Chicago may be called the Second City, but this Travel + Leisure World’s Best Award winner is second to none when it comes to great American metropolises. Blessed with magnificent architecture, world-class museums, award-winning restaurants, and some of the best shopping on the planet, this wide and varied city made up of 77 unique neighborhoods has no shortage of things to do and sights to see.

Planned Activities


A pink taxi outside of The Langham in Chicago, Illinois.


from $175 /night

Chicago, Illinois

  • World's Best
Tucked away behind a 1920s-era Art Deco facade in the heart of the Gold Coast neighborhood, the Viceroy Chicago is a Travel + Leisure World’s Best Awards winner for its combination of historic architecture and stunning contemporary design. Glamorous guest rooms feature upscale retro furniture and floor-to-ceiling windows with panoramic views of the city. A rooftop lounge, Devereaux, is the perfect place to pair cocktails with the city’s inimitable skyline. You could take the house Tesla out for a spin around town, but all the best spots, from the Magnificent Mile to the Loop, are within walking distance — including legendary deep-dish pizzeria, Lou Malnati’s, right next door.
A hotel rooftop pool overlooking Chicago, Illinois.


from $423 /night

Chicago, Illinois

  • World's Best
  • City
  • Historic Sites
History and glamour come together flawlessly at The Langham, Chicago, a Travel + Leisure World’s Best Award-winning hotel located on the first 13 floors of famed architect Mies van der Rohe’s iconic IBM building. Mid-century details abound — including original travertine walls and 22-foot-high ceilings — but contemporary art and modern details keep the riverfront property firmly rooted in the present day. The Chuan Spa is just the place to unwind after a long day of sightseeing, while afternoon tea at the Pavilion restaurant is a proper affair reminiscent of the royal service that first launched at the Langham, London, in 1865.

Prices will vary depending on occupancy, availability, length of stay, and itinerary options selected. Itineraries are only available through the reservations line at 1-833-794-1694. Travel + Leisure GO pricing is only available to active Travel + Leisure GO accounts. Rates are subject to limited availability and may be discontinued without notice. Cannot be combined with any other offer. All monetary amounts are noted in U.S. Dollars unless otherwise noted. Itinerary pricing does not include additional expenses such as airfare, transportation, resort fees, taxes, local fees and other incidental expenses. Blackout dates may apply. Hotel prices displayed are per room, per stay based on the cheapest double room available, inclusive of all taxes and service fees — but exclude any fees payable at or to the hotel. Separate terms & conditions may apply for hotels and activities. Please check individual hotel or airline for details. Valid for new bookings only. Your credit card will be charged the total cost of your reservation at time of booking. No reservation is guaranteed until full payment is received. Void where prohibited by law.

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