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Roam Around

2 Days of Adventure in Chicago Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

Morning

Start your day with a hearty breakfast at Lou Malnati's Pizzeria, famous for its deep-dish pizza. Afterward, head to Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of the tallest buildings in the world. The Skydeck offers an exhilarating experience with its glass ledge extending out from the building.

Afternoon

For lunch, visit The Purple Pig, known for its creative small plates and vibrant atmosphere. Post-lunch, embark on an adventure with Chicago Full Day Food Walking Tour + FREE Bike/Kayak Rental. This tour not only lets you savor some of Chicago's best food but also includes a bike or kayak rental to explore the city from a unique perspective.

Evening

Dine at Girl & The Goat, one of Chicago's most popular restaurants offering innovative dishes. End your evening with live music at House of Blues, where you can enjoy a mix of blues and rock performances in an iconic venue.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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5.00
Chicago Full Day Food Walking Tour + FREE Bike/Kayak Rental
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Adventure and Culture in Chicago

Morning

Kick off your day with breakfast at Au Cheval, renowned for its decadent burgers and brunch options. Then head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for another stunning view of the city from above. The observation deck also features interactive exhibits that provide insights into Chicago's history and architecture.

Afternoon

Lunch will be at Portillo's Hot Dogs, a must-visit spot for classic Chicago-style hot dogs and Italian beef sandwiches. Afterward, take a stroll along Chicago Riverwalk, where you can enjoy scenic views of the river and city skyline while engaging in various activities like boat tours or kayaking.

Evening

For dinner, make reservations at Alinea, a three-Michelin-star restaurant known for its avant-garde cuisine and unforgettable dining experience. Conclude your trip with a visit to Navy Pier, where you can enjoy rides, games, and fireworks (seasonal) while taking in beautiful views of Lake Michigan.

Bedtime

Find amazing hotels in Chicago, Illinois.