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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$1,559 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,559
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$3,032 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $3,032
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$893 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $893
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$1,383 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,383
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$678 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $678
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$1,197 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $1,197
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$1,184 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,184
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$802 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $802
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$1,073 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,073
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$1,284 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,284
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$1,164 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,164
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$1,316 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,316
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$958 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $958
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$595 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $595
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$2,657 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,657
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$865 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $865
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$537 Lombard, Illinois Save at 4.5-Star Hotel: 3 Nts + Air to Lombard Fr $537
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$722 Deerfield, Illinois 3.5-Star Deerfield Sale! 3 Nts + Air Fr $722
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$943 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $943
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$545 Bloomington, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Bloomington Fr $545
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PRICEDESTINATIONDEAL
$123 Philadelphia, Pennsylvania Cheap Flights from Orlando
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$49 Philadelphia, Pennsylvania Frontier Airlines Fall Travel Deals
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$143 Philadelphia, Pennsylvania Cheap Flights from Boston
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Chicago Travel Tips

A shiny metropolis where complete strangers ask you if you need directions? Only in the Midwest. Take in loads of friendliness, not to mention cool architecture and major museums.
  • It's a great view … if you're a girl. One of the best views of the city is from the ladies' room in the Hancock Building's Signature Lounge. Tough luck, gentlemen.
  • You can make your mark, just don't use profanity. Gino's East Pizza bakes pies-to-die-for and features patron-placed graffiti all over its walls and tables.
  • Fond o' fondue, are you? Us too. Visit Geja's Cafe in Lincoln Park, a romantically-lit grotto with an astounding array of dip-able dining that also features flamenco and classical guitarists.
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