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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$447 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $447
Expedia
$753 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $753
Expedia
$1,283 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,283
Expedia
$680 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $680
Expedia
$913 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $913
Expedia
$994 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $994
Expedia
$1,845 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $1,845
Expedia
$568 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $568
Expedia
$1,105 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,105
Expedia
$1,407 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,407
Expedia
$1,516 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,516
Expedia
$1,752 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,752
Expedia
$694 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $694
Expedia
$738 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $738
Expedia
$1,175 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,175
Expedia
$1,382 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,382
Expedia
$327 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $327
Expedia
$808 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $808
Expedia
$933 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $933
Expedia
$813 Lombard, Illinois Lombard 4-Star Hotel Sale! 3 Nts + Air Fr $813
Expedia
$1,389 Rosemont, Illinois Rosemont 4-Star Hotel Sale! 3 Nts + Air Fr $1,389
Expedia
$269 Wheeler, Indiana Songbird Prairie Bed and Breakfast
Groupon Inc
$149 Zion, Illinois Illinois Beach Resort & Conference Center
Groupon Inc
PRICEDESTINATIONDEAL
$205 Newark, New Jersey Cheap Flights from Tampa
DealBase.com
$355 Newark, New Jersey Cheap Flights from Portland
DealBase.com
$247 Newark, New Jersey Cheap Flights from Milwaukee
DealBase.com
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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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