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Roam Around

5 Days Exploring Chicago Illinois Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to the iconic Millennium Park. Take a leisurely stroll and admire the famous Cloud Gate sculpture, also known as 'The Bean.' For breakfast, head to The Bongo Room, known for its creative pancakes and brunch dishes.

Afternoon

In the afternoon, explore the fascinating exhibits at the Art Institute of Chicago, one of the oldest and largest art museums in the United States. For lunch, enjoy a meal at The Gage, an upscale tavern offering hearty American fare.

Evening

Spend your evening at House of Blues, where you can enjoy live music and a vibrant atmosphere. For dinner, savor Southern-inspired cuisine at Southern Cut Barbecue.

Bedtime

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4.69
Millennium Park
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4.61
Art Institute of Chicago
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Architectural Marvels and Scenic Views

Morning

Begin your day with a visit to the towering Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in the Western Hemisphere. Enjoy breakfast at Lou Mitchell's, a classic diner known for its hearty breakfasts.

Afternoon

Head over to explore the historic Rookery Building and marvel at its stunning architecture. Then take a walk along the scenic Chicago Riverwalk. Have lunch at Green Street Smoked Meats, famous for its Texas-style barbecue.

Evening

Catch an evening show at the legendary Chicago Theatre, an architectural gem that hosts concerts, comedy shows, and more. Dine nearby at Piccolo Sogno, offering delicious Italian cuisine.

Bedtime

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Skydeck Chicago at Willis Tower (Sears Tower)
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4.73
Rookery Building
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Cultural Gems and Lakeside Fun

Morning

Visit the educational and interactive exhibits at the renowned Field Museum. Start your day with breakfast at Yolk South Loop, known for its creative breakfast dishes.

Afternoon

Explore marine life wonders at the nearby Shedd Aquarium. Afterward, enjoy lunch with stunning lake views at Riva Crabhouse on Navy Pier.

Evening

Spend your evening exploring entertainment options on Navy Pier itself. Enjoy dinner aboard an evening cruise from Navy Pier with Odyssey Cruises for a unique dining experience on Lake Michigan.

Bedtime

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Field Museum
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4.75
Shedd Aquarium
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Sports Enthusiast's Day Out

Morning

Start your morning by visiting historic sports venues like Wrigley Field or Soldier Field. Have breakfast nearby at Ann Sather Restaurant & Catering known for their cinnamon rolls.

Afternoon

Evening