Give the gift of choice and let someone experience Chicago's architectural legacy with a one or two night stay inside one of the city's most storied landmark buildings.

This exclusive Chicago hotel package allows your recipient to select from a handpicked collection of hotels housed in buildings shaped by Sullivan, Burnham, and their era — offering the perfect blend of skyline views, historic grandeur, and personalized comfort.

From the Venetian Gothic facade of the Chicago Athletic Association to the Art Deco crown of Pendry Chicago, this stay is all about waking up inside a piece of the Windy City's skyline. Whether it's for a spontaneous getaway, a celebration, or simply a well-deserved break, this one or two night experience delivers architecture, atmosphere, and an unforgettable perspective on Chicago's iconic skyline.

Any restrictions to participate?

• Age: Must be 18 years old or older to check in to hotel.

Who can you accommodate for?

• Pets: Most hotels do not allow pets, but be sure to check with the individual hotel if you’d like to bring a pet.

What to expect on the day of the experience?

• What’s included:

  • Enjoy a one or two night stay from a curated selection of hotels.
  • Your stay includes a well-appointed room featuring modern amenities, ensuring a peaceful night's sleep.
  • Immerse yourself in the city, with our handpicked hotels’ prime locations, making it easy to explore nearby attractions, restaurants, and more.
  • Enjoy full access to the hotel’s facilities, which can include, but are not guaranteed at every hotel: a fitness center, spa, and other recreational amenities for a complete and rejuvenating experience.
  • Choose any desired date for this delightful escape, and we'll take care of everything to ensure the stay is truly unforgettable. Keep in mind that rates and availability may vary per day.
  • Please note that flights and travel arrangements are not included.

• Check in/ check out: Times will vary based the hotel chosen. Please verify in advance the specific check in/out times of the hotel you have selected.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the hotel is booked.