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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$398+ Chicago, Illinois $398+: JW Marriott Chicago Couples' Getaway
JW Marriott Chicago
$362 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $362
Expedia
$59 Chicago, Illinois Hotel Rush
Groupon Inc
$661 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $661
Expedia
$106 Chicago, Illinois Ray's Bucktown Bed and Breakfast
Groupon Inc
$1,202 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,202
Expedia
$74 Chicago, Illinois The Congress Plaza Hotel
Groupon Inc
$867 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $867
Expedia
$104 Chicago, Illinois Thompson Chicago
Groupon Inc
$1,639 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,639
Expedia
$75 Chicago, Illinois Warwick Allerton Hotel Chicago
Groupon Inc
$2,113 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $2,113
Expedia
$461 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $461
Expedia
$1,027 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,027
Expedia
$507 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $507
Expedia
$1,877 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $1,877
Expedia
$1,367 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,367
Expedia
$527 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $527
Expedia
$1,857 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $1,857
Expedia
$576 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $576
Expedia
$95 Evanston, Illinois The Homestead
Groupon Inc
$357 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $357
Expedia
$476 Lombard, Illinois 3.5-Star Lombard Sale! 3 Nts + Air Fr $476
Expedia
$74 Loves Park, Illinois Cliffbreakers Riverside Resort
Groupon Inc
$49 Normal, Illinois The Chateau Hotel & Conference Center
Groupon Inc
$89 Springfield, Illinois The State House Inn
Groupon Inc
$57 Techny, Illinois Wyndham Glenview Suites
Groupon Inc
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$178 New York City, New York Cheap Flights from Tampa
DealBase.com
$221 New York City, New York United Winter Fare Sale
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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