Summertime in Chicago offers an abundance of activities that cater to a variety of interests. This year, the first weekend in August was particularly vibrant, as the Windy City played host to both the and the National Association of Black Journalists conference. The city was alive with energy, a perfect backdrop for an entertainment editor like myself.
J.P. Morgan Chase, a sponsor of both events, added an extra layer of exclusivity and enjoyment for its members.
At Lollapalooza, the Chase Sapphire Lounge provided festival-goers with a luxurious escape: an air-conditioned space with a perfect view of the main stage, complete with complimentary appetizers and snacks. This initiative, launched in 2024 as part of , is an editorially driven program designed to elevate Chase Travel’s luxury lodging offerings. It aims to simplify the process for Chase Sapphire Reserve cardmembers to plan, book, and visit some of the most sought-after, hand-selected, and highly vetted hotel properties worldwide.
Even for those who aren’t planning trips around Lollapalooza, it’s never a bad idea to plan a trip to Chicago. Beyond Chi-town’s claim to fame being a musically inclined hub across all genres, the city has a few other standout distinctions, including its renowned architecture, and its diverse culinary scene. Ahead, ESSENCE shares our favorite spots, eat, shop, stay and play.
And remember, even for a southern girl like me, it’s , not soda. In the nation’s third largest city, The Edit by Chase Travel spotlighted properties like downtown Chicago’s , a luxury boutique hotel that also served as the residence for many of the festival’s performing artists. This setting provided numerous star-studded encounters, including a brief sighting of Reneé Rapp and a delightful elevator chat with .
Chase Sapphire Reserve cardmembers receive a range of complimentary benefits when they book through The Edit. For myself, I received a room with a corner view, complimentary breakfast each day at , and a $100 property credit that was able to be used at the hotel bar, and room service. The hotel was just a stone’s throw away from the Chicago based music festival, where everyone from Megan Thee Stallion and Victoria Monét to Skrillex and The Killers and even BigXthaPlug and Killer Mike shared space.
The uniqueness of the Chi-town music festival brings about a level of inclusivity and diversity that’s rarely seen in other music festival cities. On my daily walks to the festival, you see ticket holders walking towards Grant Park, dressed in outfits clad in everything from grunge to glitter. The Chi is renowned for its delicious eats, and the beauty of it all is that there isn’t just one signature style of food.
Thanks to the city’s earliest settlers, the Windy City is an amalgamation of flavors. From deep-dish pizza to Italian beef sandwiches, the culinary scene is diverse and colorful. However, mentioning ketchup on a hot dog is practically sacrilegious here (trust me, I learned the hard way).
With the help of , a dining platform owned by Chase, provided Chase Sapphire cardmembers with a handful of delicious places to dine while in Chicago such as Lou Malnati’s Pizzeria and Cindy’s Rooftop. A true cultural bastion of Chicago’s Black community though, is Harold’s Chicken. Founded in 1950 by Harold Pierce, Harold’s Chicken has grown to become an iconic establishment, beloved for its crispy fried chicken and mouth-watering mild sauce.
Each location has its own unique character, reflecting the neighborhood it serves, making every visit a new experience. For many, a trip to Chicago is incomplete without a stop at Harold’s Chicken. It’s more than just a meal; it’s a culinary institution that embodies the rich history and vibrant culture of Chicago’s South Side.
Whether you’re a local or a visitor, Harold’s offers a taste of community and tradition that is undeniably a must-try when in the city. As a native Texan I could be considered a barbecue snob—but Wilma’s BBQ was a rather impressive smokehouse in the city. From the moment I walked in, the smoky aroma of slow-cooked meats enveloped me.
The ribs were tender and flavorful, with just the right amount of char. But it was the wings at Wilma’s that truly stole the show. Flash-fried to achieve a crispy exterior, and seasoned with lemon pepper, each bite was an explosion of flavor.
The wings were coated in a tangy, slightly spicy sauce that complemented the wings beautifully. It’s a must-visit spot that proves Chicago’s barbecue scene can hold its own, even against the high standards of a Texan palate. Eataly Chicago was a more upscale dining experience but the ideal place to try if you’re looking for upscale Italian eats.
The restaurant is situated as a food hall, with various Italian specialties, from gelato to handmade pastas and wine. Inside the food hall, you’ll find La Pizza & La Pasta, Vino &..
., and Il Patio. At Vino &.
.., try the housemade rosemary focaccia.
The restaurant also has a full bar, however, if you’re like me looking for zero-proof drinks, they have a great selection of mocktails. At La Pizza & La Pasta, the classic lasagne emiliane was a true taste of Italy, with housemade lasagna sheets, pork and beef ragù alla Bolognese. If you find yourself craving something sweet, a stop by Garrett Popcorn will certainly satisfy your craving.
This famed popcorn shop has been a Chicago staple since 1949, known for its irresistible, handcrafted popcorn recipes that have delighted locals and visitors alike for generations. Walking into a Garrett Popcorn shop, you’re immediately greeted by the mouthwatering aroma of fresh popcorn being made. The shop offers a variety of flavors, but the Garrett Mix—a delightful blend of their rich, buttery CaramelCrisp and savory CheeseCorn—is an absolute must-try.
Each kernel is coated to perfection, creating a harmonious blend of sweet and salty that keeps you coming back for more—in fact, I brought two bags back home with me just to savor the taste a little bit more. The beauty of Chicago’s downtown cityscape is that downtown is one of the premier places to shop. Marshall Fields was just a few blocks away from the hotel, as well as other clothing stores such as Primark, Sephora, and Uniqlo.
The city’s unparalleled walkability makes getting to all of these destinations a breeze. One of my core travel rules when visiting different cities is to always find my way to a local record store to do some digging—you never know what gems you’ll stumble upon. In downtown Chicago, it was recommended that I visit Reckless Records.
It’s a predominantly rock and alternative vinyl record shop, however, there was a vast selection of contemporary R&B and hip-hop. I found projects such as the late Mac Miller’s , and Solange Knowles’ 2019 album . But perhaps what felt the most serendipitous to purchase was Chicago native Common’s critically acclaimed album, .
A visit to Chicago wouldn’t be complete without experiencing the city’s Skydeck. This iconic attraction draws thousands of tourists year-round, all eager to capture breathtaking photos and enjoy the most unique and exciting perspective Chicago has to offer. At The Ledge, you’ll find yourself standing on glass-floored balconies that extend 4.
3 feet outside of Willis Tower. With only 1.5 inches of glass separating you from the 103 floors below, it’s an exhilarating experience that showcases the city in a truly unforgettable way.
A visit to the Skydeck was a fulfilling experience. Before I even reached the top, I had the chance to immerse myself in the rich history of this storied city. The journey began with engaging exhibits that detailed Chicago’s remarkable past, from its founding and architectural innovations to its vibrant cultural evolution.
By the time I stepped onto The Ledge, I felt a deep connection to the city below. The awe-inspiring views from 103 floors up were made even more meaningful by the historical context I had gained. Gazing out over the sprawling skyline, I could see the landmarks that have shaped Chicago’s identity, each with its own story to tell.
Upon making it to Chi-town, I quickly realized that Chicagoans take immense pride in their city’s architecture. Downtown is a stunning landscape of gorgeous skyscrapers, each telling its own story through unique design and historical significance. The skyline is a testament to the city’s architectural prowess, making it a paradise for enthusiasts and casual admirers alike.
One of the best ways to truly appreciate Chicago’s architectural beauty is by taking the architecture boat tour. This tour offers an unparalleled perspective of the city’s most iconic buildings from the water, allowing you to see the intricate details and grandeur up close. The experience is both informative and visually captivating, providing a comprehensive history of Chicago’s architectural evolution.
Thanks to Pendry’s amazing concierge, I was able to secure a spot on this highly recommended tour. The concierge not only facilitated the booking but also provided insightful tips to make the most of the experience. As we cruised along the Chicago River, our knowledgeable guide shared fascinating anecdotes about the city’s architectural milestones, from the historic Tribune Tower to the modernist marvels like Aqua Tower.
The boat tour was a highlight of my trip, offering breathtaking views and a deeper understanding of why Chicago is celebrated as a global architectural hub. The combination of history, design, and the serene river setting made it an unforgettable experience that I highly recommend to anyone visiting the city. Walking to the festival each day, I was continually captivated by the city’s street treasures.
Just a block before entering Grant Park, I encountered Millennium Park, a vibrant urban space that brings public art to the forefront. Millennium Park serves as an open-air gallery where art and architecture blend seamlessly into the city’s landscape. From the moment you approach, you’re greeted by striking installations like the Cloud Gate, affectionately known as “The Bean,” with its reflective surface that invites visitors to engage with both the artwork and the skyline.
The park also features the Crown Fountain, an interactive piece that combines art with play, as well as various sculptures and art installations that change with the seasons. Each day, as I walked through this dynamic area, it felt like the city was alive with creativity and culture. Millennium Park not only offers a glimpse into Chicago’s artistic spirit but also serves as a cultural hub that enhances the experience of attending the festival.
The seamless integration of art into the everyday urban environment underscores Chicago’s commitment to celebrating creativity in all its forms, making each visit to the park a unique and enriching experience. The weekend exemplified Chicago’s unique charm and the vibrant cultural scene that continues to attract visitors and professionals alike. Whether you’re a music enthusiast, a journalist, or simply someone seeking a taste of luxury, Chicago in the summer offers a memorable experience filled with excitement and opportunity, and if you just so happen to be a Chase Sapphire card member, you can enjoy even more personalized visit filled with perks that will elevate your stay.
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