecture. Stop for lunch at Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.

Evening

Spend your evening enjoying live music at House of Blues. This iconic venue hosts performances by both well-known artists and up-and-coming musicians across various genres. Before heading to the show, have dinner at Joe's Seafood, Prime Steak & Stone Crab, renowned for its fresh seafood and prime steaks.

Bedtime

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Chicago Cultural Center
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Chicago Riverwalk
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Skyline Views and Sports Fun

Morning

Kick off your day with breathtaking views from Skydeck Chicago at Willis Tower (Sears Tower). The observation deck offers panoramic views of Chicago's skyline from one of its tallest buildings.

Afternoon

In the afternoon, explore historic sports venues by visiting Wrigley Field, home to the Chicago Cubs. Even if it's not baseball season, you can take a guided tour to learn about this iconic stadium's history. For lunch nearby, try some deep-dish pizza at Pequod's Pizza, famous for its caramelized crust.

Evening

Wrap up your trip with an evening visit to Navy Pier. Enjoy rides, games, shops, and restaurants along this bustling pier on Lake Michigan. Have dinner at The Signature Room at the 95th located in John Hancock Center; it offers fine dining with spectacular views.

Bedtime

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