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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$1,474 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,474
Expedia
$497 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $497
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$656 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $656
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$795 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $795
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$799 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $799
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$940 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $940
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$945 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $945
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$1,284 Chicago, Illinois 4.5-Star Chicago Sale! 3 Nts + Air Fr $1,284
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$1,156 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,156
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$1,015 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,015
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$1,287 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,287
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$2,155 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,155
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$4,250 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $4,250
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$586 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $586
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$608 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $608
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$653 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $653
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$682 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $682
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$705 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $705
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$742 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $742
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$928 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $928
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$1,039 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,039
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$1,086 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,086
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$1,351 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,351
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$1,446 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,446
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$460 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $460
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$597 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $597
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$699 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $699
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$731 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $731
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$803 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $803
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$827 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $827
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$876 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $876
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$981 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $981
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$1,043 Deerfield, Illinois 3.5-Star Deerfield Sale! 3 Nts + Air Fr $1,043
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$758 Rosemont, Illinois 4.5-Star Rosemont Sale! 3 Nts + Air Fr $758
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$582 Rosemont, Illinois Rosemont 4-Star Hotel Sale! 3 Nts + Air Fr $582
Expedia
$728 Bloomington, Illinois Bloomington 3.5-Star Hotel Sale! 3 Nts + Air Fr $728
Expedia
PRICEDESTINATIONDEAL
$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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$177 Philadelphia, Pennsylvania Cheap Flights from Dallas
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$97 Philadelphia, Pennsylvania Cheap Flights from Atlanta
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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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