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Mother-Daughter Labor Day Weekend Getaway in Chicago

Mother-Daughter Labor Day Weekend Getaway in Chicago Itinerary

Last updated: 2024 Jun 14

City Sights and River Cruise Delight

Morning
Start your day with a delightful breakfast at Lou Mitchell's, a classic spot with a retro vibe. Afterward, take a leisurely walk to the Route 66 Sign for a iconic photo opportunity.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, head to The Bean in Millennium Park to admire the iconic sculpture. Continue your afternoon with a visit to Navy Pier and enjoy the festive atmosphere.
Evening
In the evening, embark on the Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city's skyline. After the cruise, have a magical experience at The Magic Parlour, a captivating magic show. End the night with dinner at The Signature Room at the 95th, offering stunning views of the city.
Bedtime
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Visit Historic Route 66 in Chicago
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Route 66 Sign

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Visit Art Institute of Chicago in Chicago
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The Bean

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Hidden Gems and Culinary Delights

Morning
Enjoy a relaxed morning with brunch at The Purple Pig, known for its delicious small plates. Afterward, take a leisurely stroll along the Chicago Riverwalk.
Afternoon
For a unique experience, explore the city's hidden gems with a guided tour. Afterward, have a late lunch at Girl & the Goat, a renowned restaurant with a creative menu. Spend the rest of the afternoon shopping and exploring the boutiques on The Magnificent Mile.
Evening
Conclude your trip with a memorable dinner at Alinea, a three-Michelin-star restaurant offering a multi-sensory dining experience. After dinner, take a leisurely walk around the Wrigley Building and enjoy the city lights.
Bedtime
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Visit Chicago Riverwalk in Chicago
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Chicago Riverwalk

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Visit The Magnificent Mile in Chicago
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The Magnificent Mile

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Adjacent Cities

IndianapolisLouisvilleNashvilleMemphisDallasAustinHouston

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