The Ultimate Chicago Bucket List
Chicago is a city that pulses with vibrant energy, offering a unique experience for everyone. Take advantage of the city during the 2025 KeHE Holiday Show. Be sure to indulge in classic Chicago foods, take in the award-winning architecture, explore lush gardens, and dive into a dynamic nightlife scene that promises unforgettable evenings. Chicago is a feast for the senses, a place where culture, flavor, and design converge to create a truly unforgettable adventure.
FOOD & DRINK
Chicago’s culinary scene is a glorious mishmash, from the refined plates of Michelin-starred restaurants to the comforting, unpretentious goodness of its legendary dive bars and deep-dish pizza havens. But to truly experience Chicago, dive into its iconic foods: hot dogs and pizza! The Chicago-style hot dog is a masterpiece of toppings and can be found perfected at spots like Portillo’s, The Wieners Circle, Jim’s Original, and Redhot Ranch. Then, engage in the city’s beloved pizza debate and choose your allegiance in the deep-dish war – every spot has its passionate devotees! For dessert, indulge in a slice of Eli’s Cheesecake, get hooked on the sweet-and-salty magic of Garrett’s Garrett Mix popcorn, or cool down with the vibrant, multi-layered delight of The Original Rainbow Cone. Trust us; your taste buds will thank you for this delicious Chicago immersion!
AWARD-WINNING SKYLINE & ARCHITECTURE
Chicago’s skyline isn’t just a backdrop; it’s a living museum of architectural brilliance. To truly appreciate this award-winning urban landscape, embark on an architecture boat cruise along the Chicago River or opt for a guided walking or bus tour that unveils the stories behind these towering structures. For breathtaking panoramic views, visit The Ledge at Skydeck Chicago or the 94th floor of 360 CHICAGO. If looking to venture outside of the city, visit Oak Park and into the world of Frank Lloyd Wright, the American Institute of Architects’ proclaimed greatest American architect. Explore his iconic Home & Studio and the Unity Temple, and witness firsthand the genius that shaped Chicago’s architectural legacy.
OUTDOOR PARKS AND GARDENS
Chicago isn’t just a city of skyscrapers; it’s also a haven for outdoor enthusiasts, boasting stunning parks and gardens that offer a breath of fresh air amidst the urban bustle. The 606, a 2.7-mile elevated park and trail, provides a unique perspective on the city, perfect for biking, running, or a stroll while weaving through diverse neighborhoods and offering pockets of green spaces on the way. Down by the lakefront, the iconic trio of Grant Park, Maggie Daley Park, and Millennium Park beckon with their lush lawns and must-see attractions, most notably the Bean. Whether seeking an active adventure or a peaceful retreat, Chicago’s outdoor spaces offer a welcome escape and a chance to experience the city’s natural beauty.
NIGHTLIFE
There are endless things to experience in the city, especially when it comes to nightlife! Conveniently located three blocks from McCormick place is Reggies, a Near North Side institution. Choose between their lively Music Joint Bar & Grill or the year-round Trainwreck Rooftop Deck. Indulge in signature wood-fired burgers, award-winning wings, and unique, house-made TV dinners. For a different vibe, try VU Rooftop. Perched 22 stories high, this urban oasis offers breathtaking panoramic views and uniquely crafted cocktails. Nestled in the South Loop’s historic Motor Row District, Duneyrr Fermenta Winery and Brewery is a unique urban escape with a diverse selection of handcrafted beers, vineyard ales, and wines, all produced on-site. Finally, Brando’s Karaoke & Cocktail Bar in the Loop is an unparalleled karaoke experience with a massive library of over 300,000 songs. Discover daily specials, happy hour delights, and a thoughtful selection of non-alcoholic options, ensuring there’s something for everyone.
Learn more about KeHE Shows here.