Hang out at the hip AAA 4-Diamond W Chicago - City Center for $109 a night this winter. This special also includes an upgraded room -- for a savings of 50% on current pricing.

Stay Thursday-Sunday nights through February. Discounted valet parking is $30 with this deal, which is a $55 value. Guests can also upgrade to a larger room on a higher floor of the hotel for $30 more.

The hotel is two blocks from the iconic Willis Tower (formerly the Sears Tower). It is also within walking distance to the Theater District, Millennium Park, the Art Institute of Chicago and shopping on State Street.

Note: Rate is prepaid and nonrefundable.

Not available on: Dec. 30-31, Jan. 1, 22

Travelzoo Tip: The W offers a complimentary car service in the city with the Acura Experience so guests can save on cab fare and arrive at their destination in style.