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The Windy City at Warm Prices This Fall and Winter

Temperatures may be falling, but so are the prices when it comes to a Chicago getaway this fall or winter.

Temperatures may be falling, but so are the prices when it comes to a Chicago getaway this fall or winter.

Vacations By Rail (tel. 877/929-7245; has a "Chicago Vacation Rail" package including transportation (Amtrak trains), two-nights accommodation at the three-star Best Western Inn of Chicago and hop-on/hop-off trolley tour of the Loop, State Street, Navy Pier, the Magnificent Mile and Chicago's amazing skyline. Prices start at $233 from Detroit or $297 from Minneapolis (on day trains). From Washington DC, the package is priced from $319, $347 from Denver or $357 from New York (on overnight trains). Sleeping accommodations on overnight trains are available on request and are an additional charge. Prices quoted are off-peak and per person, based on double occupancy and include taxes and fees. Prices are subject to change without notice, and all reservations are based on availability. Add-on options include additional hotel nights, a CityPass (including admission to six Chicago attractions), a Grand Tour and Sears Tower Skydeck entry.

For train tickets alone, when booking directly through Amtrak (tel. 800/872-7245;, use promotional code V648 to get a free second person's ticket for people traveling together on trains to Chicago from cities like Milwaukee, Seattle, Denver, Detroit, Dallas, and most destinations in Missouri and Illinois between now and December 15, 2005 (with a blackout period during the Thanksgiving weekend). This represents huge savings for example on the Denver to Chicago route, that's over $300 saved and from Seattle, over $400 depending on your chosen route. If you are traveling alone (or with a friend), enjoy a 70% discount on several Amtrak trains to Chicago using Amtrak's weekly specials page. These discounts exist on select trains on certain dates in October and November from Washington DC ($39.90), Indianapolis ($9.60) and New York ($41.10). See the website for details and conditions as these deals obviously change on a weekly basis.

1800 Cheap Seats (tel. 800/243-2773; is featuring a special vacation offer to Chicago, Illinois from $459 per person dual occupancy for three-nights hotel, round-trip airfare and car rental (mid-size car). These three-night packages are based on off-peak mid-week travel to Chicago. Holiday blackout dates and other restrictions apply with 14-day minimum advance purchase required. Sample pricing from the following departure cities staying at a choice of the three listed hotels (Cass Hotel/Essex Inn Grant Park/Fairmont Chicago) are as follows:

  • St Louis: $459/$499/$609
  • Atlanta, Denver or Dallas: $489/$529/$639
  • Phoenix: $509/$549/$659
  • Las Vegas: $499/$539/$649
  • Miami or San Francisco: $529/$569/$679
  • Los Angeles: $549/$589/$699
  • New York: $559/$599/$709
  • Seattle: $589/$629/$739

Travelocity ( has an "All That Chicago Jazz" vacation package, which includes a round-trip flight and three-nights accommodation at the Hyatt Regency McCormick Place from $325.

Samples prices for mid week departures to Chicago in November are:

  • Indianapolis or Detroit: $350
  • St Louis: $385
  • Milwaukee: $395
  • Miami, Boston, Seattle or Los Angeles: $419
  • Atlanta, Dallas, Denver or San Francisco: $419
  • New York: $446

American Airlines ( is offering special sale fares for domestic travel, including several discounted deals to Chicago. Travel is valid until February 1, 2006. Net Sample Net SAAver fares to Chicago include:

  • Atlanta: $138
  • Ft. Lauderdale, Ft. Myers, Tampa, Charlotte or Orlando: $158
  • Philadelphia, Miami, Jacksonville, Baltimore or Boston: $178
  • Dallas: $208
  • Pittsburgh, New York, Newark or Houston: $218

Fares shown are valid for travel Tuesday, Wednesday and Saturday. Travel on Monday, Thursday or Friday is available at additional cost (no Sundays). Tickets must be purchased at least seven or 21 days prior to departure, depending on destination. Travel is not valid November 22, 23, 26, 27 and 28 or December 21, 2005 through January 3, 2006 or January 16, 2006. Bookings must be completed by January 11, 2006.

Once you get to the US's "Second City", there's plenty to see and do. The Go Chicago Card ( offers general admission to a large number of Chicago attractions including Gray Line tours (the two-day hop-on/hop-off trolley, the Grand Chicago Tour, the North Side Tour and the South Shore Tour), Chicago Architectural Foundation Walking Tours, Chicago Historical Society Walking Tours, Shoreline Sightseeing Skyline Cruises, The Field Museum, The Art Institute of Chicago, The Notebaert Nature Museum, Chicago Children's Museum, Museum of Contemporary Art, Museum of Science and Industry, Swedish American Museum, Adler Planetarium, Shedd Aquarium, John Hancock Observatory, Frank Lloyd Wright Preservation Society Robie House, Sears Tower Sky Deck and Navy Pier attractions. The Go Chicago Card is currently having a fall travel sale where you can save 15% on a three-day, five-day or seven-day card. The sale ends September 30, 2005 and the offer only good for web site bookings.

The three-day card usually costs $109 ($79 for children 3 to 12) and is now $92 ($67), the five-day is usually $129 ($99), now $109 ($75) and the seven-day is reduced from $149 ($119) to $126 ($101). One and two-day cards day ($49 and $89 respectively) remain at regular price.

If you're considering visiting over Columbus Day weekend, keep in mind that the Chicago Marathon ( is being run on Sunday October 9, 2005, so hotels and the city in general may be busier than usual during the fall season.

For more information about Chicago, visit

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