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Chicago, IL

Next Top 20 release: Wednesday, February 10, 2010

Travel dates: Through Nov. 19

Update (Tuesday, August 26, 2008): This offer has either sold out due to huge demand or is no longer available at the originally advertised price, terms and conditions. Click here to see the entire Top 20 list.

By Michael Hicks
Travelzoo Staff

The only thing our Chicago office loves more than seeing the Cubs in first place is this amazing selection of fares on Orbitz to and from the Windy City this fall.  Fly for as little as $98 roundtrip on many dates through Nov.19.

Here are our favorite (roundtrip) fares to/from Chicago:

• Pittsburgh ... $98
• Miami ... $119
• Fort Myers ... $119
• Nashville ... $138
• Baltimore ... $144
• Orlando .. $166
• Long Island ... $176
• Albuquerque ... $178
• Seattle ... $186
• San Diego ... $203
• San Juan, Puerto Rico ... $208

Some of the deals are more widely available than others, so be flexible with your dates when looking for the lowest price.  The best fares are usually available when flying Monday-Thursday and Saturday. 

Don't wait to book.  These fares are unadvertised, which means they could disappear at any time.  

Click here to begin a flexible dates search on Orbitz.  We suggest using Option No. 2 to see whether leaving a few days earlier or later will help you save even more. Note: The price displayed by the Orbitz search is the "out the door" price and will include $20-$50 in taxes.  

Travelzoo Tip: Be sure to check out Orbitz Great American Hotel Sale to save up to 30% OFF your hotel stay in Chicago, or around the country.

Orbitz

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