Puerto Rico, Air/3 Nights, From $617
Save more than $200 on a beachfront resort on the northwestern side of the island.
Hilton Garden Inn Chicago, $89
A discounted one-night stay at the downtown hotel starts at $89 per room per night, based on double occupancy. When: Through Mar. 31, 2007 (Blackout dates: Nov. 24-Dec. 2, Dec. 31, Feb. 21-27, Mar. 12-13, Mar. 22-25) Details: Hotel taxes are an additional 15.4 percent. Book by Nov. 17 Contact: 877/782-9444, hiltongardeninn.com
The Tremont Hotel, $105
The tour operator Leisure Link International has discounted rates for four hotels in the Windy City. For instance, a one-night stay at the historic Tremont Hotel near North Michigan Avenue starts at $105 per room per night, based on double occupancy. When: Dec. 16-31; add $4 for Dec. 3-7 and Dec. 10-14; $20 for Nov. 24, Dec. 1-2, Dec. 8-9, Dec. 15 Details: Hotel taxes are an additional 15.4 percent Contact: 888/801-8808, eleisurelink.com
Conrad Chicago, $205
The Shop Chicago package includes a one-night stay, a $50 gift card and a VIP savings passport for Westfield North Bridge shopping mall, $30 for shipping of items within the United States, and a selection of chocolate treats. Rates start at $205 per room per night, based on double occupancy. When: Through Dec. 31 Details: Hotel taxes are an additional 15.4 percent Contact: 312/645-1500, conradhotels1.hilton.com
The James Chicago Hotel, $289
The Explore package includes a one-night stay, two classic cocktails at the hotel bar or in your room, a copy of the Not for Tourists guide to Chicago, two VIP tickets for express entry to the Museum of Contemporary Art (where suggested admission is $10 per person), and a copy of the museum's coffee-table book. Rates start at $289 per room per night, based on double occupancy. When: Through Dec. 30 Details: Hotel taxes are an additional 15.4 percent Contact: 877/JAMES-55, jameshotels.com
Plus, here are some of our year-round favorite affordable digs: Wicker Park Inn, a cozy 1890s row house whose rates start at $115; Gold Coast Guesthouse B&B in a chichi neighborhood, where rooms start at $119; and the antique-filled City Scene B&B in Lincoln Park, starting at $125. All rates are per room per night.
Getting to Chicago: The lowest round-trip fares we've found for early December are: $102 from New York City (Air Tran); $139 from Fort Lauderdale (American); $174 from Houston (American); $219 from Seattle (American); $246 from Los Angeles (Continental).
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