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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$635 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $635
Expedia
$742 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $742
Expedia
$5,132 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $5,132
Expedia
$805 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $805
Expedia
$1,031 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,031
Expedia
$1,091 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,091
Expedia
$1,139 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,139
Expedia
$1,387 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,387
Expedia
$2,322 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,322
Expedia
$2,614 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,614
Expedia
$1,111 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,111
Expedia
$1,318 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,318
Expedia
$849 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $849
Expedia
$858 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $858
Expedia
$907 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $907
Expedia
$2,027 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $2,027
Expedia
$542 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $542
Expedia
$129 Downers Grove, Illinois Sybaris - Downers Grove, IL
Groupon Inc
$565 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $565
Expedia
$1,267 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $1,267
Expedia
$935 Bloomington, Illinois 3.5-Star Bloomington Sale! 3 Nts + Air Fr $935
Expedia
SAVE United States Starwood air/hotel packages from United Vacations®
United Vacations
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$288 New York City, New York Cheap Flights from Salt Lake City
DealBase.com
$303 New York City, New York Cheap Flights from Portland
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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