Travelzoo Best Bets: Where to Go in 2026 with Choose Chicago

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.