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Summary

This solo travel guide to Chicago offers a perfect blend of iconic sightseeing, cultural exploration, and personal indulgence over a weekend. From architectural marvels and green spaces to luxurious pampering and unique culinary experiences, this itinerary ensures a memorable solo adventure in the Windy City.

🌆 Day 1: Iconic Chicago Exploration

Begin your solo adventure in Chicago by exploring the city's most iconic sights, including an architecture river cruise, a stroll along the Riverwalk, and a visit to Navy Pier.

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🌉 Chicago River

Embark on a narrated boat tour highlighting Chicago's architectural marvels along the river. Learn about the city's history and capture stunning photos of the skyline from different angles.

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Tips

Book a 90-minute tour with Wendella for a comprehensive experience. The solo-friendly nature of these boat tours allows you to freely explore the vessel while taking in the breathtaking views.

🚶‍♂️ Chicago Riverwalk

Immerse yourself in the vibrant outdoor space that offers a plethora of dining, art, and recreational activities. Indulge in a leisurely stroll and savor a delightful lunch at Beat Kitchen on the Riverwalk, where you can relish the perfect solo dining experience with river-facing tables.

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Tips

Enjoy the diverse dining options, from local craft beer to coffee, amidst the scenic beauty of the Riverwalk. Whether you opt for a to-go meal or prefer to dine at a table, the ambiance and people-watching opportunities make it an ideal solo traveler's haven.

Travel Information
🌐   Website: https://www.chicago.gov/city/en/sites/chicagoriverwalk/home.html
🕒   Hours: See hours
⏳   Typical duration: 45 min
📍   Address: 22 E Wacker Dr, Chicago, IL 60601

🎡 Navy Pier

Explore the bustling pier that offers entertainment, dining, and stunning views of Lake Michigan. Take a leisurely walk around the pier, which is always bustling with people, making it a safe and enjoyable spot for solo travelers.

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Tips

Visit the Offshore Rooftop & Bar for a relaxed atmosphere and excellent views over Lake Michigan. Indulge in a refreshing drink or snack while soaking in the picturesque surroundings, creating a memorable solo travel experience.

Travel Information
📞   Phone: (312) 595-7437
🌐   Website: https://navypier.org/
🕒   Hours: See hours
⏳   Typical duration: 3 hours
📍   Address: 600 E Grand Ave, Chicago, IL 60611
🔗   Profiles: Facebook Pinterest X (Twitter) Instagram

🎨 Day 2: Art and Pampering Day

Dedicate your second day to exploring Chicago's green spaces and museums, followed by an afternoon of pampering and a rooftop dinner.

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🏞️ Grant Park

Grant Park is a sprawling urban oasis, home to the iconic Buckingham Fountain and offering stunning views of the Chicago skyline. The North Rose Garden, Maggie Daley Park, and Millennium Park are all accessible from here, providing a serene escape within the bustling city.

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Tips

Start your day with a refreshing morning walk through Grant Park, taking in the beauty of the North Rose Garden and making your way to the impressive Buckingham Fountain.

🖼️ The Art Institute of Chicago

The Art Institute of Chicago stands as one of America's premier art museums, boasting an extensive collection that spans centuries and continents. From iconic masterpieces to contemporary works, this museum offers a captivating journey through the world of art.

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Tips

Consider purchasing a skip-the-line ticket to make the most of your visit, allowing you to immerse yourself in the art without the hassle of waiting in queues.

Travel Information
📞   Phone: (312) 443-3600
🌐   Website: http://www.artic.edu/
🕒   Hours: See hours
⏳   Typical duration: 3 hours
📍   Address: 111 S Michigan Ave, Chicago, IL 60603
🔗   Profiles: Facebook Instagram YouTube TikTok X (Twitter)

🏨 Viceroy Chicago

The Viceroy Chicago is a luxurious haven, featuring a stunning rooftop pool that offers breathtaking views of the city skyline. With comfortable lounging areas and impeccable amenities, it's the perfect place to unwind and indulge in some well-deserved relaxation.

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Tips

Spend your afternoon basking in the tranquility of the rooftop pool, allowing yourself to unwind and rejuvenate amidst the urban splendor.

Travel Information
📞   Phone: +13125862000
🌐   Website: https://www.viceroyhotelsandresorts.com/chicago
📍   Address: 1118 N State St, Chicago, IL 60610
🔗   Profiles: Facebook Instagram

🌆 Day 3: Food, Views, and Gangsters

Your final day in Chicago is a mix of culinary delights, beach time, and a unique evening tour exploring the city's gangster history.

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🍽️ Chicago Food Tour

Indulge in a 4-hour biking tour that covers Chicago's culinary highlights, from the iconic Chicago dogs to the famous deep-dish pizza and local craft beers. This tour allows you to savor the city's flavors while exploring some of the best Chicago neighborhoods, covering roughly 13 miles.

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Tips

The tour starts at 11:30 a.m., so it's advisable to have a light breakfast beforehand to fully enjoy the gastronomic adventure.

🏞️ Lakefront Trail

Immerse yourself in the beauty of the 18-mile-long Lakefront Trail, offering breathtaking views of Lake Michigan and the iconic Chicago skyline. Whether you choose to take a leisurely stroll or a bike ride, this scenic path is the perfect spot for an afternoon of relaxation and appreciation of natural beauty.

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Tips

Don't forget to bring your camera to capture the stunning vistas along the trail.

👻 Gangsters and Ghosts Tour

Embark on a walking tour that delves into the history of The Loop during the Roaring 20s, a time when speakeasies and gangsters were rampant in Chicago. Explore purportedly haunted sites and hear intriguing ghost stories while gaining insights into the city's captivating past.

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Tips

Opt for the 4 p.m. or 8 p.m. tour to add an element of mystery and history to your evening in Chicago.

Travel Information
📞   Phone: (708) 239-8542
🌐   Website: http://www.gangstersandghosts.com/
🕒   Hours: See hours
📍   Address: 71 East W Wacker Dr, Chicago, IL 60601
🔗   Profiles: Facebook