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Roam Around

4 Days in Chicago from Dallas Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to the iconic Millennium Park, home to the famous Cloud Gate sculpture. This park is a must-see for its beautiful gardens and art installations. Enjoy breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and fresh ingredients.

Afternoon

Head over to the Art Institute of Chicago to explore one of the oldest and largest art museums in the United States. For lunch, dine at The Gage, which offers upscale American cuisine right across from Millennium Park.

Evening

In the evening, take a stroll along the Chicago Riverwalk, a vibrant waterfront area with stunning views of the city skyline. Have dinner at RPM Seafood, which offers exquisite seafood dishes with a view of the river.

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 Sports

Morning

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

Afternoon

Explore more architectural wonders by visiting the historic Rookery Building. For lunch, head to Girl & The Goat, renowned for its innovative dishes and vibrant atmosphere.

Evening

Catch an evening game or concert at the iconic United Center. Before heading there, enjoy dinner at Publican Quality Meats, offering some of the best charcuterie and sandwiches in town.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.73
Rookery Building
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Cultural Gems and Shopping

Morning

Start your day with a visit to the fascinating exhibits at the Field Museum. Have breakfast at Yolk South Loop, famous for its creative breakfast dishes.

Afternoon

Spend your afternoon exploring The Magnificent Mile's shops and landmarks like the historic Wrigley Building. For lunch, stop by The Purple Pig for Mediterranean-inspired small plates.

Evening

In the evening, catch a show at the legendary comedy club, Second City. Before that, have dinner at Frontera Grill, known for its authentic Mexican cuisine.

Bedtime

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4.56
Field Museum
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4.39
Wrigley Building
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Parks and Entertainment

Morning

Begin your final day with a relaxing visit to Lincoln Park & Zoo. This free zoo is perfect for animal lovers. Enjoy breakfast nearby at Toast Lincoln Park, offering delightful brunch options.

Afternoon

Head over to Navy Pier for some afternoon fun. This iconic landmark features rides, shops, and beautiful lake views. Have lunch at Offshore Rooftop & Bar on Navy Pier itself.

Evening

End your trip with an unforgettable experience by attending a live music performance at House of Blues. Before that, savor dinner at Gibsons Bar & Steakhouse, known for its classic American steakhouse fare.

Bedtime

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