Windy City Wonders: Your Ultimate Chicago Travel Guide

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Advisor - Raven Gairy
Curated By

Raven Gairy

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Chicago

  • History

  • Architecture

  • Local Culture

Advisor - Windy City Wonders: Your Ultimate Chicago Travel Guide
Curator’s statement

Chicago holds a special place in my heart because of its vibrant culture, iconic architecture and rich history. The Windy City's diverse neighborhoods and lively arts scene offer endless adventures and discoveries. From the stunning skyline to the soulful jazz music, Chicago's unique charm always leaves me inspired and in awe.

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Where to stay in Chicago

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Things to do in Chicago

  • DuSable Black History Museum: This museum is dedicated to the preservation and celebration of African American history, culture and art. It's one of the oldest institutions of its kind in the US and offers a wide range of exhibits and educational programs.

  • Chicago Architecture Center River Cruise: This cruise offers a unique perspective on Chicago's world-renowned architecture. Knowledgeable scholars guide visitors through the history and design of over 50 buildings along the Chicago River.

  • Navy Pier: A 50-acre waterfront destination with amusement rides, restaurants, shops and entertainment venues. It's a popular spot for both tourists and locals, offering stunning views of Lake Michigan and the Chicago skyline.

  • Willis Tower: Formerly known as the Sears Tower, it's one of the tallest buildings in the Western Hemisphere. The Skydeck offers breathtaking views of the city, and the glass-floored "Ledge" allows visitors to look straight down to the street below.

  • Millenium Park: This iconic park is home to famous landmarks like the Cloud Gate sculpture ("The Bean"), the Jay Pritzker Pavilion and the Crown Fountain. It hosts outdoor concerts, art installations and recreational activities.

  • Chicago History Museum: This museum offers a comprehensive look at the history of Chicago and its people. It features a wide range of exhibits, artifacts and interactive displays covering everything from the city's founding to its role in major historical events.

  • Wrigley Field: One of the oldest and most iconic baseball stadiums in the US, it's home to the Chicago Cubs. Known for its ivy-covered outfield walls, historic scoreboard and vibrant game-day atmosphere.

  • Lincoln Park Zoo: This free zoo is one of the oldest in the country and is home to a diverse collection of animals from around the world. It offers a variety of exhibits, educational programs and conservation initiatives.

Places to eat & drink in Chicago

  • Raised: Known for its vibrant atmosphere and creative cocktails, Raised is a favorite spot for nightlife enthusiasts.

  • Beatrix: This all-day dining spot offers a mix of comfort food with a healthy twist, along with a cozy ambiance and friendly service.

  • Petterino’s: Located in Chicago's Theatre District, Petterino’s is a beloved spot for pre-theater dining, offering classic Italian fare and a charming, historic setting.

  • The Walnut Room: This locally owned bar and restaurant in Des Moines is praised for its delicious, gourmet-style sandwiches and fresh, locally sourced ingredients.

  • The Fillmore: Known for its live music and great food, it is a popular venue for music lovers and foodies alike.

  • Roanoke Restaurant: This restaurant is celebrated for its innovative dishes and welcoming atmosphere, making it a go-to spot for food enthusiasts.

  • The Dearborn: A favorite for its upscale dining experience and elegant ambiance, The Dearborn is perfect for special occasions and fine dining.

  • Land & Lake Kitchen: This restaurant is known for its farm-to-table approach, offering fresh, seasonal ingredients and a cozy, rustic atmosphere.

  • Roof on the Wit: Offering stunning views and a chic rooftop setting, it is a popular choice for a memorable dining experience.

  • Canal Street Eatery: This eatery is loved for its diverse menu and vibrant atmosphere, making it a great spot for casual dining and social gatherings.

Advisor - Raven Gairy

Travel Advisor

Raven Gairy

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For more inspiration and insider recommendations, visit our Chicago page.