No matter what kind of vacation vibe you want to roll with, the Windy City can cater to it.
Whether it's a break jam-packed with iconic sites like the Bean, the Picasso structure or Navy Pier, or a quieter trip to more chilled parts of the city like the North Side’s Andersonville, Chicago keeps the good times rolling.
But with so much on offer, where to start? Listen to the locals, of course. Here are the 10 best ways to experience Chicago like those who know it best – before you know it, you'll be exploring the Windy City like a pro.
When you consider the fact this city is home to the Chicago Cubs (at historic Wrigley Field), the Chicago White Sox (MLB), the Chicago Bears (NFL), the Chicago Bulls (NBA), the Chicago Sky (WNBA), the Chicago Blackhawks (NHL), the Chicago Fire FC and the Chicago Red Stars (NWSL), it’s safe to say this is a sports town.
On any given day, you'll find a sporting event happening, with fans filling up arenas, stadiums and bars, and rooting for their favorite players. Plus, Chicago is one of the rare cities with a long legacy of championships, so don't miss out on the magic of cheering on the hometown team.
Planning tip: Tickets to major games sell out quickly, so buy well in advance if there's a particular one you want. Accommodation prices also shoot up during peak times – book ahead to avoid disappointment.
The Violet Hour is said to be the birthplace of craft cocktails in Chicago, and no visit is complete without a drink here at one of the city’s original speakeasies.
Look for a yellow light to mark the bar’s entrance – if the light is on, they're open for business. Once you cross the threshold, the lights dim, and sound hushes behind towering velvet curtains that open to reveal an upscale cocktail bar. Be sure to keep your phone on silent and dress as if you’re meeting the parents to ensure admittance.
If you can’t get enough of Chicago’s speakeasies, add The Drifter and Lady Bird to your list. The Drifter is located on the lower level of River North’s iconic Green Door Tavern, the city’s oldest drinking hole. Find the entrance en route to the bathroom behind a bookshelf. And the best part? Vaudeville shows play every hour (expect to pay a cover).
Lady Bird is nestled in the basement of the Hoxton, in the West Loop. The low-lit bar features live music (jazz, soul and rock) Thursday through Saturday and evokes feelings of 1960s glam.
Some of the most prominent magicians in the industry reside in Chicago, and i t’s no wonder the city has become a hub for a burgeoning magic scene.
In the Loop, spectators can get dolled up for an intimate night of magic with Dennis Watkins, a third-generation magician, at the opulent Palmer House Hilton – dress well, as cocktail attire
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HotelTonight founder and CEO Sam Shank helped build the fastest and easiest to use hotel booking app in the world — initially focused on guests booking last-minute and same-day hotel rooms, sometimes from the local bar — but he hung around Airbnb for three years and eight months after the short-term rental site acquired the business, and Thursday was his last day there.
Five hours after leaving Chicago, we ran out of pavement. At the tip of the Door Peninsula in northeastern Wisconsin, the ice cream parlors disappeared. The wine shops and art galleries, too. Just a simple tollbooth, and the breakwaters beyond, and a small archipelago gathered like clouds on the horizon. A grinning crewman waved us aboard a 92-ton ferry, and before my wife, Mel, and I could exit our car, the Arni J. Richter was plowing through Lake Michigan. Like us, it seemed eager to flee the crowds.
The American Express® Green Card, with valuable bonus categories and a strong collection of benefits, has the highest welcome offer we've seen publicly available — but it's ending soon.
It'll soon be easier for New York residents to swap snow for sunshine this coming winter. Starting Nov. 10, Delta Air Lines will be launching new routes from New York's Westchester County Airport (HPN) to Orlando and West Palm Beach, the carrier confirmed toTravel + Leisure on Tuesday.
Famous for its blustery winters, steamy summers and skyscraping skyline, Chicago sees the full range of seasons. But thanks to a calendar packed with festivals and events, a rich foodie scene and a full hand of world-class museums to duck into when the days get cold, there's always something happening in the Windy City no matter what month you visit.
Green fields and hills give Ireland its “Emerald Isle” nickname. But with nearly 2,000 miles of coastline, rivers, and lakes, the island nation is also awash in blue. Rounding out all that unspoiled nature are ancient castles, historic villages, and pubs alive with traditional music. Here’s the best way to experience this colorful corner of Europe.
Airlines are pushing boundaries to connect far-flung global cities every year. The longest flight in the world, currently flown by Singapore Airlines, is proof. For travelers who want to visit loved ones—not to mention frequent fliers looking for new ways to earn and burn miles and points—this 19-hour journey from John F. Kennedy is a gem in the crown of ultra-long-haul travel. But even in first and business class, the prospect of such a long journey can be daunting.