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Why Not the Windy City? Fall Deals to Chicago



By Charis Atlas Heelan
October 27, 2006

Fancy some pre-holiday season shopping on Chicago's Magnificent Mile? Or how about an architectural tour of some of the country's most stunning 20th century architecture? Fall is an ideal season to take a trip to the Windy City and take advantage of low season rates on everything from airfare to accommodation.

Conrad Chicago's (tel. 312/645-1500; www.conradhotels.com) "Shop Chicago" package includes overnight accommodation, a $50 gift card and VIP savings passport for Westfield North Bridge shopping mall, $30 for shipping of items within the United States (if you buy so much that you can't possibly lug it all home) and a chocolate infatuation amenity (a selection of custom-made chocolate treats delivered to the room). This package is priced from $205 per room, per night and is available until December 31, 2006.

The Marriott Chicago Midway (tel. 800/721-7033; www.marriott.com) has a selection of featured weekend packages priced from $119 per room, per night. The "Holiday Stay for Breakfast" package includes deluxe accommodations and breakfast for two adults and children age 12 and under. Their "Holiday Shopping Extravaganza" includes deluxe accommodations, breakfast for two adults and children age 12 and under and a gift certificate or coupon for local shopping. Use the promotional code XSP when making reservation online or by telephone. Packages are valid seven days a week until January 31, 2007.  Tax is additional and blackout dates may apply. 

For something smaller scale with a more intimate feel, consider staying at one of Chicago's dozen or so bed and breakfast properties (www.chicago-bed-breakfast.com). For example, a one-bedroom suite at City Scene (www.cityscenebb.com) in Lincoln Park starts from $125 per night and is located close to the Armitage-Halsted Landmark District, which has blocks of fascinating shops and restaurants in nineteenth-century buildings, plus Lincoln Park Zoo is one mile east. Flemish House (www.innchicago.com) in the Gold Coast neighborhood has garden studio rooms in a landmark Victorian building from $145 per night. They generally have a two-night minimum midweek and three-night minimum on weekends but single nights can be availability on request. Discounts are offered for stays of one week or more. The Wicker Park Inn (www.wickerparkinn.com) is located in one of Chicago's hottest neighborhoods for dining, shopping and nightlife. Room rates start at $115 per night. The Inn requires a three-night minimum stay on weekends and two-night minimum stay for weekdays -- one-night stays will be accepted subject to availability.

If you are visiting Chicago within the next two weeks and you are traveling with children, be sure to catch an event or two as part of the Chicago Children's Humanities Festival (www.chfestival.org) which forms part of the Chicago Humanities Festival with a far more serious theme of "Peace and War." From storytelling to puppets, dance to music, there is something for all tastes. Events are either free or only $5. The website has a full calendar of events and activities and the festival runs daily at a variety of venues throughout the city until November 12, 2006.

Want to see the city from a local's perspective? Chicago has joined a few other wonderful tourist-friendly cities (like New York and Melbourne, Australia) in introducing the Chicago Greeter Service (tel. 312/742-1284; www.chicagogreeter.com). For the uninitiated, the Greeter Service offers a free personalized view of Chicago, celebrating its friendly people and its vibrant neighborhoods. Visitors are paired with a volunteer that leads them on a two to four hour walk of any of Chicago's neighborhoods and their favorite attractions. Greeters are volunteer Chicago residents who are enthusiastic about their city and want to share their pride and knowledge with visitors.

Millennium Park (www.millenniumpark.org) is a must visit site when you are in Chicago. It is an award-winning center for architecture, art, music and landscape design -- a green and stainless steel oasis in the middle of the city featuring the work of world-renowned architects and designers. The McCormick Tribune Ice Rink will open its sixth skating season this year on November 15 and will remain open through March 16, 2007, weather permitting. The rink draws more than 100,000 skaters annually and is free. Skate rental is available for $7 and the rink is open daily from 10am until 10pm. Experience Chicago's newest holiday tradition at "Cloud Gate: Caroling: each Friday night from November 24 to December 22, 2006. Each evening at 6pm, the choristers and those singing along will be invited to hold holiday candles. The reflection of the candles will twinkle in the stainless steel of Cloud Gate.

Expedia (www.expedia.com) is currently offering a web fare sale on round-trip flights through American Airlines and American Eagle. Tuesday mornings are the best time to check for new deals as they change weekly and you need to book your flight at least seven days before departure. Best of all, these fares are for weekend (technically long weekend) use. Leave after 7:00 PM on a Friday or anytime on Saturday and return on a Monday or Tuesday. Current sample fares to Chicago include:

  • New York $154
  • Raleigh $164
  • Albuquerque $204
  • Los Angeles $204
  • San Antonio $204
  • Richmond $204

Taxes are additional.

Delta (tel. 800/221-1212; www.delta.com) had some comparably low or even lower airfares for round-trip flights to Chicago during the month of November. I found the following available round-trip fares:

  • Detroit $98
  • New York $138
  • Boston $138
  • Miami $138
  • Houston $178
  • Los Angeles $198

Taxes are additional.

Visit our Illinois Message Boards today to discussion Chicago with fellow travelers.


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Related Information:

  • Trip Dates: Varies per provider
  • Destinations: Chicago
  • Provider: Multiple Providers

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.


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