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Chicago isn’t just back, it’s surging. In episode six of our 10-part Travelzoo Best Bets Series, Dan and Travelzoo Senior Editor and co-host Gabe Saglie sit down with Lisa Nucci of Choose Chicago to map out the experiences and local insights that turn a short visit into a lasting memory.

We explore the South Side’s moment in the spotlight, from the Obama Presidential Center as a powerful new cultural anchor to Hyde Park’s renewed energy, Pullman’s rail legacy, and the DuSable Black History Museum. Then we move through the city’s 77 neighborhoods like a progressive dinner: Argyle’s Southeast Asian flavors, Pilsen and Little Village for tacos and family-run favorites, and the tavern-cut pizza locals swear by. Music lovers get a guide to Chicago’s house roots, the Chosen Few picnic, legendary late nights at the Green Mill and Kingston Mines, and a theater scene that blends Broadway polish with intimate storytelling. When it’s time to slow down, the architecture river cruise offers a fresh way to understand the skyline.

Chicago’s outdoor side shines too, with 26 miles of lakefront beaches, a beautifully designed Riverwalk, cherry blossoms in Jackson Park, and free cultural wins like Pritzker Pavilion concerts and the Lincoln Park Zoo. Rooftops such as Cindy’s and LondonHouse deliver views year-round, paired with a hotel scene that ranges from stylish value to worthy splurges. Add in big-picture momentum—downtown revitalization, airport upgrades, and major new developments—and it’s clear why Chicago earned its place on the 2026 Best Bets list.

Planning a couples escape, multigenerational getaway, or foodie weekend? Lisa shares her perfect Chicago day, from a Green City Market breakfast to jazz late into the night.

New episodes drop every Tuesday, each featuring local experts who bring these Best Bets to life. Become a member at travelzoo.com to access exclusive offers.

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