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Mother-Daughter Chicago City Escape: Iconic Sights & Local Cuisine

Mother-Daughter Chicago City Escape: Iconic Sights & Local Cuisine Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a leisurely walk to Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean."
Afternoon
For lunch, savor the flavors of Chicago at Lou Malnati's Pizzeria, a renowned spot for deep-dish pizza. Afterward, head to Navy Pier to enjoy a ride on the Centennial Wheel and take in the views of Lake Michigan.
Evening
In the evening, dine at Girl & the Goat, a top-rated restaurant offering a creative menu. After dinner, experience the city from above at the 360 Chicago Observation Deck, especially beautiful at sunset. End the night with a leisurely walk along the Chicago Riverwalk.
Bedtime
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Architectural Marvels and Culinary Delights

Morning
Enjoy a delicious breakfast at Au Cheval, known for its upscale diner fare. Then, embark on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic buildings and history.
Afternoon
For lunch, indulge in a classic Chicago hot dog at Portillo's Hot Dogs. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for more stunning views of the city.
Evening
Conclude your trip with a memorable dinner at Alinea, a three-Michelin-star restaurant offering a unique dining experience. Afterward, take a leisurely stroll along Historic Route 66 in the city, soaking in the nostalgia and charm of this iconic highway.
Bedtime
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