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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$490 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $490
Expedia
$726 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $726
Expedia
$815 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $815
Expedia
$1,366 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,366
Expedia
$1,584 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,584
Expedia
$876 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $876
Expedia
$375 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $375
Expedia
$583 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $583
Expedia
$1,804 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,804
Expedia
$839 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $839
Expedia
$1,733 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,733
Expedia
$680 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $680
Expedia
$1,143 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,143
Expedia
$1,187 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,187
Expedia
$1,847 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,847
Expedia
$444 Lombard, Illinois 4-Star Lombard Sale! 3 Nts + Air Fr $444
Expedia
$812 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $812
Expedia
$848 Schaumburg, Illinois 3.5-Star Schaumburg Sale! 3 Nts + Air Fr $848
Expedia
$812 Bloomington, Illinois 3.5-Star Bloomington Sale! 3 Nts + Air Fr $812
Expedia
$89 Schaumburg, Illinois Comfort Suites Schaumburg
Groupon Inc
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$217 New York City, New York Cheap Flights from St. Louis
DealBase.com
$185 New York City, New York Cheap Flights from Miami
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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