Best Urban Adventures
The splurge destination: Hong Kong
When to go: Hong Kong is a popular year-round destination, but late September to early December is ideal for visiting, when the humidity drops—just be aware that you could still experience a typhoon or two!
Sample economy airfare: $1,250 from San Francisco to Hong Kong
The allure: “Exploring this urban jungle is one of the most exhilarating experiences a city enthusiast can have,” Seshadri says. Hong Kong continues to grow vertically at a fast clip to accommodate its ever-increasing population of locals and expats, creating an architectural wonderland of skyscrapers and breathtaking views.
Hong Kong is jam-packed with Michelin-starred restaurants and luxury shopping malls, so visitors can spend countless days wandering this metropolis and still not see it all. Spend a day antiquing on Cat Street, visiting Man Mo Temple or browsing galleries on Tai Ping Shan Street before stopping for lunch at a café in the trendy hidden neighborhood of PoHo. Then call it a night at the architecturally stunning Peninsula Hong Kong ($900 per night).
The budget-friendly alternative: Chicago
When to go: April to May or September to October, before it gets too hot or too cold
Sample economy airfare: $250 from New York City to Chicago Midway
The allure: Yes, it’s a little gusty, but that may be a small trade-off for access to the Windy City’s world-renowned art, architecture and food scenes (think farm-to-table, tons of bacon and craft beer). “There’s good food everywhere you turn, and beautifully restored neighborhoods where you can walk for hours on end,” Seshadri says.
Areas like Wicker Park and Bucktown are perfect for exploring on foot, and the state-of-the-art Millennium Park is a great place to catch concerts and view public art.
Theater enthusiasts shouldn’t pass up a show at the Steppenwolf Theatre, and for improv and comedy there’s no more storied place than Second City, which has birthed famed performers like Bill Murray, Tina Fey and Steve Carell, to name a few. And history buffs, here’s a challenge: See if you can nab Al Capone’s favorite booth at the well-known jazz and poetry-slam cocktail lounge, The Green Mill.
Finding cool places to lay your head also shouldn’t be a problem: A slew of new spots from the Godfrey Hotel to the upcoming Soho House Chicago are part of the myriad options. Another great stay is the Allegro, which runs just $200 per night.