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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$615 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $615
Expedia
$896 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $896
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$1,291 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $1,291
Expedia
$387 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $387
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$948 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $948
Expedia
$1,137 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,137
Expedia
$1,837 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,837
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$993 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $993
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$1,912 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,912
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$440 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $440
Expedia
$1,274 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,274
Expedia
$1,024 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,024
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$759 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $759
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$579 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $579
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$601 Lombard, Illinois Lombard 4.5-Star Hotel Sale! 3 Nts + Air Fr $601
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$786 Northbrook, Illinois 4-Star Northbrook Sale! 3 Nts + Air Fr $786
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$896 Rosemont, Illinois Rosemont 4-Star Hotel Sale! 3 Nts + Air Fr $896
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$766 Rosemont, Illinois Rosemont 3.5-Star Hotel Sale! 3 Nts + Air Fr $766
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$431 Schaumburg, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Schaumburg Fr $431
Expedia
$578 Normal, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Normal Fr $578
Expedia
PRICEDESTINATIONDEAL
$217 Philadelphia, Pennsylvania American Airlines Fall & Winter Travel Deals
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$80 Philadelphia, Pennsylvania Cheap Flights from Atlanta
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$217 Philadelphia, Pennsylvania American Airlines Fall & Winter 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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