Rolling Out

Experience vibrant Chicago in the summertime

Chicago skyline
Photo credit: Shutterstock.com / Rudy Balasko

Summertime in Chicago is a vibrant tapestry of activities that cater to diverse interests. This August, the city buzzed with excitement as it hosted the Lollapalooza music festival alongside the National Association of Black Journalists conference. The energy was palpable, making it an ideal backdrop for entertainment enthusiasts.


Where to stay: The Pendry

For a luxurious stay, consider The Pendry, a boutique hotel in downtown Chicago. The hotel offers exclusive benefits, including complimentary breakfast and property credits, for its members. The hotel’s location makes it a convenient choice for anyone visiting the city.


Where to eat: Chicago’s culinary delights

Chicago’s culinary scene is as diverse as its culture. Here are some must-try spots:

Harold’s Chicken: An iconic establishment known for its crispy fried chicken and unique mild sauce, representing the rich history of Chicago’s Black community.


Wilma’s BBQ: A smokehouse that impresses with tender ribs and flavorful wings, perfect for barbecue lovers.

Eataly Chicago: An upscale Italian food hall offering handmade pasta and gelato, ideal for a sophisticated dining experience.

Garrett Popcorn: A Chicago staple since 1949, famous for its handcrafted popcorn, particularly the irresistible Garrett Mix.

Where to shop: Discover local gems

Chicago’s downtown is a shopping paradise. Visit Marshall Fields for a variety of stores, or explore Reckless Records for a unique selection of vinyl, including contemporary R&B and hip-hop.

Where to visit: Iconic attractions

No trip to Chicago is complete without visiting:

Skydeck: Experience breathtaking views from the Willis Tower’s glass-floored balconies.

Architecture Boat Tour: Discover the city’s architectural marvels from the water.

Millennium Park: Engage with public art, including the famous Cloud Gate sculpture.

Chicago’s summer charm and vibrant cultural scene make it a must-visit destination. Whether you’re a music lover, a foodie or a culture seeker, the Windy City offers an unforgettable experience filled with excitement.

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