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Off-the-Beaten-Path Chicago: A Local's 4-Day Exploration Itinerary
Last updated: 2024 Jun 14Hidden Gems and Culinary Delights
Morning
Start your day with a delightful breakfast at Lula Cafe, known for its cozy atmosphere and farm-to-table dishes. Afterward, take a leisurely stroll through the historic neighborhood of Wicker Park, known for its unique shops and street art.
Afternoon
For lunch, savor the flavors of the Mediterranean at Cafe Ba-Ba-Reeba!. Post-lunch, explore the vibrant community of Logan Square, home to independent boutiques and the iconic Milwaukee Avenue.
Evening
Enjoy a memorable dining experience at Longman & Eagle, a Michelin-starred gastropub. After dinner, immerse yourself in the local music scene at a hidden gem like the Green Mill Cocktail Lounge, known for its jazz performances.
Bedtime
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Verde Canyon Railroad
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Art, Architecture, and Neighborhood Charm
Morning
Indulge in a delicious brunch at Little Goat Diner, a favorite among locals for its creative menu. Afterward, spend the morning exploring the eclectic art galleries of Pilsen, a vibrant neighborhood with a rich cultural heritage.
Afternoon
For a unique dining experience, head to Xoco, renowned for its gourmet Mexican cuisine. After lunch, take a leisurely walk through the picturesque streets of Lincoln Park and visit the charming Lincoln Park Zoo.
Evening
Dine at The Publican, a beloved spot for its focus on seasonal ingredients and craft beer. Conclude your day with a visit to the iconic Second City, where you can enjoy world-class comedy performances.
Bedtime
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Red Rock State Park
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Lincoln Park & Zoo
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Lincoln Park & Zoo
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Local History and Hidden Stories
Morning
Start your day with a hearty breakfast at Au Cheval, famous for its decadent burgers. After breakfast, embark on a guided tour of the Chicago Pedway, a hidden network of underground walkways and passages.
Afternoon
Enjoy a late lunch at Smoque BBQ, known for its authentic smoked meats. In the afternoon, delve into the city's past with a visit to the Driehaus Museum, a hidden gem showcasing Gilded Age design.
Evening
For dinner, experience the innovative cuisine of Alinea, a three-Michelin-starred restaurant. Afterward, take a leisurely walk along the Chicago Riverwalk and enjoy the city lights.
Bedtime
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Lake Powell
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Chicago Riverwalk
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Nature, Relaxation, and Farewell to the City
Morning
Enjoy a peaceful morning at Garfield Park Conservatory, a hidden oasis of tropical plants in the city. Afterward, savor a leisurely brunch at Lula Cafe before heading to the Garfield Park to explore the historic grounds.
Afternoon
Spend your final afternoon in Chicago with a visit to the Pullman National Monument, a lesser-known but significant site in the city's history. For a late lunch, enjoy the famous Portillo's Hot Dogs, a local favorite.
Evening
Conclude your trip with a memorable dinner at Girl & the Goat, known for its bold flavors and lively atmosphere. After dinner, take a sunset stroll along the Chicago Lakefront Trail and bid farewell to the city.
Bedtime
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Antelope Canyon
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ByWard Market
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Canadian Museum of History
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