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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$1,381 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,381
Expedia
$1,734 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,734
Expedia
$2,155 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,155
Expedia
$2,280 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,280
Expedia
$947 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $947
Expedia
$1,139 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,139
Expedia
$2,072 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,072
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$3,834 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $3,834
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$875 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $875
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$1,160 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,160
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$1,693 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,693
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$2,147 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $2,147
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$689 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $689
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$861 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $861
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$887 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $887
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$968 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $968
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$1,018 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $1,018
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$630 Lombard, Illinois Lombard 4.5-Star Hotel Sale! 3 Nts + Air Fr $630
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$608 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $608
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$534 Deerfield, Illinois Deerfield 3.5-Star Hotel Sale! 3 Nts + Air Fr $534
Expedia
PRICEDESTINATIONDEAL
$243 Philadelphia, Pennsylvania American Airlines Fall Travel Deals
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$112 Philadelphia, Pennsylvania Delta US Fare Sale
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$313 Philadelphia, Pennsylvania American Airlines Fall Travel Deals
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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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