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Roam Around

4 Days of Lollapalooza and Chicago Exploration Itinerary

Last updated: 2024 Jun 14

Lollapalooza Kickoff and Millennium Park

Morning

Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (The Bean) and offers beautiful gardens and public art installations. It's a great way to ease into the vibrant atmosphere of Chicago.

Afternoon

Head over to Grant Park for Lollapalooza. Spend your afternoon enjoying live music from various artists across multiple stages. The festival atmosphere is electric and offers a mix of genres to suit all tastes.

Evening

After an exciting day at Lollapalooza, unwind with dinner at Quartino Ristorante & Wine Bar. This Italian restaurant offers a cozy ambiance and delicious small plates perfect for sharing.

Bedtime

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4.69
Millennium Park
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Art Institute and More Lollapalooza

Morning

Begin your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from around the globe. Take your time exploring the exhibits and don't miss iconic pieces like Grant Wood's American Gothic.

Afternoon

Return to Grant Park for another day at Lollapalooza. Catch more performances from your favorite artists and discover new ones as you navigate through the festival grounds.

Evening

For dinner, head to Joe's Seafood, Prime Steak & Stone Crab, known for its exquisite seafood dishes and prime steaks. It's the perfect place to relax after a full day of music and art.

Bedtime

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4.61
Art Institute of Chicago
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Exploring Chicago's Highlights

Morning

Kick off your morning with a stroll along the Chicago Riverwalk. Enjoy scenic views of the city skyline while walking along this beautifully designed waterfront path.

Afternoon

Spend your afternoon at Lollapalooza in Grant Park. Immerse yourself in more live music performances and soak up the festival vibes.

Evening

Dine at Bavette's Bar & Boeuf, a stylish steakhouse offering classic dishes in an intimate setting. Their cocktails are also highly recommended.

Bedtime

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Chicago Riverwalk
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Final Day of Music and Deep Dish Pizza

Morning

Visit the Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. The glass ledge is not for the faint-hearted but offers an unforgettable experience.

Afternoon

Enjoy your last afternoon at Lollapalooza in Grant Park. Make sure to catch any final performances you don't want to miss before saying goodbye to this incredible festival.

Evening

End your trip with a quintessential Chicago experience by dining at Pizzeria Uno, famous for its deep dish pizza. It's a must-try when visiting Chicago.

Bedtime

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