Sophisticated Chicago


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.

Our travel editors handpicked the dreamiest destinations, hotels, and experiences to curate this series of customized itineraries. Inspired by you. Curated by us.

Book this itinerary today by calling 800-989-1862.

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The world is a wild, wonderful place. Full of life and awaiting discovery. It begs to be explored. And that’s exactly what you can do as a member of Travel + Leisure Club. Join now and enhance this trip with preferred pricing. Plus, gain access to your very own customized concierge and enjoy savings on future trips, too. This is inspiration made real. And it’s all yours.


Personalize your Experience:
Tour the Chicago Highlights A VIP Tour of the Art Institute of Chicago Early Access to the Field Museum of Natural History
Accommodations starting at: $175 per night
Club Member Preferred Pricing starting at: $154 per night
Join our Travel + Lesiure Club with a free 30-day trial and enjoy:

Exclusive Experiences


Customized Concierge


Preferred Pricing

OFFER DETAILS: Prices will vary depending on occupancy, length of stay, itinerary options selected and date availability. Itineraries only available through reservations line 1-800-989-1862. Travel + Leisure Club pricing available only to active Travel + Leisure Club members. 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.

COVID-19 Travel Alert: Please remember to check government advisories before booking and traveling.

California Seller of Travel Reg. No. 21414-50. Registration as a Seller of Travel does not constitute approval by the State of California. Fla. Seller of Travel Reg. No. ST-35519. Washington Seller of Travel Reg. No. 603-338-177. 

HI TAT Broker ID: TA-075-433-7792-01