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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$496 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $496
Expedia
$1,139 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,139
Expedia
$734 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $734
Expedia
$642 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $642
Expedia
$375 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $375
Expedia
$612 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $612
Expedia
$1,121 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,121
Expedia
$844 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $844
Expedia
$608 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $608
Expedia
$733 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $733
Expedia
$951 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $951
Expedia
$679 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $679
Expedia
$777 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $777
Expedia
$681 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $681
Expedia
$1,698 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,698
Expedia
$590 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $590
Expedia
$971 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $971
Expedia
$660 Rosemont, Illinois Rosemont 4-Star Hotel Sale! 3 Nts + Air Fr $660
Expedia
$643 Lombard, Illinois Lombard 4-Star Hotel Sale! 3 Nts + Air Fr $643
Expedia
$89 Schaumburg, Illinois Comfort Suites Schaumburg
Groupon Inc
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
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$217 New York City, New York Cheap Flights from St. Louis
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$185 New York City, New York Cheap Flights from Miami
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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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