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Chicago, IL Vacation Deals

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Chicago, IL Vacation Deals

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TYPE PRICE DESTINATION DEAL
$714 Chicago, Illinois Super Savings on Chicago 3 Nts Htl + Air Fr $714
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$601 Chicago, Illinois Top Vacation Sale! 2 Nts + Air as Low as $601
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$723 Chicago, Illinois Don't Miss This: Chicago's Essex Inn 3 Nts + Air Fr $723
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$577 Chicago, Illinois 3% OFF Sofitel Chicago Water Tower! 2 Nts + Air Fr $577
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$647 Chicago, Illinois Don't Miss This: BEST WESTERN Grant Park 3 Nts + Air Fr $647
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$737 Chicago, Illinois Super Sale! 3 Nts Sheraton Chicago and Towers + Air Fr $737
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$482 Chicago, Illinois Save on Your Vacation: 2 Nts ACME Company Chicago + Air Fr $482
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$472 Chicago, Illinois Save on Your Vacation: 2 Nts Wyndham Blake Chicago + Air Fr $472
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$482 Chicago, Illinois Last Minute Vacation Sale! 2 Nts Chicago + Air Fr $482
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$799 Chicago, Illinois The Blackstone A Renaissance Biggest Sale! 3 Nts + Air Fr $799
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$914 Chicago, Illinois Unbelievable Price! 2 Nts The Peninsula Chicago + Air Fr $914
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$682 Chicago, Illinois Last Minute Vacation Sale! 2 Nts Chicago + Air Fr $682
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$2,987 Chicago, Illinois Last Minute Vacation Sale! 8 Nts Chicago + Air Fr $2,987
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$714 Chicago, Illinois Chicago 4-Star Hotel Sale! 4 Nts + Air Fr $714
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$1,410 Chicago, Illinois 15% OFF Chicago Marriott O'Hare! 4 Nts + Air Fr $1,410
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$2,548 Chicago, Illinois 5% OFF Monaco Chicago - a Kimpton! 8 Nts + Air Fr $2,548
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$1,345 Chicago, Illinois Look no Further! Chicago 4 Nts + Air as Low as $1,345
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$1,267 Chicago, Illinois Look no Further! Chicago 4 Nts + Air as Low as $1,267
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$699 Chicago, Illinois Look no Further! Chicago 7 Nts + Air as Low as $699
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$797 Chicago, Illinois Top Vacation Sale! 3 Nts + Air as Low as $797
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$1,958 Chicago, Illinois Look no Further! Chicago 8 Nts + Air as Low as $1,958
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$1,941 Chicago, Illinois Look no Further! Chicago 8 Nts + Air as Low as $1,941
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$1,788 Chicago, Illinois 2% OFF Holiday Inn Chicago - Mart Plaza! 8 Nts + Air Fr $1,788
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$830 Chicago, Illinois Super Sale! 4 Nts The Whitehall + Air Fr $830
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$583 Chicago, Illinois 32% OFF Hyatt Regency McCormick Place! 3 Nts + Air Fr $583
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$723 Chicago, Illinois 15% OFF Millennium Knickerbocker Chicago! 3 Nts + Air Fr $723
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$767 Chicago, Illinois Look no Further! Chicago 3 Nts + Air as Low as $767
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$1,888 Chicago, Illinois 2% OFF Park Hyatt Chicago! 4 Nts + Air Fr $1,888
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$1,440 Chicago, Illinois Super Sale! 4 Nts The James Chicago + Air Fr $1,440
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$1,992 Chicago, Illinois Unbelievable Price! 8 Nts JW Marriott Chicago + Air Fr $1,992
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$1,242 Chicago, Illinois Chicago on Sale! 4 Nts + Air as Low as $1,242
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$732 Chicago, Illinois Super Savings on Chicago 3 Nts Htl + Air Fr $732
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$1,063 Chicago, Illinois Super Sale! 4 Nts Hilton Chicago O'Hare Airport + Air Fr $1,063
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$1,119 Chicago, Illinois 14% OFF Renaissance Chicago O'Hare Suites! 4 Nts + Air Fr $1,119
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$864 Chicago, Illinois Look no Further! Chicago 4 Nts + Air as Low as $864
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$455 Arlington Heights, Illinois Top: Arlington Heights Sale! 4 Nts + Air as Low as $455
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$1,141 Des Plaines, Illinois Des Plaines on Sale! 4 Nts + Air as Low as $1,141
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$600 Bloomingdale, Illinois Bloomingdale 3.5-Star Hotel Sale! 4 Nts + Air Fr $600
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$1,101 Itasca, Illinois Look no Further! Itasca 4 Nts + Air as Low as $1,101
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$681 Bridgeview, Illinois Dream Deal: Super 8 Bridgeview/Chicago Area 4 Nts + Air Fr $681
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$1,229 Rosemont, Illinois 12% OFF The Westin O'Hare! 4 Nts + Air Fr $1,229
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$475 Downers Grove, Illinois Dream Deal: Comfort Inn Downers Grove 4 Nts + Air Fr $475
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$1,136 Rosemont, Illinois Up to 14% OFF on Rosemont 4 Nts Htl + Air Fr $1,136
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$596 Glenview, Illinois 3.5-Star Glenview Sale! 4 Nts + Air Fr $596
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$1,110 Rosemont, Illinois 14% OFF Hilton Rosemont / Chicago O'Hare! 4 Nts + Air Fr $1,110
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$441 Glenview, Illinois Unbeatable Price: 4 Nts Travelodge Glenview + Air Fr $441
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$1,124 Rosemont, Illinois Super Savings on Rosemont 4 Nts Htl + Air Fr $1,124
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$446 Schiller Park, Illinois Incredible Savings: 4 Nts O'Hare Inn & Suites + Air Fr $446
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$1,106 Rosemont, Illinois Super Sale! 7 Nts Chicago Marriott Suites O'Hare + Air Fr $1,106
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$1,165 Rosemont, Illinois Last Minute Vacation Sale! 4 Nts Rosemont + Air Fr $1,165
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$1,036 Rosemont, Illinois Up to 16% OFF on Rosemont 4 Nts Htl + Air Fr $1,036
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$1,124 Rosemont, Illinois Super Sale! 4 Nts Crowne Plaza Chicago O'Hare + Air Fr $1,124
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$1,064 Schiller Park, Illinois Super Savings on Schiller Park 4 Nts Htl + Air Fr $1,064
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$1,008 Schiller Park, Illinois 16% OFF Candlewood Suites Chicago O'Hare! 4 Nts + Air Fr $1,008
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$1,139 Wood Dale, Illinois 15% OFF Courtyard Chicago Wood Dale/Itasca! 4 Nts + Air Fr $1,139
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$472 Naperville, Illinois Travel for Less! 4 Nts BEST WESTERN Naperville Inn + Air Fr $472
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$1,140 Rosemont, Illinois 12% OFF Hyatt Regency O'Hare! 4 Nts + Air Fr $1,140
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$750 Oak Forest, Illinois Top: Oak Forest Sale! 4 Nts + Air as Low as $750
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$1,188 Rosemont, Illinois Super Savings on Rosemont 4 Nts Htl + Air Fr $1,188
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$974 Elk Grove Village, Illinois Up to 15% OFF on Elk Grove Village 4 Nts Htl + Air Fr $974
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$351 O'Fallon, Illinois Dream Deal: Days Inn O'Fallon 4 Nts + Air Fr $351
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$699 Fairview Heights, Illinois Up to 8% OFF on Fairview Heights 7 Nts Htl + Air Fr $699
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$501 Glendale Heights, Illinois Up to 17% OFF on Glendale Heights 7 Nts Htl + Air Fr $501
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$1,157 Itasca, Illinois Itasca on Sale! 4 Nts + Air as Low as $1,157
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$1,106 Rosemont, Illinois Last Minute Vacation Sale! 4 Nts Rosemont + Air Fr $1,106
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$1,163 Rosemont, Illinois Top Vacation Sale! 4 Nts + Air as Low as $1,163
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$1,091 Rosemont, Illinois Super Savings on Rosemont 4 Nts Htl + Air Fr $1,091
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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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