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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$965 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $965
Expedia
$597 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $597
Expedia
$1,413 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,413
Expedia
$4,234 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $4,234
Expedia
$1,243 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,243
Expedia
$680 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $680
Expedia
$1,315 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,315
Expedia
$612 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $612
Expedia
$719 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $719
Expedia
$411 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $411
Expedia
$770 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $770
Expedia
$840 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $840
Expedia
$3,225 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $3,225
Expedia
$680 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $680
Expedia
$1,457 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,457
Expedia
$681 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $681
Expedia
$2,042 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,042
Expedia
$634 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $634
Expedia
$967 Rosemont, Illinois 3.5-Star Rosemont Sale! 3 Nts + Air Fr $967
Expedia
$676 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $676
Expedia
$585 Bloomington, Illinois Bloomington 3.5-Star Hotel Sale! 3 Nts + Air Fr $585
Expedia
$129 Downers Grove, Illinois Sybaris - Downers Grove, IL
Groupon Inc
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
$235 New York City, New York Cheap Flights from Houston
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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